# Bing Crosby discography

American singer Bing Crosby has released 71 studio albums, 307 compilation albums and 409 singles over the course of his career. Crosby is one of the world's best-selling music artists, having sold more than 200 million records as of 1960 according to different sources his sales could be 300 million, 500 million records, tapes, compact discs and digital downloads globally. Guinness World Records recognizes "White Christmas" as the best-selling single of all time, selling 50 million copies globally.
Crosby was an influence on multimedia stars that followed, including Elvis Presley. Musically, Crosby set the benchmark for the intimate "easy listening" genre that influenced future male artists including Frank Sinatra, Dean Martin, Perry Como, and Dick Haymes. He first started recording in 1926 with Don Clark and his Hotel Biltmore Orchestra, when he sang the vocal refrain on "I've Got the Girl". He joined the Paul Whiteman Orchestra in 1927 which led to his first screen appearance as a member of the trio The Rhythm Boys in King of Jazz.
He released his first album containing compilations in 1939, and his first studio album Ballad for Americans, (which contained no re-issued singles) in 1940. His final album Beautiful Memories was recorded in 1976; however, material recorded before his death was issued posthumously in 1977 as the album Seasons. Crosby recorded with numerous artists, including Al Jolson, his fellow film stars Judy Garland and Bob Hope, and The Andrews Sisters.

## Lifetime albums (studio and compilations)

| Year | Album | Label | Peak chart position | Certifications |
| 1939 | Music of Hawaii (compilation) | Decca | — | |
| 1939 | Victor Herbert Melodies, Vol. 1 (recorded in 1938) | Decca | — | |
| 1939 | Patriotic Songs for Children (compilation) | Decca | — | |
| 1939 | Cowboy Songs (Bing Crosby's first solo album - compilation) | Decca | — | |
| 1939 | Victor Herbert Melodies, Vol. 2 | Decca | — | |
| 1939 | George Gershwin Songs, Vol. 1 (compilation) | Decca | — | |
| 1940 | Ballad for Americans (Bing Crosby's first solo studio album) | Decca | — | |
| 1940 | Favorite Hawaiian Songs | Decca | — | |
| 1940 | Decca Presents an Album of Christmas Music (compilation) | Decca | — | |
| 1940 | Star Dust | Decca | 10 (reissue) | |
| 1941 | Hawaii Calls | Decca | — | |
| 1941 | Small Fry | Decca | — | |
| 1941 | Crosbyana (compilation) | Decca | — | |
| 1941 | Under Western Skies | Decca | — | |
| 1942 | Song Hits from Holiday Inn | Decca | — | |
| 1942 | A Collection Of Early Recordings Volume 1 (compilation) | Brunswick | — | |
| 1944 | Crosby Classics (compilation) | Columbia Masterworks | — | |
| 1944 | A Collection Of Early Recordings Volume 2 (compilation) | Brunswick | — | |
| 1945 | Merry Christmas (box set versions of 45's were available by the '50s) | Decca | 1 | RIAA: Gold |
| 1945 | Selections from Going My Way | Decca | 1 | |
| 1946 | Selections from The Bells of St. Mary's (recorded in 1945) | Decca | 1 | |
| 1946 | Don't Fence Me In (w/ The Andrews Sisters) | Decca | 2 | |
| 1946 | The Happy Prince | Decca | — | |
| 1946 | Selections from Road to Utopia (recorded in 1944) | Decca | — | |
| 1946 | Bing Crosby - Stephen Foster | Decca | — | |
| 1946 | What We So Proudly Hail | Decca | — | |
| 1946 | Favorite Hawaiian Songs, Vol. One | Decca | — | |
| 1946 | Favorite Hawaiian Songs, Vol. Two | Decca | — | |
| 1946 | Blue Skies (w/ Fred Astaire and Irving Berlin) | Decca | 2 | |
| 1946 | Bing Crosby - Jerome Kern | Decca | — | |
| 1947 | St. Patrick's Day | Decca | 1 | |
| 1947 | Bing Crosby – Victor Herbert | Decca | — | |
| 1947 | Cowboy Songs, Vol. One | Decca | — | |
| 1947 | Selections from Welcome Stranger (recorded in 1946) | Decca | — | |
| 1947 | Our Common Heritage | Decca | — | |
| 1947 | El Bingo - Latin American Favorites | Decca | — | |
| 1947 | The Small One | Decca | — | |
| 1947 | The Man Without a Country | Decca | — | |
| 1947 | Drifting and Dreaming | Decca | — | |
| 1947 | St. Valentine's Day (compilation) | Decca | 8 | |
| 1948 | Blue of the Night | Decca | — | |
| 1948 | Selections from Showboat | Decca | — | |
| 1948 | Bing Crosby – The Emperor Waltz (recorded in 1947) | Decca | 2 | |
| 1948 | Bing Crosby Sings with Al Jolson, Bob Hope, Dick Haymes and the Andrews Sisters (compilation) | Decca | — | |
| 1948 | Selections from Road to Rio | Decca | — | |
| 1948 | Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer | Decca | — | |
| 1948 | Bing Crosby Sings with Lionel Hampton, Eddie Heywood, Louis Jordan (compilation) | Decca | — | |
| 1948 | Bing Crosby Sings the Song Hits from Broadway Shows (compilation) | Decca | — | |
| 1948 | Cowboy Songs, Vol. Two | Decca | — | |
| 1948 | Auld Lang Syne | Decca | — | |
| 1949 | Bing Crosby Sings Cole Porter Songs | Decca | — | |
| 1949 | A Connecticut Yankee In King Arthur's Court (recorded in 1947) | Decca | 5 | |
| 1949 | Bing Crosby Sings Songs by George Gershwin | Decca | — | |
| 1949 | South Pacific | Decca | 8 | |
| 1949 | Christmas Greetings | Decca | 4 | |
| 1949 | Ichabod – The Legend of Sleepy Hollow | Decca | — | |
| 1949 | Crosby Classics Vol. 2 (compilation) | Columbia | 8 | |
| 1950 | Top o' the Morning / Emperor Waltz (compilation) | Decca | — | |
| 1950 | Songs from Mr. Music (w/ Dorothy Kirsten and The Andrews Sisters - LP and also 45/78 RPM box set versions of this compilation album) | Decca | 10 | |
| 1950 | Go West Young Man (w/ The Andrews Sisters LP and also a 78 RPM box set version of this album) | Decca | — | |
| 1950 | A Crosby Christmas (EP) (w/ Gary Crosby, Phillip Crosby, Dennis Crosby and Lindsay Crosby) | Decca | — | |
| 1950 | Bing Crosby, Collectors' Classics - Vols. 1-8 (set of 8 LPs - also 45 RPM box sets for each of the eight compilation albums) | Decca | — | |
| 1950 | Cowboy Songs Volume 3 (compilation - 45 RPM box set) | Decca | — | |
| 1950 | When Irish Eyes Are Smiling (LP and EP versions, as well as a 45 RPM box set) | Decca | — | |
| 1950 | Bing Crosby Sings the Song Hits from... (LP and also a 45 RPM box set version) | Decca | — | |
| 1950 | Al Jolson And Bing Crosby (LP and also a 45 RPM box set) | Decca | — | |
| 1950 | Down Memory Lane With Bing Crosby Vol. I (LP and also a 45 RPM box set version of this compilation album) | Decca | — | |
| 1951 | Way Back Home (LP and also 45/78 RPM box set versions of this album) | Decca | — | |
| 1951 | Bing and the Dixieland Bands (compilation) | Decca | — | |
| 1951 | Yours Is My Heart Alone (LP and also 45/78 RPM box set versions of this album) | Decca | — | |
| 1951 | Country Style (LP and also a 45 RPM box set version of this album) | Decca | — | |
| 1951 | Beloved Hymns (recorded in 1949 - LP and also 45/78 RPM box set versions of this album) | Decca | — | |
| 1951 | Bing Crosby Sings Victor Herbert Songs (compilation) | Decca | — | |
| 1951 | Down Memory Lane With Bing Crosby Vol. II (LP and also a 45 RPM box set version of this compilation album) | Decca | — | |
| 1952 | Bing and Connee (w/ Connee Boswell - LP and also a 45 RPM box set version of this album) | Decca | — | |
| 1952 | Themes and Songs from The Quiet Man (w/ Victor Young) | Decca | — | |
| 1952 | Selections from the Paramount Picture "Just for You" (w/ Jane Wyman and The Andrews Sisters - LP and also a 45 RPM box set version of this album) | Decca | — | |
| 1952 | Road to Bali (w/ Bob Hope and Peggy Lee - LP and also 45/78 RPM box set versions of this album) | Decca | — | |
| 1953 | Le Bing: Song Hits of Paris | Decca | — | |
| 1953 | Gary Crosby and Friend (EP) (w/ Gary Crosby) | Decca | — | |
| 1953 | Bing Crosby and The Andrews Sisters (EP) (w/ The Andrews Sisters) | Decca | — | |
| 1953 | Bing Crosby Sings Song Hits from The King and I (EP) | Decca | — | |
| 1953 | Bing Sings the Hits | Decca | — | |
| 1954 | Some Fine Old Chestnuts (recorded in 1953) | Decca | — | |
| 1954 | Selections from Irving Berlin's White Christmas (w/ Peggy Lee and Danny Kaye) | Decca | 2 | |
| 1954 | Bing: A Musical Autobiography (17xEP and 5xLP box set compilations) | Decca | 9 | |
| 1954 | The Country Girl / Little Boy Lost (recorded in 1953–1954) | Decca | — | |
| 1955 | Merry Christmas (later version of 1945 78rpm album, later renamed White Christmas in 1995) | Decca | — | RIAA: 4× Platinum BPI: Silver |
| 1955 | Young Bing Crosby (compilation) | RCA Victor, "X" | — | |
| 1955 | Old Masters (box set EP compilation) | Decca | — | |
| 1956 | Shillelaghs and Shamrocks (compilation) | Decca | — | |
| 1956 | Home on the Range (compilation) | Decca | — | |
| 1956 | Blue Hawaii (compilation) | Decca | — | |
| 1956 | High Tor (w/ Julie Andrews and Everett Sloane) (recorded in 1955) | Decca | — | |
| 1956 | A Christmas Sing with Bing around the World (recorded in 1955) | Decca | — | |
| 1956 | Anything Goes (w/ Donald O'Connor, Mitzi Gaynor and Zizi Jeanmaire) | Decca | — | |
| 1956 | Songs I Wish I Had Sung the First Time Around | Decca | — | |
| 1956 | Bing Sings Whilst Bregman Swings | Verve | — | |
| 1956 | High Society (w/ Frank Sinatra, Grace Kelly, and Louis Armstrong) | Capitol | 5 | |
| 1957 | Bing with a Beat | RCA Victor | — | |
| 1957 | A Christmas Story - An Axe, An Apple and a Buckskin Jacket | Golden Records | — | |
| 1957 | Ali Baba and the Forty Thieves | Golden Records | — | |
| 1957 | New Tricks (recorded in 1955–1956) | Decca | — | |
| 1957 | The Bible Story of Christmas | World Library Publications | — | |
| 1957 | Christmas Time (EP) | Decca | — | |
| 1957 | Once Over Lightly (EP) | Decca | — | |
| 1958 | Never Be Afraid (recorded in 1957) | Golden Records | — | |
| 1958 | Jack B. Nimble – A Mother Goose Fantasy (recorded in 1957) | Golden Records | — | |
| 1958 | Fancy Meeting You Here (w/ Rosemary Clooney) | RCA Victor | — | |
| 1958 | Around the World with Bing! | Decca | — | |
| 1958 | Bing in Paris | Decca | — | |
| 1958 | That Christmas Feeling (incorporates the 1949 78rpm album Christmas Greetings, and 5 later recordings) | Decca | — | |
| 1958 | In a Little Spanish Town | Decca | — | |
| 1958 | Crosby Classics (compilation) | Harmony | — | |
| 1958 | A Musical Autobiography of Bing Crosby 1927 - 1934 (compilation) | Decca | — | |
| 1958 | Bing Crosby Sings (compilation) | Vocalion | — | |
| 1959 | Bing’s Buddies and Beaus | Brunswick | — | |
| 1959 | Say One for Me (w/ Debbie Reynolds and Robert Wagner) | Columbia | — | |
| 1959 | A Musical Autobiography of Bing Crosby 1941-1944 (compilation) | Decca | — | |
| 1960 | How the West Was Won (w/ Rosemary Clooney, recorded in 1959) | RCA Victor | — | |
| 1960 | Join Bing and Sing Along (recorded in 1959) | Warner Records / RCA Victor | 7 (UK) | |
| 1960 | Bing & Satchmo (w/ Louis Armstrong) | MGM Records | — | |
| 1960 | Songs of Christmas | Decca | — | |
| 1961 | 101 Gang Songs (recorded in 1960) | Warner Records | — | |
| 1961 | El Señor Bing (recorded in 1960) | MGM Records | — | |
| 1961 | My Golden Favorites | Decca | — | |
| 1961 | A Musical Autobiography of Bing Crosby 1944-1947 (compilation) | Decca | — | |
| 1962 | The Road to Hong Kong | Liberty | — | |
| 1962 | Bing's Hollywood vols.1-15 (set of 15 albums) | Decca | — | |
| 1962 | On the Happy Side | Warner Records | — | |
| 1962 | I Wish You a Merry Christmas | Warner Records | — | |
| 1962 | Holiday in Europe (recorded in 1961) | Decca | — | |
| 1962 | Only Forever (compilation) | Decca | — | |
| 1962 | Easy to Remember (compilation) | Decca | — | |
| 1962 | Accentuate the Positive (compilation) | Decca | — | |
| 1962 | Sunshine Cake (compilation) | Decca | — | |
| 1962 | Swinging on a Star (compilation) | Decca | — | |
| 1962 | Pocket Full of Dreams (compilation) | Decca | — | |
| 1962 | Pennies from Heaven (compilation) | Decca | — | |
| 1962 | But Beautiful (compilation) | Decca | — | |
| 1963 | Guys and Dolls | Reprise | — | |
| 1963 | Finian's Rainbow | Reprise | — | |
| 1963 | South Pacific | Reprise | — | |
| 1964 | Return to Paradise Islands (recorded in 1963) | Reprise | — | |
| 1964 | America, I Hear You Singing (w/ Frank Sinatra and Fred Waring) | Reprise | — | |
| 1964 | Robin and the 7 Hoods (w/ Frank Sinatra, Dean Martin, and Sammy Davis, Jr.) | Reprise | — | |
| 1964 | 12 Songs of Christmas (w/ Frank Sinatra and Fred Waring) | Reprise | — | |
| 1964 | The Very Best of Bing Crosby (compilation) | MGM Records | — | |
| 1965 | Bing Crosby Sings the Great Country Hits (recorded in 1963) | Capitol | — | |
| 1965 | That Travelin' Two-Beat (w/ Rosemary Clooney, recorded in 1964) | Capitol | — | |
| 1965 | Bing Crosby (compilation) | Metro Records | — | |
| 1966 | The Summit (w/ Dean Martin, Frank Sinatra and Sammy Davis Jr.) | Reprise | — | |
| 1966 | Bing Crosby's Treasury – The Songs I Love (6-LP box set - reissued in 1968) | Longines Symphonette Society | — | |
| 1966 | Bing Crosby's All Time Hit Parade (compilation) | Longines Symphonette Society | — | |
| 1966 | Bing Sings for Children (compilation) | Vocalion | — | |
| 1967 | Bing Crosby and The Columbus Boychoir Sing Family Christmas Favorites (w/ The Columbus Boychoir) | Decca | — | |
| 1967 | Bing Crosby in Hollywood (1930-1934) (compilation) | Columbia | — | |
| 1968 | Thoroughly Modern Bing | Pickwick | — | |
| 1968 | Paul Whiteman and His Orchestra Featuring Bing Crosby (compilation) | Columbia | — | |
| 1969 | Hey Jude / Hey Bing! (recorded in 1968) | Amos | — | |
| 1970 | Goldilocks | Disneyland | — | |
| 1971 | A Time to Be Jolly | Daybreak | — | |
| 1971 | The Best of Bing | MCA Records | — | BPI: Silver |
| 1972 | Bing 'n' Basie (w/ Count Basie) | Daybreak | — | |
| 1972 | Rhythm on the Range | Coral | — | |
| 1972 | I’ll Sing You a Song of the Islands | Coral | — | |
| 1972 | Wrap Your Troubles In Dreams (compilation) | RCA Victor | — | |
| 1973 | The Very Best of Bing (mail-order 7-LP box set) | World Records (UK) | — | BPI: Gold |
| 1973 | Soft Lights and Sweet Music (compilation) | Biograph | — | |
| 1973 | Rare Early Recordings 1929-1933 (compilation) | Capitol Records | — | |
| 1973 | Christmas with... Bing Crosby / Nat King Cole / Dean Martin (Christmas compilation) | Pelican Records | — | |
| 1974 | The Bing Crosby Story Volume I: The Early Jazz Years, 1928-1932 (compilation) | Columbia Special Products | — | |
| 1975 | A Southern Memoir | London Records | — | |
| 1975 | That's What Life Is All About | United Artists | 28 (UK) | BPI: Silver |
| 1975 | A Couple of Song and Dance Men (w/ Fred Astaire) | United Artists | — | |
| 1976 | Tom Sawyer (recorded in 1975) | Argo | — | |
| 1976 | At My Time of Life | United Artists | — | |
| 1976 | Bing Crosby Live at the London Palladium | K-tel | 9 (UK) | |
| 1976 | Feels Good, Feels Right | Decca | — | |
| 1977 | Beautiful Memories (recorded in 1976) | United Artists | — | |
| 1977 | Bingo Viejo (recorded in 1975) | London Records / Anahuac | — | |
| 1977 | A Tribute to Duke (also featuring Tony Bennett, Rosemary Clooney, and Woody Herman) | Concord Jazz | — | |
| 1977 | Seasons (Bing Crosby's last studio album released during his lifetime) | Polydor | 25 (UK) | BPI: Silver |

## Posthumous releases and compilations

| Year | Album | Label | Peak chart position | Certifications |
| 1977 | The Greatest Hits of Bing Crosby (M.F. Productions 2 LP) | Jay Norris | — | |
| 1977 | Where the Blue of the Night Meets the Gold of the Sky (Biograph BLP-M-1) | Biograph | — | |
| 1977 | Kraft Music Hall January 29, 1942 | Spokane Records | — | |
| 1977 | Harry Lillis Crosby | Columbia Special Products | — | |
| 1977 | Bing Crosby's Good Time Favorites | Capitol Records | — | |
| 1977 | Remembered | Columbia Special Products | — | |
| 1977 | Bing in the Thirties | Spokane Records | — | |
| 1977 | Bing Crosby Golden Memories (6-LP box set) | Columbia Special Products | — | |
| 1977 | Distinctively Bing, Volume 1 | Sunbeam | — | |
| 1977 | Distinctively Bing, Volume 2 | Sunbeam | — | |
| 1977 | A Legendary Performer | RCA | — | |
| 1977 | White Christmas (Christmas collection - also featuring Rosemary Clooney) | Collector's Gold | — | |
| 1977 | Bing Crosby's Greatest Hits | MCA Records | — | |
| 1977 | Bing Crosby's Christmas Classics (Christmas collection - abridged version of I Wish You a Merry Christmas) | Capitol Records | — | |
| 1977 | Happy Holiday With Frank & Bing (Christmas collection - also featuring Frank Sinatra) | Collector's Gold | — | |
| 1978 | Bing Sings (96 of His Greatest Hits) (8-LP box set) | Reader's Digest Music | — | RIAA: 2× Platinum |
| 1978 | Bing Crosby Happy Holiday (Christmas collection) | Spokane Records | — | |
| 1978 | The Greatest Christmas Shows (Christmas collection) | Fox American | — | |
| 1978 | A Bing Crosby Collection, Volume I | Columbia | — | |
| 1978 | A Bing Crosby Collection, Volume II | Columbia | — | |
| 1979 | A Bing Crosby Collection, Volume III | Columbia | — | |
| 1979 | Swing with Bing | Koala | — | |
| 1979 | Christmas with Bing Crosby and the Harry Simeone Chorale (Christmas collection) | 51 West Records & Tapes | — | |
| 1979 | You Keep Coming Back Like a Song | Koala | — | |
| 1980 | Bing - The Final Chapter | BBC Records | — | |
| 1980 | Christmas with Bing (Christmas collection) | Reader's Digest, RCA Custom | — | |
| 1980 | Bing Sings Again (8-LP box set) | Reader's Digest Music | — | |
| 1980 | Judy And Bing (Mail Call #2) (also featuring Judy Garland) | Tandem Records | — | |
| 1981 | On the Air (also featuring the Music Maids) | Spokane Records | — | |
| 1981 | Bing and Connee on the Air (also featuring Connee Boswell) | Spokane Records | — | |
| 1981 | Music Hall Highlights (with the John Scott Trotter Orchestra) | Spokane Records | — | |
| 1982 | Rare 1930-31 Brunswick Recordings | MCA Records | — | |
| 1983 | Bing & Bob (also featuring Bob Hope) | Spokane Records | — | |
| 1983 | Bing Crosby with Glenn Miller and American Band of the Allied Expediatory Forces Orchestra | Broadway Intermission | — | |
| 1983 | Crosbyana - Volume II "The Fabulous Rice Tapes - 1937" | Broadway Intermission | — | |
| 1983 | Bing's Rare First Broadcast | Frogbien Records | — | |
| 1983 | Havin' Fun! (also featuring Louis Armstrong) | Sounds Rare | — | |
| 1983 | More Fun! (also featuring Louis Armstrong) | Sounds Rare | — | |
| 1984 | Crosby & Como (also featuring Perry Como) | Broadway Intermission | — | |
| 1984 | Crosbyana - Volume III: The War Years | Broadway Intermission | — | |
| 1984 | Christmas with Bing (Christmas collection) | Capitol Records | — | |
| 1984 | Bing in the Thirties - Volume 5 | Spokane Records | — | |
| 1985 | The Radio Years, Volume 1 | GNP Crescendo | — | |
| 1985 | The Radio Years, Volume 2 | GNP Crescendo | — | |
| 1985 | Der Bingle - Volume 4 | Spokane Records | — | |
| 1985 | Christmas Wishes (Christmas collection - also featuring the Hollywood Bowl Symphony Orchestra) | Capitol Records | — | |
| 1985 | Bing in the Thirties - Volume 6 | Spokane Records | — | |
| 1985 | Favorites By Bing Crosby | Capitol Records | — | |
| 1985 | Just for Fun | Broadway Intermission | — | |
| 1985 | Bing Crosby - Legendary Singers | Time Life Music | — | |
| 1986 | Bing Crosby Sings Christmas Songs (Christmas collection) | MCA Records | — | |
| 1986 | Dancing and Reminiscing with Bing Crosby | Reader's Digest Music | — | |
| 1986 | Crosbyana - Volume 5 From Bing's Collection | Broadway Intermission | — | |
| 1986 | The Radio Years, Volume 3 (with Rosemary Clooney, Burl Ives, and Maurice Chevalier ) | GNP Crescendo | — | |
| 1986 | Bing Crosby Sings Again | MCA Records | — | |
| 1986 | White Christmas (Christmas collection) | Metacom, Inc. | — | |
| 1986 | Home Town Christmas (Christmas collection - also featuring Kate Smith) | RCA Special Products | — | |
| 1987 | Tenth Anniversary Collection (3-CD box set) | Warwick Records (UK) | — | BPI: Silver |
| 1987 | Island Magic! / Hawaiian Gold | The Good Music Record Co. | — | |
| 1987 | Lady Of Spain | Golden Circle, Inc. | — | |
| 1987 | Bing Sings Crosby | Broadway Intermission | — | |
| 1987 | White Christmas - Bing Crosby Sings Yuletide Favorites (Christmas collection) | Reader's Digest | — | |
| 1988 | Together Again (also featuring Red Nichols) | Broadway Intermission | — | |
| 1988 | Bing & Dinah (also featuring Dinah Shore) | Spokane Records | — | |
| 1988 | The Crooner: The Columbia Years 1928-1934 (3-CD box set) | Columbia | — | |
| 1988 | His Most Loved Recordings | MCA Records | — | |
| 1988 | Bing Crosby & Rosemary Clooney Christmas (Christmas collection) | MCA Records | — | |
| 1988 | Pennies from Heaven (Christmas collection) | Fanfare, Pro-Arte Digital | — | |
| 1988 | Bing in the Thirties - Volume 7 | Spokane Records | — | |
| 1989 | MacNamara's Band | MCA Special Products | — | |
| 1989 | It's Christmas Time (Christmas collection - also featuring Frank Sinatra and Nat King Cole) | Laserlight Digital | — | |
| 1989 | Love Songs - The Crosby Way | Capitol Special Markets | — | |
| 1989 | Winter Wonderland (Christmas collection - also featuring Nat "King" Cole and Dean Martin) | CEMA Special Markets | — | |
| 1989 | Pocketful Of Dreams | Fanfare | — | |
| 1989 | Christmas (Christmas collection - also featuring Liberace) | MCA Special Products | — | |
| 1990 | The All-Time Best Of Bing Crosby | Curb Records | — | |
| 1990 | The Christmas Songs Featuring War-time Christmas Broadcasts (Christmas collection) | Vintage Jazz Classics | — | |
| 1991 | White Christmas (Christmas collection) | Laserlight Digital | — | |
| 1991 | A Visit To The Movies | Laserlight Digital | — | |
| 1991 | Christmas With Bing Crosby, Nat "King" Cole, Dean Martin (Christmas collection) | One Way Records | — | |
| 1992 | 16 Most Requested Songs | Legacy | — | |
| 1992 | White Christmas and Other Favorites (Christmas collection) | Spirit of Christmas Nelson | — | |
| 1992 | Merry Christmas from Bing Crosby, Nat "King" Cole & Julie Andrews (Christmas collection) | GSC Music | — | |
| 1992 | Mail Call (Armed Forces Radio Broadcasts) (also featuring Judy Garland) | Laserlight Digital | — | |
| 1993 | Bing: His Legendary Years 1931–1957 (4-CD box set) | MCA Records | — | |
| 1993 | Crosby Family Christmas (Christmas collection) | Pilz | — | |
| 1993 | White Christmas (Christmas collection) | Eclipse Music Group | — | |
| 1993 | Christmas with Bing & Frank (Christmas collection - also featuring Frank Sinatra) | Eclipse Music Group | — | |
| 1993 | The Radio Years (single-CD version compiled from the previous three volumes) | GNP Crescendo | — | |
| 1993 | Christmas Classics (Christmas collection) | MCA Records, The Beautiful Music Company | — | |
| 1994 | That Christmas Feeling (Christmas collection - also featuring Frank Sinatra) | Regency Music | — | |
| 1994 | WWII Radio (March 9 and June 29, 1944) | LaserLight Digital | — | |
| 1994 | WWII Radio (July 6 and November 30, 1944) | LaserLight Digital | — | |
| 1994 | WWII Radio (January 8 and 25, 1945) | LaserLight Digital | — | |
| 1994 | WWII Radio (October 7 and December 16, 1943) | LaserLight Digital | — | |
| 1995 | Christmas Through the Years (Christmas collection) | LaserLight Digital | — | |
| 1996 | A Little Bit of Irish (posthumous edition, recorded in 1966) | Atlantic Records, Golden Olden Recordings | — | |
| 1996 | Bing Crosby, Rosemary Clooney & Friends (Christmas collection) | MasterTone | — | |
| 1996 | Live Duets 1947-1949 | Viper's Nest | — | |
| 1996 | My Favorite Country Songs | MCA Special Products | — | |
| 1996 | My Favorite Love Songs | MCA Special Products | — | |
| 1996 | Their Complete Recordings Together (also featuring the Andrew Sisters) | MCA Records, Decca | — | |
| 1996 | Christmas Sing with Frank and Bing (Christmas collection - also featuring Frank Sinatra) | LaserLight Digital | — | |
| 1996 | Top O' the Morning - His Irish Collection (also featuring the Andrew Sisters) | MCA Records, Decca | — | |
| 1997 | Bing's Gold Records - The Original Decca Recordings | MCA Records | — | |
| 1997 | My Favorite Irish Songs | MCA Records | — | |
| 1997 | When Irish Eyes are Smiling / Shillelaghs and Shamrocks | MCA Records | — | |
| 1997 | My Favorite Hawaiian Songs | MCA Special Products | — | |
| 1997 | His Greatest Hits and Finest Performances | Universal Music Special Markets, Reader's Digest Music | — | |
| 1998 | Bing Crosby: The Voice of Christmas (Christmas collection) | MCA Records, Spectrum Music | — | BPI: Silver |
| 1998 | Winter Wonderland (Christmas collection) | EMI Gold (UK) | — | BPI: Silver |
| 1998 | It's Christmas Time (Christmas collection - also featuring Frank Sinatra and Louis Armstrong) | LaserLight Digital | — | |
| 1998 | Silver Bells Of Christmas (Christmas collection - also featuring Rosemary Clooney) | KRB Music Companies | — | |
| 1998 | The Holiday Album (Christmas collection - also featuring Nat King Cole) | Fine Tune | — | |
| 1999 | The Best of Bing Crosby (20th Century Masters – The Millennium Collection) | MCA Records | — | |
| 1999 | Legends of The 20th Century | EMI | — | |
| 1999 | The Very Best of Bing Crosby Christmas (Christmas collection) | MCA Records | — | |
| 1999 | Christmas with Bing Crosby - All-Time Favorites (Christmas collection) | Universal Music Special Markets, GSC Music | — | |
| 1999 | My Favorite Hawaiian Songs | MCA Special Products | — | |
| 1999 | I'll Be Home for Christmas (Christmas collection) | Sleigh Bells | — | |
| 2000 | The Best of the War Years | Stardust Records | — | |
| 2000 | A Merry Christmas with Bing Crosby & the Andrews Sisters (Christmas collection) | MCA Records | — | |
| 2000 | Academy Award Winners & Nominees 1934-1960 | MCA | — | |
| 2001 | Bing Crosby & Friends Christmas Special - featuring Frank Sinatra (Christmas collection) | Park South Records | — | |
| 2001 | Song Hits From The Movies 1930 to 1953 | Nimbus Records | — | |
| 2001 | Christmas with Bing Crosby (Christmas collection) | Lifestyles | — | |
| 2001 | Two Classic Albums from Bing Crosby | Collectors' Choice Music | — | |
| 2001 | Lost Columbia Sides 1928-1933 | Collectors' Choice Music | — | |
| 2001 | Bing Crosby In Hollywood (1930-1934) Volume One | Collectables | — | |
| 2001 | Bing Crosby In Hollywood (1930-1934) Volume Two | Collectables | — | |
| 2001 | Cocktail Hour - Duets | Allegro Corporation, Columbia River Entertainment Group | — | |
| 2002 | The Radio Years (double-CD box set compiled from the earlier three volumes) | GNP Crescendo | — | |
| 2002 | The Bing Crosby Radio Variety Show | Mr Punch Audio | — | |
| 2002 | Christmas with Bing Crosby (Christmas collection) | Universal Music Special Markets, Platinum Legends | — | |
| 2003 | Songs of WWII | Delta | — | |
| 2003 | Bing Crosby Christmas (Christmas collection) | NorthQuest | — | |
| 2003 | A Centennial Anthology of His Decca Recordings | MCA Records | — | |
| 2003 | The Essential Bing Crosby: The Columbia Years | Columbia, Legacy | — | |
| 2004 | Bing Crosby Christmas Collection (Christmas collection) | PolyGram Group Distribution, Inc. | — | |
| 2004 | Swingin' with Bing, Bing Crosby's Lost Radio Performances | Shout! Factory | — | |
| 2004 | Have Yourself a Merry Little Christmass (Christmas collection) | Liquid 8 Records | — | |
| 2004 | Two Of A Kind (also featuring Bob Hope) | Universal Special Products | — | |
| 2005 | Bing Crosby Christmas Collection (Christmas collection) | Timeless Media Group | — | |
| 2005 | The Original Crooner | American Legends | — | |
| 2005 | America's Favorite Entertainer | American Legends | — | |
| 2005 | Christmas with Frank Sinatra & Bing Crosby (Christmas collection) | St. Clair Entertainment Group, Inc. | — | |
| 2006 | The Definitive Collection | Geffen Records | — | |
| 2006 | Christmas Classics (Christmas collection) | Capitol Records, UMe | — | BPI: Silver |
| 2006 | White Christmas (Christmas collection - also featuring Rosemary Clooney) | LaserLight Digital | — | |
| 2006 | White Christmas (Christmas collection - different from above collection) | LaserLight Digital | — | |
| 2006 | The Essentials | Fantastic Price Records | — | |
| 2006 | Caroling with The Crooners (Christmas collection - also featuring Frank Sinatra and Nat King Cole) | KRB Music Companies | — | |
| 2006 | Best Of Bing Crosby | Direct Source Special Products Inc. | — | |
| 2006 | The Centennial Anthology (also included a DVD) | Master Classics | — | |
| 2007 | Seasons Greetings from Frank Sinatra & Bing Crosby (Christmas collection) | EMI Music Special Markets | — | |
| 2007 | Hits Of Bing Crosby | NorthQuest | — | |
| 2007 | A Crosby Christmas (Christmas collection) | Varèse Sarabande | — | |
| 2007 | Christmas With Bing Crosby & Friends (Christmas collection) | Forever Gold | — | |
| 2008 | Gold | Geffen Records | — | |
| 2008 | Bing Crosby Christmas (Christmas collection) | Allegro Corporation | — | |
| 2009 | The Essentials | Stardust Records | — | |
| 2009 | Bing Crosby White Christmas (Christmas collection) | Lifestyles | — | |
| 2009 | The Bing Crosby CBS Radio Recordings 1954-56 (7-CD box set) | Mosaic Records | — | |
| 2010 | On the Sentimental Side (posthumous edition, recorded in 1962; Bing Crosby's latest studio album) | Collectors' Choice Music | — | |
| 2010 | Bing on Broadway | Collectors' Choice Music | — | |
| 2010 | So Rare: Treasures from the Crosby Archive | Collectors' Choice Music | — | |
| 2010 | Bing Sings the Sinatra Songbook | Collectors' Choice Music | — | |
| 2010 | The Crosby Christmas Sessions (Christmas collection) | Collectors' Choice Music | — | |
| 2010 | Bing Sings the Great American Songbook | Collectors' Choice Music | — | |
| 2010 | The Crosby-Clooney Radio Sessions | Collectors' Choice Music | — | |
| 2011 | Christmas Favorites (Christmas collection) | The Bing Crosby Archive | — | |
| 2011 | Icon | Geffen Records, UMe | — | |
| 2011 | Bing In Dixieland | Bing Crosby Enterprises | — | |
| 2011 | Christmas (Christmas collection) | Sonoma Entertainment | — | |
| 2011 | Christmas by the Fire (Christmas collection - came with a fireplace DVD) | Universal Music Special Markets | — | |
| 2012 | Christmas (10 Great Songs) (Christmas collection) | Capitol Records | — | |
| 2012 | Bing Crosby Christmas (Christmas collection) | Lifestyles | — | |
| 2012 | Through The Years: Volume Ten (with Paul Weston and His Orchestra, Norman Luboff Choir, Dick Haymes, & The Andrews Sisters) | Sepia Records | — | |
| 2013 | Christmas with Bing! (Christmas collection) | Sony Music Commercial Music Group, The Bing Crosby Archive | — | |
| 2013 | Bing Sings the Johnny Mercer Songbook | Bing Crosby Enterprises | — | |
| 2014 | Bing Sings the Irving Berlin Songbook | Bing Crosby Enterprises | — | |
| 2014 | American Masters: Bing Crosby Rediscovered - The Soundtrack | Bing Crosby Enterprises | — | |
| 2016 | The Twelve Days Of Christmas/Radio Broadcast (Christmas collection) | Sounds Of Yester Year | — | |
| 2017 | Among My Souvenirs: More Treasures from the Crosby Archive | UMe | — | |
| 2017 | Christmas (Christmas collection) | Newbourne Media, Universal Music Special Markets | — | |
| 2019 | Bing at Christmas (Christmas collection) | Decca | 9 (UK) | BPI: Silver |
| 2021 | The All-Time Best of Bing Crosby | Curb Records | — | |
| 2023 | A Valentine from Bing | Primary Wave Music (Worldwide) | — | |
| 2023 | Bing Crosby’s Irish Songbook | Primary Wave Music (Worldwide) | — | |
| 2023 | Bing & Ella (w/ Ella Fitzgerald) | Primary Wave Music | — | |
| 2023 | Bing Crosby's Christmas Gems (Christmas collection) | Primary Wave Music | — | |
| 2023 | Bing at the Movies (Volume 1) | Primary Wave Music (Worldwide) | — | |
| 2024 | Ultimate Christmas (Christmas collection) | UMG Recordings | 3 (US) | |

## Singles
### Pre-Decca era

| Year | Single | Chart positions | Chart positions | Chart positions | Chart positions | Chart positions |
| Year | Single | US | US R&B | US AC | US Country | UK |
| 1927 | "Muddy Water" (with Paul Whiteman) | 11 | — | — | — | — |
| 1927 | "Side by Side" (The Rhythm Boys with Paul Whiteman) | 3 | — | — | — | — |
| 1927 | "I'm Coming, Virginia" (The Rhythm Boys with Paul Whiteman) | 6 | — | — | — | — |
| 1927 | "My Blue Heaven" (with Paul Whiteman et al.) | 1 | — | — | — | — |
| 1927 | "The Calinda" (with Paul Whiteman et al.) | 7 | — | — | — | — |
| 1928 | "Changes" (with Paul Whiteman et al.) | 4 | — | — | — | — |
| 1928 | "Ol' Man River" (with Paul Whiteman) | 1 | — | — | — | — |
| 1928 | "Make Believe" (with Paul Whiteman) | 7 | — | — | — | — |
| 1928 | "Sunshine" (with Paul Whiteman et al.) | 6 | — | — | — | — |
| 1928 | "Mississippi Mud" (with Paul Whiteman et al.) | 6 | — | — | — | — |
| 1928 | "Mississippi Mud" (with Frankie Trumbauer) | 18 | — | — | — | — |
| 1928 | "From Monday On" (with Paul Whiteman et al.) | 14 | — | — | — | — |
| 1928 | "You Took Advantage of Me" (with Paul Whiteman et al.) | 9 | — | — | — | — |
| 1928 | "Louisiana" (with Paul Whiteman et al.) | 12 | — | — | — | — |
| 1928 | "It Was the Dawn of Love" (with Paul Whiteman et al.) | 19 | — | — | — | — |
| 1928 | "I'm on the Crest of a Wave" (with Paul Whiteman et al.) | 6 | — | — | — | — |
| 1928 | "Out-O'-Town Gal" (with Paul Whiteman et al.) | 16 | — | — | — | — |
| 1929 | "Makin' Whoopee" (with Paul Whiteman et al.) | 8 | — | — | — | — |
| 1929 | "Let's Do It" (with Dorsey Brothers) | 9 | — | — | — | — |
| 1929 | "Louise" (with Paul Whiteman) | 6 | — | — | — | — |
| 1929 | "Little Pal" (with Paul Whiteman) | 9 | — | — | — | — |
| 1929 | "Your Mother and Mine" (with Paul Whiteman et al.) | 16 | — | — | — | — |
| 1929 | "Waiting at the End of the Road" (with Paul Whiteman) | 12 | — | — | — | — |
| 1929 | "I'm A Dreamer, Aren't We All?" (with Paul Whiteman et al.) | 6 | — | — | — | — |
| 1929 | "If I Had a Talking Picture of You" (with Paul Whiteman) | 7 | — | — | — | — |
| 1929 | "Great Day" (with Paul Whiteman) | 1 | — | — | — | — |
| 1929 | "Without a Song" (with Paul Whiteman) | 6 | — | — | — | — |
| 1929 | "A Bundle of Old Love Letters" (with Paul Whiteman) | 10 | — | — | — | — |
| 1930 | "After You've Gone" (with Paul Whiteman) | 14 | — | — | — | — |
| 1930 | "I Like to Do Things for You" (with Paul Whiteman et al.) | 19 | — | — | — | — |
| 1930 | "You Brought a New Kind of Love to Me" (with Paul Whiteman) | 3 | — | — | — | — |
| 1930 | "Livin' in the Sunlight, Lovin' in the Moonlight" (with Paul Whiteman) | 16 | — | — | — | — |
| 1930 | "It Must Be True" (with Gus Arnheim) | 4 | — | — | — | — |
| 1930 | "Three Little Words" (with Duke Ellington et al.) | 1 | — | — | — | — |
| 1930 | "Them There Eyes" (with Gus Arnheim & The Rhythm Boys) | 7 | — | — | — | — |
| 1931 | "The Little Things in Life" (with Gus Arnheim) | 4 | — | — | — | — |
| 1931 | "I Surrender Dear" (with Gus Arnheim) | 3 | — | — | — | — |
| 1931 | "One More Time" (with Gus Arnheim) | 4 | — | — | — | — |
| 1931 | "Just a Gigolo" | 12 | — | — | — | — |
| 1931 | "Out of Nowhere" | 1 | — | — | — | — |
| 1931 | "Ho Hum!" (with Gus Arnheim & Loyce Whiteman) | 6 | — | — | — | — |
| 1931 | "Wrap Your Troubles in Dreams" | 4 | — | — | — | — |
| 1931 | "Just One More Chance" | 1 | — | — | — | — |
| 1931 | "Were You Sincere?" | 12 | — | — | — | — |
| 1931 | "I Found a Million Dollar Baby" | 2 | — | — | — | — |
| 1931 | "I'm Thru with Love" | 3 | — | — | — | — |
| 1931 | "At Your Command" | 1 | — | — | — | — |
| 1931 | "Many Happy Returns of the Day" | 3 | — | — | — | — |
| 1931 | "Stardust" | 5 | — | — | — | — |
| 1931 | "Dancing in the Dark" | 3 | — | — | — | — |
| 1931 | "I Apologize" | 3 | — | — | — | — |
| 1931 | "Sweet and Lovely" | 9 | — | — | — | — |
| 1931 | "Goodnight, Sweetheart" | 5 | — | — | — | — |
| 1931 | "A Faded Summer Love" | 8 | — | — | — | — |
| 1931 | "Gems from George White's Scandals" (with Mills Brothers, The Boswell Sisters & Victor Young) | 3 | — | — | — | — |
| 1932 | "Dinah" (with Mills Brothers) | 1 | — | — | — | — |
| 1932 | "Can't We Talk It Over?" (with Helen Crawford) | 10 | — | — | — | — |
| 1932 | "Where the Blue of the Night (Meets the Gold of the Day)" (Bing's Theme Song) | 4 | — | — | — | — |
| 1932 | "Snuggled on Your Shoulder (Cuddled in Your Arms)" | 11 | — | — | — | — |
| 1932 | "Paradise" | 7 | — | — | — | — |
| 1932 | "Shine" (with Mills Brothers) | 7 | — | — | — | — |
| 1932 | "Lazy Day" | 4 | — | — | — | — |
| 1932 | "Sweet Georgia Brown" | 2 | — | — | — | — |
| 1932 | "Cabin in the Cotton" | 11 | — | — | — | — |
| 1932 | "Love Me Tonight" | 4 | — | — | — | — |
| 1932 | "Some of These Days" | 16 | — | — | — | — |
| 1932 | "Please" | 1 | — | — | — | — |
| 1932 | "Waltzing in a Dream" | 6 | — | — | — | — |
| 1932 | "Here Lies Love" | 11 | — | — | — | — |
| 1932 | "Brother, Can You Spare a Dime?" | 1 | — | — | — | — |
| 1933 | "Just an Echo in the Valley" | 2 | — | — | — | — |
| 1933 | "I Don't Stand a Ghost of a Chance with You" | 5 | — | — | — | — |
| 1933 | "Street of Dreams" | 13 | — | — | — | — |
| 1933 | "You're Getting to Be a Habit with Me" | 1 | — | — | — | — |
| 1933 | "Young and Healthy" | 2 | — | — | — | — |
| 1933 | "You're Beautiful Tonight, My Dear" | 12 | — | — | — | — |
| 1933 | "I've Got the World on a String" | 19 | — | — | — | — |
| 1933 | "You've Got Me Crying Again" | 12 | — | — | — | — |
| 1933 | "Shadow Waltz" | 1 | — | — | — | — |
| 1933 | "I've Got to Sing a Torch Song" | 9 | — | — | — | — |
| 1933 | "Learn to Croon" | 3 | — | — | — | — |
| 1933 | "Down the Old Ox Road" | 8 | — | — | — | — |
| 1933 | "Blue Prelude" | 10 | — | — | — | — |
| 1933 | "My Love" | 4 | — | — | — | — |
| 1933 | "Thanks" | 2 | — | — | — | — |
| 1933 | "The Day You Came Along" | 3 | — | — | — | — |
| 1933 | "The Last Round-Up" | 2 | — | — | — | — |
| 1933 | "Home on the Range" | 18 | — | — | — | — |
| 1933 | "Beautiful Girl" | 11 | — | — | — | — |
| 1933 | "Temptation" | 3 | — | — | — | — |
| 1933 | "Did You Ever See a Dream Walking?" | 5 | — | — | — | — |
| 1934 | "We'll Make Hay While the Sun Shines" | 8 | — | — | — | — |
| 1934 | "Little Dutch Mill" | 1 | — | — | — | — |
| 1934 | "Good Night, Lovely Little Lady" | 2 | — | — | — | — |
| 1934 | "Once in a Blue Moon" | 11 | — | — | — | — |
| 1934 | "Love Thy Neighbor" | 2 | — | — | — | — |
| 1934 | "Ridin' Around in the Rain" | 13 | — | — | — | — |
| 1934 | "May I?" | 4 | — | — | — | — |
| 1934 | "She Reminds Me of You" | 10 | — | — | — | — |
| 1934 | "Love in Bloom" | 1 | — | — | — | — |
| 1934 | "Straight from the Shoulder" | 16 | — | — | — | — |
| 1934 | "Give Me a Heart to Sing To" | 12 | — | — | — | — |

### Decca and beyond

| Year | Single | Chart positions | Chart positions | Chart positions | Chart positions | Chart positions |
| Year | Single | US | US R&B | US AC | US Country | UK |
| 1934 | "Two Cigarettes in the Dark" | 5 | — | — | — | — |
| 1934 | "The Very Thought of You" | 11 | — | — | — | — |
| 1934 | "The Moon Was Yellow" | 13 | — | — | — | — |
| 1934 | "June in January" (from Crosbyana) | 1 | — | — | — | — |
| 1934 | "Love Is Just Around the Corner" (from Crosbyana) | 8 | — | — | — | — |
| 1934 | "With Every Breath I Take" (from Crosbyana) | 4 | — | — | — | — |
| 1934 | "Maybe I'm Wrong Again" | 14 | — | — | — | — |
| 1935 | "Soon" (from Crosbyana) | 1 | — | — | — | — |
| 1935 | "Down by the River" (from Crosbyana) | 17 | — | — | — | — |
| 1935 | "It's Easy to Remember" (from Crosbyana) | 1 | — | — | — | — |
| 1935 | "I Wished on the Moon" (from Crosbyana) | 2 | — | — | — | — |
| 1935 | "Without a Word of Warning" (from Crosbyana) | 5 | — | — | — | — |
| 1935 | "I Wish I Were Aladdin" (from Crosbyana) | 7 | — | — | — | — |
| 1935 | "From the Top of Your Head to the Tip of Your Toes" (from Crosbyana) | 10 | — | — | — | — |
| 1935 | "Red Sails in the Sunset" | 1 | — | — | — | — |
| 1935 | "Silent Night" (gold record) (from Christmas Music) | 7 | — | — | — | — |
| 1935 | "On Treasure Island" | 8 | — | — | — | — |
| 1936 | "Would You?" | 20 | — | — | — | — |
| 1936 | "The Touch of Your Lips" | 4 | — | — | — | — |
| 1936 | "Robins and Roses" | 2 | — | — | — | — |
| 1936 | "It Ain't Necessarily So" | 18 | — | — | — | — |
| 1936 | "I'm an Old Cowhand" (from Cowboy Songs) | 2 | — | — | — | — |
| 1936 | "I Can't Escape from You" | 7 | — | — | — | — |
| 1936 | "Empty Saddles" (from Under Western Skies) | 8 | — | — | — | — |
| 1936 | "Song of the Islands" (from Music of Hawaii) | 14 | — | — | — | — |
| 1936 | "South Sea Island Magic" (from Favorite Hawaiian Songs) | 3 | — | — | — | — |
| 1936 | "Me and the Moon" | 9 | — | — | — | — |
| 1936 | "Pennies from Heaven" | 1 | — | — | — | — |
| 1936 | "Let's Call a Heart a Heart" | 10 | — | — | — | — |
| 1936 | "So Do I" | 18 | — | — | — | — |
| 1937 | "One, Two, Button Your Shoe" | 19 | — | — | — | — |
| 1937 | "Sweet Leilani" (gold record) (from Favorite Hawaiian Songs) | 1 | — | — | — | — |
| 1937 | "Blue Hawaii" (from Favorite Hawaiian Songs) | 5 | — | — | — | — |
| 1937 | "Too Marvelous for Words" | 1 | — | — | — | — |
| 1937 | "What Will I Tell My Heart?" | 5 | — | — | — | — |
| 1937 | "Sweet Is the Word for You" | 8 | — | — | — | — |
| 1937 | "Never in a Million Years" | 2 | — | — | — | — |
| 1937 | "Moonlight and Shadows" | 10 | — | — | — | — |
| 1937 | "My Little Buckaroo" (from Cowboy Songs) | 19 | — | — | — | — |
| 1937 | "Peckin'" (w/ Jimmy Dorsey) | 9 | — | — | — | — |
| 1937 | "The Moon Got in My Eyes" | 1 | — | — | — | — |
| 1937 | "(You Know It All) Smarty" | 18 | — | — | — | — |
| 1937 | "It's the Natural Thing to Do" | 2 | — | — | — | — |
| 1937 | "Remember Me?" | 1 | — | — | — | — |
| 1937 | "I Still Love to Kiss You Goodnight" | 6 | — | — | — | — |
| 1937 | "Can I Forget You?" | 8 | — | — | — | — |
| 1937 | "Bob White (Whatcha Gonna Swing Tonight?)" (w/ Connee Boswell) | 1 | — | — | — | — |
| 1937 | "Basin Street Blues" (w/ Connee Boswell) | 12 | — | — | — | — |
| 1937 | "The One Rose (That's Left in My Heart)" | 8 | — | — | — | — |
| 1937 | "Sail Along, Silv'ry Moon" (from Favorite Hawaiian Songs) | 4 | — | — | — | — |
| 1938 | "When the Organ Played 'O, Promise Me'" | 5 | — | — | — | — |
| 1938 | "There's a Gold Mine in the Sky" (w/ Eddie Dunstedter) (from Cowboy Songs) | 6 | — | — | — | — |
| 1938 | "On the Sentimental Side" | 4 | — | — | — | — |
| 1938 | "The Moon of Manakoora" | 10 | — | — | — | — |
| 1938 | "Let Me Whisper I Love You" | 7 | — | — | — | — |
| 1938 | "When Mother Nature Sings Her Lullaby" | 3 | — | — | — | — |
| 1938 | "Now It Can Be Told" | 7 | — | — | — | — |
| 1938 | "I've Got a Pocketful of Dreams" | 1 | — | — | — | — |
| 1938 | "Small Fry" (w/ Johnny Mercer) (from Small Fry) | 3 | — | — | — | — |
| 1938 | "Mr. Gallagher & Mr. Shean" (w/ Johnny Mercer) (from Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer) | 7 | — | — | — | — |
| 1938 | "Alexander's Ragtime Band" (w/ Connee Boswell) | 1 | — | — | — | — |
| 1938 | "Don't Let That Moon Get Away" | 19 | — | — | — | — |
| 1938 | "Mexicali Rose" (from Cowboy Songs) | 3 | — | — | — | — |
| 1938 | "My Reverie" | 3 | — | — | — | — |
| 1938 | "You Must Have Been a Beautiful Baby" | 1 | — | — | — | — |
| 1939 | "You're a Sweet Little Headache" | 3 | — | — | — | — |
| 1939 | "I Have Eyes" | 4 | — | — | — | — |
| 1939 | "The Funny Old Hills" | 5 | — | — | — | — |
| 1939 | "Someone Stole Gabriel's Horn" (w/ The Dorsey Brothers) | 14 | — | — | — | — |
| 1939 | "It's a Lonely Trail" (from Cowboy Songs) | 17 | — | — | — | — |
| 1939 | "The Lonesome Road" (from Star Dust) | 12 | — | — | — | — |
| 1939 | "I Cried for You" (from Star Dust) | 13 | — | — | — | — |
| 1939 | "Between a Kiss and a Sigh" | 15 | — | — | — | — |
| 1939 | "My Melancholy Baby" (from Star Dust) | 14 | — | — | — | — |
| 1939 | "Ah! Sweet Mystery of Life" (from Victor Herbert Melodies, Vol. 1) | 12 | — | — | — | — |
| 1939 | "East Side of Heaven" | 6 | — | — | — | — |
| 1939 | "Sing a Song of Sunbeams" | 8 | — | — | — | — |
| 1939 | "Deep Purple" (from Star Dust) | 14 | — | — | — | — |
| 1939 | "God Bless America" (from Patriotic Songs for Children) | 17 | — | — | — | — |
| 1939 | "That Sly Old Gentleman (from Featherbed Lane)" (from Small Fry) | 10 | — | — | — | — |
| 1939 | "Little Sir Echo" (from Small Fry) | 3 | — | — | — | — |
| 1939 | "And the Angels Sing" | 10 | — | — | — | — |
| 1939 | "Alla en el rancho grande" | 6 | — | — | — | — |
| 1939 | "Whistling in the Wildwood" | 14 | — | — | — | — |
| 1939 | "An Apple for the Teacher" (w/ Connee Boswell) (from Small Fry) | 2 | — | — | — | — |
| 1939 | "Go Fly a Kite" | 10 | — | — | — | — |
| 1939 | "A Man and His Dream" | 4 | — | — | — | — |
| 1939 | "Start the Day Right" (w/ Connee Boswell) (from Bing and Connee) | 12 | — | — | — | — |
| 1939 | "What's New?" | 2 | — | — | — | — |
| 1939 | "Ciribiribin (They're So in Love)" (w/ The Andrews Sisters) (from Bing Crosby and The Andrews Sisters - EP) | 13 | — | — | — | — |
| 1939 | "Yodelin' Jive" (w/ The Andrews Sisters) (from Bing Crosby and The Andrews Sisters - EP) | 4 | — | — | — | — |
| 1939 | "My Isle of Golden Dreams" (from Favorite Hawaiian Songs) | 18 | — | — | — | — |
| 1940 | "Between 18th & 19th on Chestnut Street" (w/ Connee Boswell) (from Bing and Connee) | 12 | — | — | — | — |
| 1940 | "Sweet Potato Piper" | 11 | — | — | — | — |
| 1940 | "Just One More Chance" (re-recording) | 16 | — | — | — | — |
| 1940 | "I'm Too Romantic" (aka "Too Romantic") | 3 | — | — | — | — |
| 1940 | "The Singing Hills" (from Under Western Skies) | 3 | — | — | — | — |
| 1940 | "Tumbling Tumbleweeds" (from Under Western Skies) | 12 | — | — | — | — |
| 1940 | "April Played the Fiddle" | 10 | — | — | — | — |
| 1940 | "I Haven't Time to Be a Millionaire" | 13 | — | — | — | — |
| 1940 | "Meet the Sun Half-Way" | 15 | — | — | — | — |
| 1940 | "Sierra Sue" (from Under Western Skies) | 2 | — | — | — | — |
| 1940 | "Mister Meadowlark" (w/ Johnny Mercer) (from Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer) | 18 | — | — | — | — |
| 1940 | "Trade Winds" (from Hawaii Calls) | 2 | — | — | — | — |
| 1940 | "Can't Get Indiana Off My Mind" | 8 | — | — | — | — |
| 1940 | "That's for Me" | 9 | — | — | — | — |
| 1940 | "Only Forever" | 1 | — | — | — | — |
| 1940 | "When the Moon Comes Over Madison Square" | 27 | — | — | — | — |
| 1940 | "Where the Blue of the Night (Meets the Gold of the Day)" (re-recording) (from Drifting and Dreaming) | 27 | — | — | — | — |
| 1940 | "You Made Me Love You" | 25 | — | — | — | — |
| 1941 | "Please" (re-recording) | 24 | — | — | — | — |
| 1941 | "Along the Santa Fe Trail" (from Under Western Skies) | 4 | — | — | — | — |
| 1941 | "Lone Star Trail" (from Under Western Skies) | 23 | — | — | — | — |
| 1941 | "New San Antonio Rose" (from Don't Fence Me In) | 7 | — | — | — | — |
| 1941 | "It Makes No Difference Now" (from Don't Fence Me In) | 23 | — | — | — | — |
| 1941 | "Did Your Mother Come From Ireland?" (from St. Patrick's Day) | 22 | — | — | — | — |
| 1941 | "Dolores" | 2 | — | — | — | — |
| 1941 | "Paradise Isle" (from Favorite Hawaiian Songs, Vol. One) | 23 | — | — | — | — |
| 1941 | "You and I" | 5 | — | — | — | — |
| 1941 | "Brahms' Lullaby" | 20 | — | — | — | — |
| 1941 | "'Til Reveille" | 6 | — | — | — | — |
| 1941 | "Be Honest With Me" (from Don't Fence Me In) | 19 | — | — | — | — |
| 1941 | "You Are My Sunshine" (from Don't Fence Me In) | 19 | — | — | — | — |
| 1941 | "The Whistler's Mother-in-law" (w/ Muriel Lane) | 9 | — | — | — | — |
| 1941 | "The Waiter and the Porter and the Upstairs Maid" (w/ Mary Martin & Jack Teagarden) | 23 | — | — | — | — |
| 1941 | "Clementine" | 20 | — | — | — | — |
| 1941 | "Shepherd Serenade" | 4 | — | — | — | — |
| 1941 | "The Anniversary Waltz" | 24 | — | — | — | — |
| 1942 | "Deep in the Heart of Texas" | 3 | — | — | — | — |
| 1942 | "I Don't Want to Walk Without You" | 9 | — | — | — | — |
| 1942 | "Sing Me a Song of the Islands" (from Favorite Hawaiian Songs, Vol. Two) | 22 | — | — | — | — |
| 1942 | "Miss You" | 9 | — | — | — | — |
| 1942 | "The Lamplighter's Serenade" | 23 | — | — | — | — |
| 1942 | "When the White Azaleas Start Blooming" | 21 | — | — | — | — |
| 1942 | "Skylark" | 14 | — | — | — | — |
| 1942 | "The Bombardier Song" | 19 | — | — | — | — |
| 1942 | "Be Careful, It's My Heart" (from Song Hits from Holiday Inn) | 2 | — | — | — | — |
| 1942 | "White Christmas" (gold record) (from Song Hits from Holiday Inn) | 1 | 1 | 3 | — | 5 |
| 1942 | "Moonlight Becomes You" | 3 | — | — | — | — |
| 1943 | "Constantly" | 13 | — | — | — | — |
| 1943 | "Sunday, Monday, or Always" (gold record) | 1 | 3 | — | — | — |
| 1943 | "If You Please" | 17 | — | — | — | — |
| 1943 | "Mary's a Grand Old Name" | 20 | — | — | — | — |
| 1943 | "People Will Say We're in Love" (from Bing Crosby Sings the Song Hits from Broadway Shows) | 2 | — | — | — | — |
| 1943 | "Oh, What a Beautiful Mornin'" (from Bing Crosby Sings the Song Hits from Broadway Shows) | 4 | — | — | — | — |
| 1943 | "Pistol Packin' Mama" (w/ The Andrews Sisters) (gold record) (from Don't Fence Me In) | 2 | 3 | — | 1 | — |
| 1943 | "Vict'ry Polka" (w/ The Andrews Sisters) | 5 | — | — | — | — |
| 1943 | "I'll Be Home for Christmas (If Only in My Dreams)" (gold record) (from Merry Christmas) | 3 | 8 | — | — | — |
| 1943 | "White Christmas" (gold record) | 6 | — | — | — | — |
| 1943 | "Jingle Bells" (w/ The Andrews Sisters) (from Merry Christmas) | 19 | — | — | — | — |
| 1943 | "Let's Start the New Year Right" (from Song Hits from Holiday Inn) | 18 | — | — | — | — |
| 1944 | "San Fernando Valley" | 1 | — | — | — | — |
| 1944 | "Poinciana" | 3 | — | — | — | — |
| 1944 | "I Love You" | 1 | — | — | — | — |
| 1944 | "I'll Be Seeing You" | 1 | — | — | — | — |
| 1944 | "Swinging on a Star" (gold record) (from Selections from Going My Way) | 1 | — | — | — | — |
| 1944 | "Going My Way" (from Selections from Going My Way) | 15 | — | — | — | — |
| 1944 | "Is You Is or Is You Ain't My Baby" (w/ The Andrews Sisters) | 2 | — | — | — | — |
| 1944 | "Amor" | 2 | — | — | — | — |
| 1944 | "Long Ago (and Far Away)" | 5 | — | — | — | — |
| 1944 | "The Day After Forever" | 15 | — | — | — | — |
| 1944 | "Hot Time in the Town of Berlin" (w/ The Andrews Sisters) | 1 | — | — | — | — |
| 1944 | "It Could Happen to You" | 18 | — | — | — | — |
| 1944 | "Too-Ra-Loo-Ra-Loo-Ral" (gold record) (from Selections from Going My Way) | 4 | — | — | — | — |
| 1944 | "White Christmas" (gold record) | 5 | — | — | — | — |
| 1944 | "Don't Fence Me In" (w/ The Andrews Sisters) (gold record) (from Don't Fence Me In) | 1 | 9 | — | — | — |
| 1945 | "Evelina" (from Bing Crosby Sings the Song Hits from Broadway Shows) | 9 | — | — | — | — |
| 1945 | "Ac-Cent-Tchu-Ate the Positive" (w/ The Andrews Sisters) | 2 | — | — | — | — |
| 1945 | "The Three Caballeros" (w/ The Andrews Sisters) | 8 | — | — | — | — |
| 1945 | "Sleigh Ride in July" | 14 | — | — | — | — |
| 1945 | "Like Someone in Love" | 15 | — | — | — | — |
| 1945 | "Just a Prayer Away" | 4 | — | — | — | — |
| 1945 | "All of My Life" | 12 | — | — | — | — |
| 1945 | "Yah-ta-ta, Yah-ta-ta (Talk, Talk, Talk)" (w/ Judy Garland) (from Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer) | 5 | — | — | — | — |
| 1945 | "You Belong to My Heart" (from El Bingo – A Collection of Latin American Favorites) | 3 | — | — | — | — |
| 1945 | "Baia" (from El Bingo – A Collection of Latin American Favorites) | 6 | — | — | — | — |
| 1945 | "My Baby Said Yes" (w/ Louis Jordan) | 14 | — | — | — | — |
| 1945 | "On the Atchison, Topeka and the Santa Fe" | 3 | — | — | — | — |
| 1945 | "If I Loved You" (from Bing Crosby Sings the Song Hits from Broadway Shows) | 8 | — | — | — | — |
| 1945 | "Along the Navajo Trail" (w/ The Andrews Sisters) (from Go West Young Man) | 2 | — | — | — | — |
| 1945 | "It's Been a Long, Long Time" (w/ Les Paul Trio) (from Drifting and Dreaming) | 1 | — | — | — | — |
| 1945 | "The Road to Morocco" (w/ Bob Hope) (from Selections from Road to Utopia) | 21 | — | — | — | — |
| 1945 | "I Can't Begin to Tell You" (gold record) | 1 | — | — | — | — |
| 1945 | "White Christmas" (gold record) | 1 | — | — | — | — |
| 1945 | "Aren't You Glad You're You?" (from Selections from The Bells of St. Mary's) | 8 | — | — | — | — |
| 1945 | "In the Land of Beginning Again" (from Selections from The Bells of St. Mary's) | 18 | — | — | — | — |
| 1945 | "Symphony" | 3 | — | — | — | — |
| 1946 | "Give Me the Simple Life" | 16 | — | — | — | — |
| 1946 | "The Bells of St. Mary's" (from Selections from The Bells of St. Mary's) | 21 | — | — | — | — |
| 1946 | "McNamara's Band" (gold record) (from St. Patrick's Day) | 10 | — | — | — | — |
| 1946 | "Day by Day" (w/ Mel Tormé & His Mel-Tones) | 15 | — | — | — | — |
| 1946 | "Sioux City Sue" | 3 | — | — | — | — |
| 1946 | "Personality" (from Selections from Road to Utopia) | 9 | — | — | — | — |
| 1946 | "They Say It's Wonderful" (from Bing Crosby Sings the Song Hits from Broadway Shows) | 12 | — | — | — | — |
| 1946 | "South America, Take It Away" (w/ The Andrews Sisters) (gold record) | 2 | — | — | — | — |
| 1946 | "(Get Your Kicks on) Route 66" (w/ The Andrews Sisters) | 14 | — | — | — | — |
| 1946 | "Night and Day" | 21 | — | — | — | — |
| 1946 | "You Keep Coming Back Like a Song" (from Blue Skies) | 12 | — | — | — | — |
| 1946 | "White Christmas" (gold record) | 1 | — | — | — | — |
| 1947 | "A Gal in Calico" | 8 | — | — | — | — |
| 1947 | "Easter Parade" (from Song Hits from Holiday Inn) | 22 | — | — | — | — |
| 1947 | "That's How Much I Love You" | 17 | — | — | — | — |
| 1947 | "Alexander's Ragtime Band" (w/ Al Jolson) (gold record) (from Bing Crosby Sings with Al Jolson, Bob Hope, Dick Haymes and the Andrews Sisters) | 20 | — | — | — | — |
| 1947 | "Tallahassee" (w/ The Andrews Sisters) | 10 | — | — | — | — |
| 1947 | "There's No Business Like Show Business" (w/ The Andrews Sisters & Dick Haymes) (from Bing Crosby Sings with Al Jolson, Bob Hope, Dick Haymes and the Andrews Sisters) | 25 | — | — | — | — |
| 1947 | "Feudin' and Fightin'" (from Bing and the Dixieland Bands) | 9 | — | — | — | — |
| 1947 | "The Freedom Train" (w/ The Andrews Sisters) | 21 | — | — | — | — |
| 1947 | "You Do" | 8 | — | — | — | — |
| 1947 | "How Soon (Will I Be Seeing You)" | 6 | — | — | — | — |
| 1947 | "The Whiffenpoof Song" (gold record) (from Auld Lang Syne) | 7 | — | — | — | — |
| 1947 | "White Christmas" (gold record) | 3 | — | — | — | — |
| 1947 | "Santa Claus Is Comin' to Town" (w/ The Andrews Sisters) | 22 | — | — | — | — |
| 1947 | "Silent Night" (new version) | 22 | — | — | — | 8 |
| 1948 | "Ballerina" | 10 | — | — | — | — |
| 1948 | "Now Is the Hour" (gold record) (from Auld Lang Syne) | 1 | — | — | — | — |
| 1948 | "You Don't Have to Know the Language" (w/ The Andrews Sisters) (from Selections from Road to Rio) | 21 | — | — | — | — |
| 1948 | "Pass That Peace Pipe" | 21 | — | — | — | — |
| 1948 | "But Beautiful" (from Selections from Road to Rio) | 20 | — | — | — | — |
| 1948 | "Blue Shadows on the Trail" (from Home on the Range) | 23 | — | — | — | — |
| 1948 | "A Fella with an Umbrella" | 23 | — | — | — | — |
| 1948 | "White Christmas" (gold record) | 6 | — | — | — | — |
| 1948 | "A Hundred and Sixty Acres" (w/ The Andrews Sisters) (from Go West Young Man) | 23 | — | — | — | — |
| 1949 | "Far Away Places" | 2 | — | — | — | — |
| 1949 | "Galway Bay" (gold record) (from When Irish Eyes Are Smiling) | 3 | — | — | — | — |
| 1949 | "If You Stub Your Toe on the Moon" (from A Connecticut Yankee in King Arthur's Court) | 27 | — | — | — | — |
| 1949 | "Careless Hands" | 12 | — | — | — | — |
| 1949 | "Riders in the Sky" | 14 | — | — | — | — |
| 1949 | "Some Enchanted Evening" (from South Pacific) | 3 | — | — | — | — |
| 1949 | "Bali Ha'i" (from South Pacific) | 12 | — | — | — | — |
| 1949 | "Dear Hearts and Gentle People" (gold record) | 2 | — | — | — | — |
| 1949 | "Mule Train" | 4 | — | — | — | — |
| 1949 | "Way Back Home" (from Way Back Home) | 21 | — | — | — | — |
| 1949 | "White Christmas" (gold record) | 5 | — | — | — | — |
| 1950 | "Have I Told You Lately That I Love You?" (w/ The Andrews Sisters) (from Go West Young Man) | 24 | — | — | — | — |
| 1950 | "Quicksilver" (w/ The Andrews Sisters) (from Go West Young Man) | 6 | — | — | — | — |
| 1950 | "Chattanoogie Shoe Shine Boy" | 4 | — | — | — | — |
| 1950 | "I Didn't Slip, I Wasn't Pushed, I Fell" | 22 | — | — | — | — |
| 1950 | "Play a Simple Melody" (w/ Gary Crosby) (gold record) (from Gary Crosby and Friend - EP) | 4 | — | — | — | — |
| 1950 | "Sam's Song" (w/ Gary Crosby) (from Gary Crosby and Friend - EP) | 4 | — | — | — | — |
| 1950 | "La Vie en rose" | 13 | — | — | — | — |
| 1950 | "I Cross My Fingers" | 18 | — | — | — | — |
| 1950 | "All My Love" | 11 | — | — | — | — |
| 1950 | "Beyond the Reef" | 26 | — | — | — | — |
| 1950 | "Harbor Lights" | 8 | — | — | — | — |
| 1950 | "White Christmas" (gold record) | 13 | — | — | — | — |
| 1950 | "Rudolph the Red-Nosed Reindeer" | 14 | — | — | — | — |
| 1950 | "A Crosby Christmas" (w/ his sons) | 22 | — | — | — | — |
| 1951 | "A Marshmallow World" | 14 | — | — | — | — |
| 1951 | "Sparrow in the Treetop" (w/ The Andrews Sisters) | 8 | — | — | — | — |
| 1951 | "When You and I Were Young, Maggie Blues" (w/ Gary Crosby) (from Gary Crosby and Friend - EP) | 8 | — | — | — | — |
| 1951 | "Moonlight Bay" (w/ Gary Crosby) (from Gary Crosby and Friend - EP) | 14 | — | — | — | — |
| 1951 | "Gone Fishin'" (w/ Louis Armstrong) | 19 | — | — | — | — |
| 1951 | "In the Cool, Cool, Cool of the Evening" (w/ Jane Wyman) | 11 | — | — | — | — |
| 1951 | "Shanghai" | 21 | — | — | — | — |
| 1951 | "Domino" | 15 | — | — | — | — |
| 1951 | "White Christmas" (gold record) | 13 | — | — | — | — |
| 1952 | "The Isle of Innisfree" (from Themes and Songs from The Quiet Man) | — | — | — | — | 3 |
| 1952 | "Watermelon Weather" (w/ Peggy Lee) | 28 | — | — | — | — |
| 1952 | "Till the End of the World" | 16 | — | — | 10 | — |
| 1952 | "Zing a Little Zong" (w/ Jane Wyman) (from Selections from the Paramount Picture "Just for You") | 18 | — | — | — | 10 |
| 1952 | "Silver Bells" (w/ Carol Richards) | 20 | — | — | — | — |
| 1952 | "Keep It a Secret" | 28 | — | — | — | — |
| 1953 | "You Don't Know What Lonesome Is" (from Home on the Range) | 23 | — | — | — | — |
| 1953 | "Open Up Your Heart" | 22 | — | — | — | — |
| 1953 | "Hush-a-bye" | 24 | — | — | — | — |
| 1953 | "White Christmas" (gold record) | 21 | — | — | — | — |
| 1954 | "Changing Partners" (from Bing Sings the Hits) | 13 | — | — | — | 9 |
| 1954 | "Y'all Come" (from Bing Sings the Hits) | 20 | — | — | — | — |
| 1954 | "Down by the Riverside" (w/ Gary Crosby) | 28 | — | — | — | — |
| 1954 | "Young at Heart" | 24 | — | — | — | — |
| 1954 | "Count Your Blessings Instead of Sheep" (from Selections from Irving Berlin's White Christmas) | 27 | — | — | — | 11 |
| 1954 | "White Christmas" (gold record) (from Selections from Irving Berlin's White Christmas) | 21 | — | — | — | — |
| 1955 | "Stranger in Paradise" (from Bing Sings the Hits) | — | — | — | — | 17 |
| 1955 | "White Christmas" (gold record) | 7 | — | — | — | — |
| 1956 | "In a Little Spanish Town" (w/ Buddy Cole & his Trio) (from In a Little Spanish Town) | 49 | — | — | — | 22 |
| 1956 | "True Love" (w/ Grace Kelly) (from High Society) | 3 | — | — | — | 4 |
| 1956 | "Well, Did You Evah!" (w/ Frank Sinatra) (from High Society) | 92 | — | — | — | — |
| 1956 | "Now You Has Jazz" (w/ Louis Armstrong) (from High Society) | 88 | — | — | — | — |
| 1956 | "White Christmas" (gold record) | 65 | — | — | — | — |
| 1957 | "Around the World" (from Around the World with Bing!) | 25 | — | — | — | 5 |
| 1957 | "How Lovely Is Christmas" (from A Christmas Story – An Axe, an Apple and a Buckskin Jacket) | 97 | — | — | — | — |
| 1957 | "Silent Night" | 54 | — | — | — | — |
| 1957 | "Silver Bells" (w/ Carol Richards) | 78 | — | — | — | — |
| 1957 | "White Christmas" (gold record) | 34 | — | — | — | — |
| 1958 | "White Christmas" (gold record) | 66 | — | — | — | — |
| 1959 | "White Christmas" (gold record) | 59 | — | — | — | — |
| 1960 | "Adeste Fideles" | 45 | — | — | — | — |
| 1960 | "I'll Be Home for Christmas (If Only in My Dreams)" (gold record) | 102 | — | — | — | — |
| 1960 | "Silent Night" | 54 | — | — | — | — |
| 1960 | "White Christmas" (gold record) | 26 | — | — | — | — |
| 1961 | "White Christmas" (gold record) | 12 | — | — | — | — |
| 1962 | "White Christmas" (gold record) | 38 | — | — | — | — |
| 1968 | "Step to the Rear" | — | — | 29 | — | — |
| 1975 | "That's What Life Is All About" (from That's What Life Is All About) | — | — | 35 | — | 41 |
| 1977 | "White Christmas" | — | — | — | — | 5 |
| 1982 | "Peace on Earth/Little Drummer Boy" (w/ David Bowie) | — | — | — | — | 3 |
| 1983 | "True Love" (w/ Grace Kelly) | — | — | — | — | 70 |
| 1985 | "White Christmas" | — | — | — | — | 69 |
| 1998 | "White Christmas" | — | — | — | — | 29 |
| 2018 | "White Christmas" | 34 | — | — | — | 61 |
| 2019 | "White Christmas" | 42 | — | — | — | 31 |
| 2020 | "White Christmas" | 20 | — | — | — | 49 |
| 2020 | "Mele Kalikimaka (Merry Christmas)" (w/ The Andrews Sisters) | 36 | — | — | — | — |
| 2020 | "I'll Be Home for Christmas (If Only in My Dreams)" | 50 | — | — | — | — |
| 2021 | "White Christmas" | 21 | — | — | — | 48 |
| 2022 | "White Christmas" | 16 | — | — | — | 39 |
| 2023 | "White Christmas" | 14 | — | — | — | 38 |
| 2024 | "White Christmas" | 19 | — | — | — | 42 |
| "Mele Kalikimaka (Merry Christmas)" (w/ The Andrews Sisters) | — | — | — | — | 71 |

### Holiday 100 chart entries

Since many radio stations in the US adopt a format change to Christmas music each December, many holiday hits have an annual spike in popularity during the last few weeks of the year and are retired once the season is over. In December 2011, Billboard began a Holiday Songs chart with 50 positions that monitors the last five weeks of each year to "rank the top holiday hits of all eras using the same methodology as the Hot 100, blending streaming, airplay, and sales data", and in 2013 the number of positions on the chart was doubled, resulting in the Holiday 100. Many Crosby recordings have made appearances on the Holiday 100 and are noted below according to the holiday season in which they charted there.
| Title | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Holiday season peak chart positions | Album |
| Title | 2011 | 2012 | 2013 | 2014 | 2015 | 2016 | 2017 | 2018 | 2019 | 2020 | 2021 | 2022 | 2023 | 2024 | Album |
| "Adeste Fideles (O Come, All Ye Faithful)" | — | — | — | — | 21 | — | — | — | — | — | — | — | — | — | Merry Christmas |
| "Do You Hear What I Hear?" | — | — | 79 | 70 | 38 | 90 | 67 | 70 | 74 | 82 | 70 | 95 | 87 | 76 | I Wish You a Merry Christmas |
| "Frosty the Snowman" | — | — | — | — | — | — | — | — | — | — | — | 94 | 89 | — | I Wish You a Merry Christmas |
| "I Wish You a Merry Christmas" | — | — | — | — | 49 | 86 | — | — | — | — | — | 93 | 92 | — | I Wish You a Merry Christmas |
| "I'll Be Home for Christmas" | — | — | — | — | — | — | 97 | 28 | 37 | 33 | 75 | 82 | 67 | 45 | Merry Christmas |
| "It's Beginning to Look a Lot Like Christmas" (with Jud Conlon's Rhythmaires) | 18 | 18 | 30 | 25 | 24 | 22 | 26 | 27 | 31 | 43 | 57 | 47 | 65 | 75 | Merry Christmas |
| "Let It Snow! Let It Snow! Let It Snow!" | — | — | — | — | — | — | — | — | 87 | — | — | — | — | — | I Wish You a Merry Christmas |
| "The Little Drummer Boy" | — | — | — | — | — | — | — | 46 | 46 | 62 | 81 | 79 | 90 | 89 | I Wish You a Merry Christmas |
| "Mele Kalikimaka (Merry Christmas)" (with The Andrews Sisters) | — | — | — | 61 | 87 | 74 | 87 | 73 | 36 | 25 | 56 | 42 | 44 | 39 | Merry Christmas |
| "Peace on Earth/Little Drummer Boy" (with David Bowie) | — | — | 87 | — | — | — | — | — | — | — | — | — | — | — | (non-album single) |
| "Santa Claus Is Coming to Town" (with The Andrews Sisters) | — | — | — | — | — | — | — | 90 | 61 | — | — | — | — | — | Merry Christmas |
| "Silent Night" | — | — | — | — | — | — | — | — | 88 | — | 73 | 76 | 64 | — | Merry Christmas |
| "Silver Bells" (with Carol Richards) | — | — | 95 | — | — | — | 63 | — | — | — | — | — | — | — | Merry Christmas |
| "White Christmas" | 11 | 7 | 7 | 8 | 5 | 12 | 10 | 11 | 16 | 13 | 13 | 13 | 13 | 17 | Merry Christmas |
| "Winter Wonderland" | — | — | — | — | — | — | — | 98 | 94 | 86 | — | 66 | 74 | 73 | I Wish You a Merry Christmas |