# John Michael Montgomery

John Michael Montgomery (born January 20, 1965) is an American country music singer. Active from 1992 to 2025, he has had more than 30 singles on the Billboard country charts. This total includes seven number-one singles: "I Love the Way You Love Me", "I Swear", "Be My Baby Tonight", "If You've Got Love", "I Can Love You Like That", "Sold (The Grundy County Auction Incident)", and "The Little Girl". Several of Montgomery's singles crossed over to the Billboard Hot 100, his highest peak there having been achieved by "Letters from Home" in 2004. "I Swear" and "I Can Love You Like That" were both covered by All-4-One, while "I Love the Way You Love Me" was covered by Boyzone.
Montgomery has released ten studio albums. His first seven were released via Atlantic Records Nashville, and his next two via parent company Warner Records Nashville after Atlantic closed its country division in 2001. After exiting that label, he released one album for his own Stringtown label in 2008. His first three albums, Life's a Dance (1992), Kickin' It Up (1994), and John Michael Montgomery (1995) are all certified multi-platinum by the Recording Industry Association of America (RIAA); 1996's What I Do the Best is certified platinum; while Leave a Mark (1998) and Brand New Me (2000) are certified gold. Montgomery's musical style includes a mix of ballads and up-tempo country rock material, and he has seen mixed to positive critical reception. Many critics have compared his musical image to that of Garth Brooks. Montgomery's brother, Eddie Montgomery, founded the duo Montgomery Gentry in the late 1990s; his nephew Dillon Carmichael and son-in-law Travis Denning are also country music singers.

## Early life

John Michael Montgomery was born January 20, 1965, in Danville, Kentucky, as the second of three children to Harold and Carol Montgomery. The family grew up in Nicholasville. Harold was a local musician who played at various honky-tonks throughout Kentucky and taught his son how to play guitar at an early age. By the time Montgomery was 15 years old, he began playing rhythm guitar in his family's band, Harold Montgomery and the Kentucky River Express, which his brother Eddie later joined as well. During his senior year of high school, Montgomery stocked frozen food at a local grocery store and lived with his grandmother after her husband died. These circumstances led to Montgomery missing over 70 days of school before deciding to drop out and complete his education through General Educational Development (GED).
Following their parents' divorce, Eddie and John Michael founded another group called Early Tymz, also known as John Michael Montgomery and Young Country. At the time, the brothers lived in an apartment together; John Michael worked at a liquor store and began dating a hair stylist named Kelly Welch. He became engaged to her in 1988, but he reneged as he wanted to focus on music. Additionally, he had his truck repossessed after missing loan payments; as Welch's grandmother co-signed the loan, Welch sued Montgomery for $5,000 before settling out of court. Montgomery continued to perform at local venues. In 1990, talent manager Estill Sowards discovered Montgomery performing at the Congress Inn, a bar in Lexington, Kentucky. Sowards came in contact with representatives of Atlantic Records, who also attended the Congress Inn to hear his performances. He signed to Atlantic Records's Nashville division in 1991, and he spent the next year selecting and recording songs.

## Musical career
### 1992–1993: Life's a Dance

Montgomery began recording his debut album after signing with Atlantic. The label originally selected songwriter and guitarist Wyatt Easterling as producer, but Montgomery was unsatisfied with the songs and production style Easterling had selected for him. As a result, he called Rick Blackburn (then-vice president of Atlantic Records's Nashville division) in the middle of the night to demand a different producer. Although Montgomery feared his actions would be negatively received, Blackburn ultimately recommended producer Doug Johnson. Blackburn allowed Montgomery to discard six songs recorded with Easterling in favor of ones selected by him and Johnson. Contributing musicians included guitarist Brent Rowan, bassist Willie Weeks, and drummer Owen Hale. Atlantic released "Life's a Dance" (written by Steve Seskin and Allen Shamblin) as the lead single, and shipped it to radio in September 1992. The song peaked at number four on the Billboard Hot Country Songs charts after release. It was included on his debut album, also titled Life's a Dance, released in 1993. The album's second single was "I Love the Way You Love Me". Written by Chuck Cannon and Victoria Shaw, the song became Montgomery's first number-one single on Hot Country Songs in 1993. It also went to number 60 on the Billboard Hot 100. In 1998, Irish group Boyzone released a cover version of "I Love the Way You Love Me". Released last off the project was "Beer and Bones", which was less successful on the country music charts with a peak of number 21. All three of the album's singles were among the tracks produced by Johnson.
Life's a Dance was met with mixed critical reception. Brian Mansfield reviewed the album favorably for AllMusic, praising Montgomery's baritone singing voice and the Western swing influence on certain tracks. The Spokesman-Review writer Debbie Fichtenberg Lind rated the album "B". Her review was also favorable toward Montgomery's singing voice and the lyrics of the first two singles, but was more critical toward the lyrics of "Beer and Bones" and "Dream On Texas Ladies". Billy Altman of Entertainment Weekly was less favorable, considering both the lyrics of "Life's a Dance" and Montgomery's overall musical image derivative of Garth Brooks, and rating the album "D". In 1995, Life's a Dance achieved a triple-platinum certification from the Recording Industry Association of America (RIAA), honoring shipments of three million copies. Montgomery was nominated for a Horizon Award (now known as Best New Artist) from the Country Music Association (CMA) in both 1993 and 1994, and won the award in the latter year. At the 1993 Academy of Country Music (ACM) Awards, Montgomery won Top New Male Vocalist, while "I Love the Way You Love Me" won Song of the Year.

### 1994–1995: Kickin' It Up

Montgomery's second Atlantic album was 1994's Kickin' It Up. It was led off by the single "I Swear", written by Gary Baker and Frank J. Myers. The song became Montgomery's second number-one single on the country charts, as well as his longest-tenured at four weeks. Additionally, it achieved a number 42 entry on the Hot 100. Soon after Montgomery's rendition, contemporary R&B group All-4-One released a cover version, which went on to become a number-one single on the Hot 100. The album itself peaked at number one on both Top Country Albums and the Billboard 200, accounting for his only number-one entry on the latter. Its next single was "Rope the Moon", which peaked at number four on the country charts; during this song's chart run, the album cut "Kick It Up" also charted for two weeks from unsolicited airplay. After these songs, both "Be My Baby Tonight" and "If You've Got Love" topped the country charts in 1994. Richard Fagan and Ed Hill wrote the former, while Seskin and Mark D. Sanders wrote the latter.
Scott Hendricks produced the album, with musical contributors including guitarists Dann Huff and Brent Mason; vocalists John Wesley Ryles and Harry Stinson; pianists Reese Wynans and John Barlow Jarvis; drummer Lonnie Wilson; and bassist Glenn Worf. Of the album's sound, Montgomery stated that he wanted it to be "rowdier" than his debut, which he felt lacked upbeat material outside "Beer and Bones". Writing for AllMusic, Michael McCall thought the album benefited from having more upbeat material than its predecessor, although he also noted that it still had "contemporary ballads" such as "I Swear". Mansfield similarly opined in a review for New Country magazine that the album was more energetic than his debut, citing "Be My Baby Tonight" and "Friday at Five" as examples. "I Swear" won both Single of the Year and Song of the Year from the Academy of Country Music, and Single of the Year from the Country Music Association. It also accounted for his first nomination from the Grammy Awards, in the category of Best Male Country Vocal Performance. Kickin' It Up was certified quadruple-platinum in 1996. Throughout 1994, Montgomery toured as an opening act for Reba McEntire. Due to the commercial success of Kickin' It Up, Montgomery was offered multiple opportunities to perform as a headlining act, but he declined as he thought he "was definitely not in the mental state" to do so.

### 1995–1996: John Michael Montgomery

In 1995, Montgomery released his third, self-titled studio album. It was led off by the ballad "I Can Love You Like That", which went to number one on the country music charts early in the year. Like "I Swear" before it, "I Can Love You Like That" was also covered by All-4-One, whose version was a top-five hit on the Hot 100. The album's second single, "Sold (The Grundy County Auction Incident)" (co-written by Fagan and former Bread member Robb Royer), became Montgomery's sixth number-one on Hot Country Songs in mid-1995. Three more singles reached top five on the country charts between then and early 1996: "No Man's Land" (also co-written by Seskin), "Cowboy Love", and "Long as I Live". Another track from the album, "Holdin' Onto Something", was also recorded by Jeff Carson, whose version was a top-ten country hit in 1996. Stephen Thomas Erlewine wrote in AllMusic, "the record doesn't sound dull or repetitive. Most of the album's success is due to the clean, commercial production, which makes even the weak material entertaining." Mansfield, in a review for New Country, thought the album "contains nearly everything that's predictable about modern country", although he also praised the Southern rock influence of "It's What I Am" and the lyrics of "No Man's Land". John Michael Montgomery, like its predcessor, was certified quadruple-platinum. The Country Music Association nominated it for Album of the Year, and Montgomery himself for Male Vocalist of the Year, while the music video for "Sold" received a Video of the Year nomination form the Academy of Country Music. Additionally, the Grammy Awards nominated John Michael Montgomery for Best Country Album, and "I Can Love You Like That" for Best Male Country Vocal Performance, with these representing his last nominations from that academy.
Despite his prior apprehensions about doing so, Montgomery began touring as a headliner in 1995 to promote his self-titled album. During these tours, he noticed he had begun to experience inconsistencies with his vocal tone in concert. Montgomery observed that he had begun experiencing occasional difficulties singing live in 1993, but that the problem had exacerbated by 1995. Consultants at Vanderbilt University Medical Center encouraged him to undergo rehabilitation. He initially refused, but later changed his mind after experiencing a persistent sore throat and difficulty speaking. A second consultation at Vanderbilt University Medical Center revealed that he had an infected salivary gland, which was surgically removed. Montgomery performed "Sold" at the annual Country Music Association awards telecast in November 1995, two weeks after his surgery.

### 1996–1997: What I Do the Best and Greatest Hits

Montgomery took another hiatus from touring in 1996, which resulted in him not performing any concerts at all that year. He later attributed this hiatus to a bout of depression he felt after the death of his father in 1994, followed by his marriage and the birth of his daughter in 1996. Despite his lack of touring, he released his fourth studio album What I Do the Best that year. For this album, Csaba Petocz served as producer. Nick Krewen of the Waterloo Region Record thought that the change in producers was due to Hendricks taking on an executive role at the Nashville branch of Capitol Records. "Ain't Got Nothin' on Us" served as the lead single. Montgomery said that he and Blackburn chose the song as a lead single due to it being an up-tempo Western swing song, compared to the ballads that had served as lead singles to previous albums. However, a station in Texas began playing the track "Friends" shortly after the album's release, causing the latter to enter the country music charts. In response, Atlantic withdrew "Ain't Got Nothin' on Us" in favor of "Friends", thus making it the project's second single. "Ain't Got Nothin' on Us" fell from a peak of number fifteen on Hot Country Songs, while "Friends" ascended to a peak of number two on that chart by year's end, in addition to reaching number 69 on the Hot 100.
"I Miss You a Little" was the album's third single, and Montgomery's first songwriting credit. He co-wrote the song as a tribute to his father, Harold, who died in 1994. Its music video featured pictures of Harold and his tombstone, as well as an audio recording of him. Barbara Montgomery (John Michael's stepmother and Harold's widow) filed a lawsuit against him after the music video's release, claiming that the singer had not gotten permission from her to use his likeness. By October 1998, John Michael won the lawsuit. Both "I Miss You a Little" and its follow-up, "How Was I to Know", were top-ten country hits in 1997. During this album's promotion, Montgomery also provided vocals to "Warning Signs", a comedy routine by Bill Engvall set to music, which charted for five weeks while "How Was I to Know" was also ascending the charts. An uncredited review in Billboard considered What I Do the Best to be Montgomery's "strongest yet", highlighting the lyrics of "I Miss You a Little" as well as the "traditional" sound of Petocz's production. Krewen was less favorable toward the album, as the thought the songs were inferior to those of previous albums and that Petocz's production did not fit with Montgomery's singing voice. The RIAA awarded What I Do the Best a platinum certification.
When Montgomery returned to touring in 1997, he reduced his number of shows per year from 150 to 50 as he felt he should "settle down". Also in 1997, Montgomery released his Greatest Hits package. Included on it was one new song, "Angel in My Eyes", which was also a top-five hit upon release to country radio that year. Writing for Country Standard Time, Walter Allread criticized Montgomery's "overly forceful" delivery of this song, and panned the album's packaging for resembling advertisements for blue jeans.

### 1998–2001: Leave a Mark, Home to You, and Brand New Me

After his Greatest Hits package came his next studio album, 1998's Leave a Mark. Also produced by Petocz, the album included bassist Mike Brignardello, steel guitar player Bruce Bouton (of Garth Brooks's studio band the G-Men), drummers Vinnie Colaiuta and Shannon Forrest, rhythm guitarist Biff Watson, and backing vocalist John Wesley Ryles. The track "You're the Ticket" was later recorded by Billy Hoffman, whose version was a single in 2000. Montgomery co-wrote the title track with Elbert West, who would later record the song himself in 2001. The project's lead single was "Love Working on You", written by Jim Collins and Craig Wiseman. It was followed by the top-five hits "Cover You in Kisses" and "Hold On to Me" between late 1998 and early 1999. The latter was also a top-40 hit on the Hot 100. Writing for MusicRow magazine, Ron Young thought that Montgomery's vocals were stronger than on previous albums. He also thought that Petocz's production was "crisp and clear", although he felt some of the songs had "lightweight" lyrics. The album was certified gold after release, honoring shipments of 500,000 copies.
Montgomery ended the 1990s with his sixth studio release, Home to You (1999). Its lead single was the Jeffrey Steele composition "Hello L.O.V.E.", which peaked at fifteen on the country charts. After it was the title track at number two. The third and fourth singles, "Nothing Catches Jesus by Surprise" and "You Are", both fell short of the top 40. Chad Brock later charted his own rendition of "You Are" between late 2003 and early 2004. Garth Fundis produced the album, and contributed backing vocals to both the title track and "Nothing Catches Jesus by Surprise". Both the latter and "Your Love Lingers On" were co-written by Waylon Jennings. Jason Sellers and Rebecca Lynn Howard respectively co-wrote the tracks "Love Made Me Do It" and "Love Is Our Business", and provided backing vocals to their compositions. Erlewine noted that the album was more focused on ballads than previous efforts, and thought its tracks had the potential to be serviced to adult contemporary formats. Country Standard Time writer Jeffrey B. Remz observed that four of the ten songs had the word "love" in the title, and thought the album's songs were "no different than sappy ballads from previous efforts", although he also thought the inclusion of instruments such as fiddle and Dobro retained a country sound.
In 2000, Montgomery released his seventh album Brand New Me. He co-produced the project with Buddy Cannon (best known for his work with Kenny Chesney) and Norro Wilson. Lead single "The Little Girl", featuring backing vocals from Alison Krauss, became his seventh and final number-one on the Billboard country charts by year's end. Songwriter Harley Allen wrote the song after reading a story e-mailed to him by his brother, about a child who claims to see Jesus after witnessing her parents' death via murder-suicide. Snopes considered the story an urban legend, and a "fairly typical example" of inspirational contemporary folklore circulated via e-mail at the time. "The Little Girl" was nominated by the Academy of Country Music for both Single and Song of the Year. Despite the success of this song, the follow-up singles "That's What I Like About You" and "Even Then" both failed to reach top 40 of the country charts. The album certified gold by the end of 2000. Maria Konicki Dinoia of AllMusic thought the stories of "Bus to Birmingham" and "Even Then" would appeal to fans of Montgomery's ballads, and that "Brand New Me" and "That's What I Like About You" would do likewise to fans who preferred his more up-tempo songs such as "Sold".

### 2002–2004: Pictures and Letters from Home

Following the closure of Atlantic Records's country music division in 2001, Montgomery transferred to the Nashville branch of parent company Warner Records. After doing so, he began recording his first Warner album, Pictures. Montgomery began recording the album in February and Warner released it in October. It was preceded by 47 concerts in the year 2001, all of which he had to perform while on crutches after breaking his shin. Pictures also reunited him with Hendricks as his producer. Sixwire (also recording on Warner at the time) provided backing vocals to the track "It Goes Like This", which was co-written by their lead guitarist Steve Mandile. The album's lead single was "'Til Nothing Comes Between Us", co-written by Kerry Kersh. While this song peaked in the top 20 of Hot Country Songs, follow-ups "Country Thang" and "Four Wheel Drive" were unsuccessful on the charts. Country Standard Time writer Dan MacIntosh said of the album, "He has nothing new to say here, nor does he come up with any novel ways to say the old things."
This project was followed in 2003 by a second compilation, The Very Best of John Michael Montgomery. The project included most of his hit singles as well as two new tracks, "One Day Less" and "Cool", both produced by Byron Gallimore. The latter was also sent to radio as a single. It was followed later in the year by Mr. Snowman, a Christmas album. The album included a mix of traditional Christmas songs such as "O Holy Night" and "Rudolph the Red-Nosed Reindeer", as well as the original "A Daddy's Prayer". Brian Wahlert of Country Standard Time criticized Montgomery's singing as "vanilla" on most of the tracks, but praised the same on "A Daddy's Prayer". After these was his last Warner album, Letters from Home, in 2004. Also produced by Gallimore, this album accounted for his last top-ten country hit in its title track, which spent four weeks at number two on the country charts and accounted for his highest Hot 100 peak of number 24. The only other single from the album was "Goes Good with Beer". Erlewine wrote of this project that it "showcases the country crooner what he does best: smoothly singing heartache tunes, odes to the past, and love songs. It may not be a new beginning, but fans aren't likely to complain, either." After Letters from Home, Montgomery ended his contract with Warner; he stated in 2007 that he chose to leave Warner as he thought the label was focusing more heavily on finding new artists than promoting existing ones.

### 2005–2024: Time Flies and retirement

Montgomery made no new recordings in 2005 or 2006 after exiting Warner, although he continued to tour. In late 2007, Montgomery announced he was founding a new independent record label called Stringtown Records. Shelia Shipley Biddy served as the label's president. Montgomery also announced that he planned to release an album through the venture in 2008, with Gallimore still serving as his producer. Montgomery stated that he chose to form his own label instead of signing with another one because he thought that most of the major country labels were going through mergers and acquisitions, while independent labels were becoming more popular by comparison. His only Stringtown album, Time Flies, came out in 2008. The album accounted for his last solo chart entry, the James T. Slater composition "Forever". Montgomery observed at the time that he did not have a radio single for about four years before "Forever", and that the long hiatus caused many radio stations to ignore the song. Similarly, he felt that radio programmers had begun to perceive him as an "older" artist, despite him being approximately the same age as contemporarily successful artists such as Keith Urban or Kenny Chesney. Reviewing the album for Country Standard Time, Jacquilynne Schlesier thought the album was largely too similar to his previous releases, although she praised the lyrics of "Drunkard's Prayer", "All in a Day", and "Brothers 'til the End". In 2009, Montgomery provided guest vocals on country rap artist Colt Ford's "Ride Through the Country", a single from his album of the same name. This song accounted for Montgomery's 36th and final entry on Hot Country Songs.
Although he released no further albums, Montgomery continued to tour throughout the 2010s. One such concert during the former year was held at Naval Air Station Pensacola in Pensacola, Florida. In 2010, he founded a company called Montgomery Mix Pro, with the intent of assisting new artists in creating and assessing demo recordings for new artists to promote themselves. He said that both this venture and the founding of his own label were in response to his perception that the country music industry was more focused on making money and appealing to demographics, as opposed to creating music that was desired by fans. In 2011, Montgomery performed with Lorrie Morgan at Pine Knob Music Theatre in suburban Detroit. According to The Flint Journal, Montgomery considered himself a fan of Morgan's music, as well as that of Keith Whitley, to whom she is a widow. At the time, he also expressed interest in creating a live album interspersed with stories about the creation of each song.
In 2016, he said in an interview with the El Paso Times that he still enjoyed touring despite having not released new music in several years because he "love[d] to get on stage". He once again underwent vocal cord surgery in 2019, this time to remove a polyp that had formed on one of his vocal cords. Montgomery's tour bus overturned in a road accident near the Kentucky-Tennessee state line in 2022. The accident broke several of Montgomery's ribs. Soon after the accident, Montgomery released a statement on Facebook that he was successfully recovering from the accident.
In January 2024, Montgomery announced that he would retire from touring at the end of his 2024-25 tour schedule, although he did not give a reason. That same year, he joined Post Malone on the stage of the Grand Ole Opry for a rendition of "Be My Baby Tonight" to honor Post Malone's debut at that venue.

## Musical style

Montgomery's musical style encompasses ballads and up-tempo material. Marjie McGraw, in The Encyclopedia of Country Music, thought that Montgomery "distinguished himself...with tender balladry" such as "I Love the Way You Love Me" and "I Swear"; she also described "Be My Baby Tonight" and "Sold (The Grundy County Auction Incident)" as "tongue twisters" in which he sang with a "manly baritone". Montgomery stated of his music in New Country magazine, "I want the youngest person and the oldest person to like it and understand it. It ain't too deep, but it ain't silly either." AllMusic writer Steve Huey describes Montgomery as "Part of the '90s wave of honky-tonk hitmakers that brought country to new commercial heights" and states that he "made his name primarily as a romantic balladeer. Yet despite his sometime adult contemporary leanings, his vocal style remained solidly grounded in country tradition." Schlesier stated in her review of Time Flies, "Since his debut in 1992, John Michael Montgomery built a solid career on a foundation of power ballads and uptempo humorous songs." Remz, in a review of The Very Best of John Michael Montgomery, thought Montgomery had a "pretty decent baritone" and noted that, unlike many of his contemporaries, Montgomery generally did not write his own songs. Remz also observed the singer's success with "up-tempo" songs such as "Sold (The Grundy County Auction Incident)" and "Be My Baby Tonight", while considering ballads such as "I Swear" to be "syrupy". Mansfield wrote of Montgomery's singing voice on his ballads, "[h]owever limited it may be, Montgomery's tender baritone cuts to the emotional core of 'I Can Love You Like That' and 'No Man's Land'...these songs are easy to sing along with, and they're easy to take to heart." Mansfield also opined that the covers of his songs by All-4-One, as well as his inclusion of Southern rock-styled electric guitar playing, showed that "[c]ountry folk have borrowed from pop music for generations". Montgomery has named Lionel Richie, Bob Seger, and George Strait as his main influences. He also stated that he personally selected songs he wanted to record, instead of relying on producers or song promoters to choose ones for him.
Montgomery was frequently contrasted with Garth Brooks. Colin Larkin, in The Virgin Encyclopedia of Country Music, wrote that "[i]n the mid-90s he stands as one of the hottest artists in country music, appealing to lovers of both Garth Brooks and Lynyrd Skynyrd." Of his concerts, Michael McCall of New Country magazine stated, "[h]e's not as rambunctious as Garth Brooks nor as showy as Neal McCoy, nor is he as still as George Strait or as reserved as Alan Jackson." McCall also noted positive reactions from female fans during ballads such as "I Swear", contrasted with his Southern rock influences as seen by the presence of multiple electric guitars in his road band, as well as Montgomery's own extended soloing during a performance of the Marshall Tucker Band's "Can't You See". Jack Hurst furthered the comparisons to Brooks in an article for the Chicago Tribune, as he thought the lyrical content of "Life's a Dance" was similar to Brooks's "The Dance", and the decision to include more upbeat material on Kickin' It Up comparable to "Friends in Low Places". Additionally, Hurst noted the "exaggerated, hillbilly-ish pronunciations and half-yodeled yips popularized by Brooks" in Montgomery's vocal delivery. Conversely, Hurst noted that Montgomery had a taller and thinner body type than Brooks, and also stated that he "isn't nearly as eloquent and talkative as Brooks." Montgomery himself stated that he appreciated such comparisons when they concerned his potential to have a broad appeal to country music fans in a similar fashion to Brooks, but not when others felt his musical style was derivative of Brooks's.

## Personal life

John Michael Montgomery's brother Eddie, with whom he performed in Early Tymz, worked as a member of his road crew in the 1990s. By the end of the decade, Eddie founded the duo Montgomery Gentry with Troy Gentry, also a former member of Early Tymz. Montgomery Gentry recorded for Columbia Records in the first decade of the 21st century and charted multiple hit singles in this timespan. Gentry died in a helicopter crash in September 2017, although Eddie has continued to tour under the Montgomery Gentry name. John Michael said in 2007 at the time of founding Stringtown Records that he had wanted to record with his brother, but could not do so when both were on major labels. The two brothers sang together for an acoustic concert at the Opera House in Lexington, Kentucky, in 2014. The song "Brothers 'til the End" from Time Flies is a tribute to Eddie. Both John Michael and Eddie are uncles of Dillon Carmichael, who is also a country music singer. John Michael Montgomery married Crystal White in 1996, and the couple had a daughter named Madison one year later. In 2023, Madison married country singer Travis Denning. Montgomery and White also have a son, Walker Montgomery, who released his own rendition of "I Love the Way You Love Me" in 2024.
Between 2005 and 2008, Montgomery was the subject of a number of publicized health and legal issues. At the Golden Corral 500, a NASCAR race held at Atlanta Motor Speedway, Montgomery opened the ceremonies with a performance of "The Star-Spangled Banner". He sang off-key and was visibly staggering throughout, causing many fans to believe he was drunk. In response, he issued an apology on his website, revealing he had been diagnosed with acoustic neuroma, a tumor on his inner ear which was negatively affecting his hearing and balance. In February 2006, Montgomery was arrested in Lexington, Kentucky, for driving under the influence, carrying prescription painkiller Endocet in an open container, and two counts of carrying a concealed weapon. Montgomery's attorney issued a report stating that Montgomery had permits for both of the weapons found in his car, as well as a prescription for the Endocet following a then-recent hip replacement surgery. An attorney working on the case discovered a MySpace page maintained by the arresting officer, which contained "congratulatory comments" left by other officers as well as altered photographs of Montgomery. In August 2006, Montgomery entered a plea deal which included paying over $600 in fines; the concealed weapon and prescription medicine charges were also dropped. Country Standard Time reported in May 2008 that Montgomery canceled a month's worth of concerts to enter drug rehabilitation after experiencing sleep disorder and anxiety issues, which resulted in the abuse of presctiption painkillers. According to The Boot, Montgomery exited rehabilitation prior to the release of Time Flies.

## Discography
### Studio albums

* Life's a Dance (1992)
* Kickin' It Up (1994)
* John Michael Montgomery (1995)
* What I Do the Best (1996)
* Leave a Mark (1998)
* Home to You (1999)
* Brand New Me (2000)
* Pictures (2002)
* Letters from Home (2004)
* Time Flies (2008)

### Billboard number-one hits

* "I Love the Way You Love Me" (3 weeks, 1993)
* "I Swear" (4 weeks, 1993–1994)
* "Be My Baby Tonight" (2 weeks, 1994)
* "If You've Got Love" (1 week, 1994)
* "I Can Love You Like That" (3 weeks, 1995)
* "Sold (The Grundy County Auction Incident)" (3 weeks, 1995)
* "The Little Girl" (3 weeks, 2000)

## Awards and nominations
### Grammy Awards

| Year | Nominee / work | Award | Result |
| 1995 | "I Swear" | Best Male Country Vocal Performance | Nominated |
| 1996 | "I Can Love You Like That" | Best Male Country Vocal Performance | Nominated |
| 1996 | John Michael Montgomery | Best Country Album | Nominated |

### Academy of Country Music Awards

| Year | Nominee / work | Award | Result |
| 1994 | John Michael Montgomery | Top New Male Vocalist | Won |
| 1994 | "I Love the Way You Love Me" | Song of the Year | Won |
| 1995 | "I Swear" | Song of the Year | Won |
| 1995 | "I Swear" | Single Record of the Year | Won |
| 1996 | "Sold (The Grundy County Auction Incident)" | Video of the Year | Nominated |
| 2000 | "The Little Girl" | Single Record of the Year | Nominated |
| 2000 | "The Little Girl" | Song of the Year | Nominated |

### Country Music Association Awards

| Year | Nominee / work | Award | Result |
| 1993 | John Michael Montgomery | Horizon Award | Nominated |
| 1994 | John Michael Montgomery | Horizon Award | Won |
| 1994 | "I Swear" | Single of the Year | Won |
| 1995 | John Michael Montgomery | Male Vocalist of the Year | Nominated |
| 1995 | John Michael Montgomery | Album of the Year | Nominated |