Ranking All 57 of Madonna’s Billboard Hits in Honor of Her 60th(!) Birthday
By: Richard Lebeau
Tags: Hollywood, Celebrity, Music, Pop Culture, Culture

Madonna Louise Ciccone, better known simply as Madonna, was born 60 years ago today — August 16, 1958. She was born in Bay City, Michigan to devoutly Catholic parents and her mother died of breast cancer when she was 5. She became a rebellious teen and dropped out of college at the age of 20, opting instead to pursue a career in dance in New York City. Five years after arriving in New York, she released her eponymously titled debut album. A few months after the album’s release, Dick Clark invited her to perform on American Bandstand. Before she took the stage Clark asked, “What do you hope will happen, not only in 1984 but for the rest of your professional life? What are your dreams? What’s left?” Without hesitation Madonna gave her legendary answer: “To rule the world.”

And she did rule the world. At least the pop music world. The undisputed “Queen of Pop,” Madonna has an astonishing array of richly deserved superlatives. With over 300 million records sold, she is the best-selling female recording artist of all time. With a record 38 Top 10 songs, she is the most successful solo act in the history of the Billboard Hot 100 Chart. With box office receipts totaling over $1.4 billion (unadjusted for inflation), she is the highest grossing solo touring artist of all time. She has won a bevy of awards, including 7 Grammys, 2 Golden Globes (one for acting and one for songwriting), and an eye-popping 20 MTV Video Music Awards. She was inducted into the Rock and Roll Hall of Fame in 2008.

To be fair, she has had her share of high profile failures. Some of her musical reinventions were markedly less successful than others, particularly in recent years. Despite appearing in several hit films like Desperately Seeking Susan, Dick Tracy, and A League of Their Own, she never successfully launched a career as an actress (and in fact has amassed more Razzie Awards than any other actress in history). And, to be honest, more often than not the controversies stirred by the boundary-pushing iconoclast feel more about grabbing headlines than truly making a statement.

But despite her misses and her icy public persona, Madonna is an undisputed music legend. She has crafted some of the best pop songs of all time, revolutionized the art of the music video, and redefined the touring model. She has diversified into multiple successful business ventures and has maintained a tremendous amount of autonomy throughout her 35 year career. And arguably she is the last living pillar of 1980s popular music following the deaths of Michael Jackson, Whitney Houston, and Prince in the past decade.

In honor of her 60th birthday, I decided to rank all of her songs that charted on the Billboard Hot 100, which coincidentally also turned 60 less than 2 weeks ago. She has made 57 entries on the chart, nearly one for every year of her life. Revisiting 35 years of her hits to make this list was a wildly entertaining ride, one I highly recommend.

Note: This is not a list of what I think are the best songs Madonna has ever made, nor is it a ranking of her most popular or influential songs. Due to her vast back catalogue, I limited this list to songs that charted on the Billboard Hot 100. The rankings are based on my assessment of each songs overall merit in terms of songwriting, composition, vocals, and production. Just about everyone will disagree with my ranking, but that’s part of the fun.

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57. “Bitch I’m Madonna” (2015; Billboard Peak: 84) Madonna’s most recent album, 2015’s Rebel Heart, was a wildly uneven 22-track epic that had some truly brilliant songs. Unfortunately, the only song to chart from the album — this obnoxious, juvenile collaboration with Nicki Minaj — was not one of them.

56. “American Life” (2003; Billboard Peak: 37) Perhaps the biggest commercial and critical failure of Madonna’s career, the lead single from her disastrous 2003 album of the same name is almost listenable until the 3 minute and 10 second mark where she breaks into one of the most ill-conceived rap breaks in music history. (Sample lyrics include: “I’m drinkin’ a soy latte/ I get a double shot-ay,” “I drive my Mini Cooper/ And I’m feeling super-duper,” and “I do yoga and pilates/ And the room is full of hotties/ So I’m checking out their bodies.”)

55. “American Pie” (2000; Billboard Peak: 29) It remains unclear why Madonna thought an abbreviated dance remake of Don McLean’s classic slice of Americana was a good idea. It wasn’t.

54. “Die Another Day” (2002; Billboard Peak: 8) This wildly overproduced and lyrically nonsensical song was written for the 20th James Bond film, which shared the same name. It assuredly ranks toward the bottom of any list of Bond themes and Madonna singles.

53. “Give Me All Your Luvin’” (2012; Billboard Peak: 10) Madonna’s 38th and most recent Top 10 single is this disposable and age-inappropriate ditty, which unnecessarily incorporates cheerleaders, a marching band, and raps by Nicki Minaj and M.I.A.

52. “Causing a Commotion” (1987; Billboard Peak: 2) There is nothing especially bad about this track from the soundtrack of Who’s That Girl? but it is profoundly forgettable, particularly in comparison with the brilliant singles that preceded and followed it.

51. “Keep it Together” (1990; Billboard Peak: 8) The fifth single from the terrific Like a Prayer album, this one pales in comparison to the four that preceded it and has not aged well.

50. “Hanky Panky” (1990; Billboard Peak: 10) Perhaps the strangest of Madonna’s hits and perhaps the most unlikely Top 10 hit of the 1990s, this track from her Dick Tracy-inspired album is a throwback jazz and swing song with bawdy lyrics that certainly gets points for its boldness and audacity. Yet it never truly rises above its novelty status.

49. “Celebration” (2009; Billboard Peak: 71) Clearly designed exclusively for the clubs and probably written and produced in the span of an hour, this song is hardly the best of her dance club hits, but it works much better than it needs to.

48. “Angel” (1985; Billboard Peak: 5) This sweet and catchy ditty features one of her better early vocal performances but deviates too little from the template of her early tracks to be a standout.

47. “Bedtime Story” (1995; Billboard Peak: 42) This song was far more famous for its music video (which at the time was the most expensive ever made) than for the quality of the song, but its undoubtedly intriguing in its lyrics and production and clearly set the stage for the Ray of Light era.

46. “Nothing Really Matters” (1999; Billboard Peak: 93) This is a perfectly fine cut from her best album (Ray of Light), but there are several other songs on the album that are better and would have made more interesting singles.

45. “Me Against the Music” (2003; Billboard Peak: 35) Many found this hotly anticipated collaboration between Madonna and Britney Spears to be underwhelming. Although it clearly doesn’t rank as either of their best songs, it has an infectious beats and has some moments that really work.

44. “4 Minutes” (2008; Billboard Peak: 3) Much like the above collaboration with Justin Timberlake’s famous ex-girlfriend, this collaboration with Timberlake and Timbaland is a serviceable dance floor hit that doesn’t soar.

43. “Who’s That Girl?” (1987; Billboard Peak: 1) In a Season One episode of the Netflix comedy Unbreakable Kimmy Schmidt, Lillian (Carol Kane) asks “Who’s That Girl?” Kimmy answers, but it turns out Lillian was watching Jeopardy and the category was “Worst Madonna Songs.” The Clue: “This 1987 one is terrible.” Terrible is a strong word, but it is most definitely not one of her best.

42. “You Must Love Me” (1996; Billboard Peak: 18) This Oscar-winning song was written by Tim Rice and Andrew Lloyd Weber for the film version of their stage musical Evita, in which Madonna starred as legendary Argentinian first lady Eva Peron. It is exceedingly earnest and not particularly interesting as a song, but it does feature one of the strongest and most elegant vocal performances Madonna has ever delivered.

41. “Beautiful Stranger” (1999; Billboard Peak: 19) Significantly more successful than her stab at a James Bond theme (see #54) was this theme song for the blockbuster Bond spoof Austin Powers: The Spy Who Shagged Me. It’s bold and clever and interestingly bridges the Ray of Light and Music eras.

40. “Love Don’t Live Here Anymore” (1996; Billboard Peak: 78) This song had a very strange evolution. It was a minor hit from 1978 by Rose Royce that Madonna first covered on her second studio album (Like a Virgin). A reworked version was featured on her 1995 ballad compilation Something To Remember. It was this version that charted. It marks a rare but intriguing and largely successful foray into remakes.

39. “Don’t Cry for Me Argentina” (1997; Billboard Peak: 8) She’s no Patti LuPone (the Tony-winning Broadway legend performed the definitive version of this song), but her vocals are excellent and the song is beautifully composed. It was elevated on the charts by its dance remix, which is bizarre in theory but works terrifically in execution.

38. “True Blue”(1986; Billboard Peak: 3) Despite being a huge hit and the title track off one of her biggest albums, Madonna excluded this song from her 1990 greatest hits compilation The Immaculate Collection. It’s a charming pop ditty with no significant flaws, but clearly even Madonna knew then that it wasn’t a standout in her catalogue.

37. “Bad Girl” (1993; Billboard Peak: 36) Despite what I consider to be one of her weaker vocal performances, this song was justly praised by critics for its mature lyrical composition as it tells the story of a woman experiencing shame at her behavior in the aftermath of a breakup.

36. “Oh Father” (1989; Billboard Peak: 20) This affecting pop ballad found Madonna getting much more personal than usual as she explores her complicated dynamics with her father.

35. “You’ll See” (1995; Billboard Peak: 6) Both the song and music video were intended as a sequel of sorts to the hit ballad “Take a Bow.” It never quite reaches the heights of that Babyface-assisted chart topper, but this collaboration with legendary songwriter and producer David Foster is one of her stronger ballads.

34. “Lucky Star” (1983; Billboard Peak: 4) Madonna’s first smash hit that hasn’t aged particularly well but is nevertheless an iconic and catchy early ’80s pop gem that clearly announced her arrival.

33. “Give it 2 Me” (2008; Billboard Peak: 57) Madonna collaborated with Pharrell Williams on this upbeat, anthemic dance song about her perseverance in the music industry. With its clever lyrics and unique percussion, this is a truly underrated song in her catalogue.

32. “What it Feels Like for a Girl” (2001; Billboard Peak: 23) Some of Madonna’s best lyrics can be found in this tenderly executed indictment of society’s harmful treatment of young women and with better production it could have been a true classic.

31. “Dress You Up” (1985; Billboard Peak: 5) Sure, it’s juvenile and earnest and doesn’t stray too far from the formula of her early hits, but it’s a clever, compulsively listenable dance-pop song.

30. “Rescue Me” (1991; Billboard Peak: 9) This collaboration with Shep Pettibone, the record producer who helped Madonna craft “Vogue” a year earlier, closed out The Immaculate Collection with a gospel-tinged anthem that combines some of the best elements of “Like a Prayer,” “Express Yourself,” and — yes — “Vogue.”

29. “Crazy For You” (1985; Billboard Peak: 1) The theme song from the long-forgotten film Vision Quest was this memorable Madonna ballad, which was her first hit that found a home on adult contemporary radio rather than the clubs.

28. “Sorry” (2006; Billboard Peak: 58) The second single released from her terrific Confessions on a Dance Floor is a disco-infused banger that marks one of the best songs of her later career.

27. “Holiday” (1983; Billboard Peak: 16) Madonna’s first chart hit was this infectious call to party that has some trite lyrics but an undeniable beat that has become ingrained in popular culture.

26. “Live To Tell” (1986; Billboard Peak: 1) The haunting lead single from True Blue, is moody, mysterious, and — at nearly 6 minutes — massive. Its quite opaque (and admittedly a bit too long), but its mature lyrics and elegant vocals marked a major change for Madonna.

25. “Human Nature” (1995; Billboard Peak: 46) One of Madonna’s best forays into R&B, this all-around-clever song features bold, unapologetic lyrics that serves as her unofficial manifesto. (Sample lyric: “Did I say something true? Oops, I didn’t know we couldn’t talk about sex/ Did I have a point of view? Oops, I didn’t know we couldn’t talk about you.”)

24. “Cherish” (1989; Billboard Peak: 2) After the first two singles from Like a Prayer boldly tackled themes of religion and sexuality, Madonna switched things up for this optimistic, wholesome, and romantic pop song that is one of the most joyful that she has ever recorded.

23. “Rain” (1993; Billboard Peak: 14) One of the best ballads of Madonna’s career, this mature and heartfelt ballad never got the attention or respect it deserved (probably because it was released amidst the most controversial stage of her career.)

22. “Don’t Tell Me” (2000; Billboard Peak: 4) Madonna demands independence from her lover on this fascinating merge of country and dance that ranks high among the most unique songs of her career.

21. “I’ll Remember” (1994; Billboard Peak: 2) This moving ballad was a better theme song than the forgettable film With Honors deserved. It effectively merges synthesizers, beautiful background vocals, mature vocals, and tearjerking lyrics.

20. “Material Girl” (1985; Billboard Peak: 2) It may present Madonna at her vainest and the lyrics may be immature and dated, but the fact is that this is one of the most iconic songs of the 1980s for a reason — its brilliant pop music.

19. “The Power of Goodbye” (1998; Billboard Peak: 11) One of the most underrated songs of Madonna’s career, this melancholy electronica ballad is one of her most deeply affecting. (Sample lyric: “Your heart is not open so I must go / The spell has been broken, I loved you so / Freedom comes when you learn to let go / Creation comes when you learn to say no / You were my lesson I had to learn / I was your fortress you had to burn / Pain is a warning that something’s wrong/ I pray to God that it won’t be long.”)

18. “Erotica” (1992; Billboard Peak: 3) The wild controversy surrounding the music video and accompanying book, both of which explicitly portrayed S&M, overshadowed the fact that this is one of the most innovative songs of Madonna’s career. It is an orgy of hip hop and electronica, with spoken word verses, a killer bridge, and an infectious chorus.

17. “Borderline” (1984; Billboard Peak: 10) One of the highlights of Madonna’s early career, this flawless pop song features brilliant production and strong vocals.

16. “Take a Bow” (1994; Billboard Peak: 1) To the surprise of many, this soulful ballad written and produced with R&B super producer Kenneth “Babyface” Edmonds is Madonna’s longest running #1 hit. It features one of her most nuanced vocal performances and some of the most poetic lyrics of her career.

15. “La Isla Bonita” (1987; Billboard Peak: 4) Madonna’s romanticism (perhaps fetishization) of Latin culture probably wouldn’t play well if released in today’s age of sensitivity to cultural appropriation, but her incorporation of Spanish lyrics and diverse instrumentation (including Spanish guitars and Cuban drums) make this one of the most unique and memorable songs in her catalogue.

14. “Like a Virgin” (1984; Billboard Peak: 1) Probably Madonna’s most iconic song, it endures in popular culture for reasons other than the infamous MTV Video Music Awards performance in the wedding dress. It is stunning pop that merges provocative lyrics, a synth-fueled baseline, and a classic melody.

13. “Open Your Heart” (1986; Billboard Peak: 1) Originally a rock-oriented song written for Cyndi Lauper, Madonna and frequent collaborator Patrick Leonard reworked the song into a rousing, infectious, innuendo-laden dance-pop spectacular.

12. “Music” (2000; Billboard Peak: 1) Madonna’s most recent #1 hit, this bold and aggressive electro-funk song may not be particularly lyrically inspired (“Music makes the bourgeoisie and the rebel”… do what exactly?) but it is rightfully hailed as one of her finest and most unexpected hours by music critics.

11. “Ray of Light” (1998; Billboard Peak: 5) The lyrics may be utterly nonsensical, but this warm, upbeat, EDM anthem starts slow and gradually builds to an utterly frenetic climax. It’s an entrancing roller coaster for its entire 5 and a half minute duration.

10. “Hung Up” (2005; Billboard Peak: 7) It may combine lyrics from her Prince collaboration “Love Song” and heavily sample ABBA’s “Gimme! Gimme! Gimme! (A Man After Midnight)” but somehow the song feels bold and fresh. It is arguably the best disco song of the past 20 years and the last masterpiece Madonna has given us to date.

9. “Secret” (1994; Billboard Peak: 3) This seductive and soulful ballad was the first single off of her tepidly received foray into R&B (Bedtime Stories), but nevertheless is a highlight of her career. The genre-blurring song combines an entrancing melody, acoustic guitar, passionately felt vocals, and intriguing lyrics.

8. “Deeper and Deeper” (1992; Billboard Peak: 7) My vote for the most underrated of all of Madonna’s hits, this disco anthem is 5 and a half minutes of pure bliss that marks another masterful collaboration between Madonna and Shep Pettibone.

7. “Frozen” (1998; Billboard Peak: 2) The lead single of her most acclaimed album (Ray of Light) exemplifies why her transformation into a goddess of electronica and spirituality was her most successful. The entrancing melody, grand production values, and epic length led many critics to declare it a masterpiece upon its release.

6. “This Used to Be My Playground” (1992; Billboard Peak: 1) When Madonna was asked to write and record a song for the Geena Davis-Tom Hanks film A League of Their Own (in which she costarred), one might have expected that she would have gone for a ’40s inspired swing song (a la her Dick Tracy inspired collection.) Instead she went for a gut-wrenching ballad that explores themes related to nostalgia, grief, and heartbreak. In my opinion, this is the best ballad of her career and one of the best ballads of the 1990s.

5. “Justify My Love” (1990; Billboard Peak: 1) This genre-defying song is a downtempo, sensuous slow-burn. Co-written and produced by Lenny Kravitz (and also featuring passionate backup vocals from him), this song features breathy spoken word passages conveying intense sexual longing over fresh beats. It is hardly her most accessible and crowd-pleasing song but it is an innovative and distinctive masterpiece.

4. “Express Yourself” (1989; Billboard Peak: 2) This dance-pop anthem is a call to arms for all women to demand more — from their men and from society. Its inspiring and empowering message aside, it’s also just damn good pop music. With its insanely catchy chorus, commanding vocals, and horn-fueled instrumentation, it is one of the best pop songs of the 1980s.

3. “Papa Don’t Preach” (1986; Billboard Peak: 1) Madonna’s biggest controversy-generator to date at the time of its release, this song told the story of a young woman’s unplanned pregnancy that throws her life into turmoil and strains her relationship with her traditional father. The lyrics are sophisticated and Madonna’s gritty, lower-register vocal performance perfectly conveys their power.

2. “Vogue” (1990; Billboard Peak: 1) Even excluding the majesty of its legendary music video and seriously considering the reasonable allegations of cultural appropriation, this song is a masterwork. The trendsetting house song features straightforward and empowering lyrics, brilliant pacing and structure, and exquisite production. It is quite possibly the best dance song ever made.

1. “Like a Prayer” (1989; Billboard Peak: 1) Perhaps Madonna’s most controversial song, this gospel-infused pop anthem provocatively united religious imagery with sexual innuendo and had an equally scandalous video. It’s a shame that the controversy dominated so much of the song’s legacy as it is one of my nominees for best pop song ever made. It’s a riveting, slow building, and ultimately transcendent piece of popular music that only gets better with repeated listens.

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Bonus: 13 Great Madonna Songs that Should Have Charted!

“Everybody” (1982)

“Burning Up” (1982)

“Into the Groove” (1985)

“Love Song” (Duet with Prince; 1989)

“Swim” (1998)

“Be Careful (Cuidado Con Mi Corazon)” (Duet with Ricky Martin; 1999)

“Deserve It” (2000)

“Hollywood” (2003)

“Nothing Fails” (2003)

“Push” (2005)

“Miles Away” (2008)

“Ghost Town” (2015)

“Rebel Heart” (2015)

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