Producer Patrick Leonard likes to recount the story that Madonna wrote the lyrics to “Live To Tell” on a legal pad while sitting on the floor of his living room. The demo vocal, recorded on an 8-track player also in Leonard’s house, is the version used on the hit from 1986’s “True Blue” album.
It’s easy to forget that along with the leonine dance moves, savvy selling of sex and chameleonic maneuvers to remain relevant, Madonna was an expert songwriter possessed by innate scrappiness.
She’s among an elite few to have a hit in five distinct decades – including 12 No. 1s on the Billboard Hot 100 – and those songs routinely set their own agenda. Whether detouring into techno, Auto-Tuned pop, electro-coated country, Latin or modern disco, Madonna was usually the one setting trends while others followed.
On the occasion of her 65th birthday, we salute Madonna Louise Ciccone for her staggering catalog, which we will see commemorated on stage during her Celebration tour , and rank 65 of her best songs.
65. ‘Bitch I’m Madonna,’ featuring Nicki Minaj (2015)
It doesn’t get more meta than Madonna telling you how great it is to be Madonna. Released during her gold teeth grills phase – aka the period around her “Rebel Heart” release – Madonna and producer Diplo mold her her squeaky vocals to rubbery synths that pump along until Minaj swoops in to clarify for those not following along: “I’m bossed up, I got ’em awestruck, it’s not a toss-up, I’m the winner.” She’s rapping about Madonna, of course.
64. ‘Best Friend’ (2012)
Though it starts with an icy machine gun cadence, the lyrics soon make it clear that this EDM-heavy track from “MDNA” is a forlorn account about Madonna missing the someone who made her laugh and wrote her poetry. But, she admits, while she yearns for the good times, “I don’t miss all of it.”
63. ‘Hanky Panky’ (1990)
Inspired by her role as Breathless Mahoney in “Dick Tracy,” Madonna turned to the dominant musical styles of the film’s 1930s setting – jazz and swing – and unveiled a slinky persona to match. Only the Queen of Pop, unapologetic as ever, could sell the line “nothing like a good spanky” without sounding (too) ridiculous.
62. ‘Die Another Day’ (2002)
Stilted electronica made this far from a remarkable James Bond theme – which we prefer stirred with grandeur – but upon repeated listens, there is something intriguing about its chilly construction.
61. ‘Celebration’ (2009)
Released as one of two new tracks on her greatest hits album of the same name, the buzzing club thumper – polished by co-producer Paul Oakenfold – winks at her ‘80s pop hits with its unabashed call to party.
60. ‘Give it 2 Me’ (2008)
Instantly recognizable with the fingerprints of Pharrell Williams, who co-wrote and co-produced the track, with jangles of West African percussion and a snaking cadence. The midsong “get stupid” breakdown is repetitive and silly, but will also bury in your brain.
![Pop singer Madonna performs with a male dancers during her "Girlie Show" concert at Wembly Stadium in London, England on Sept. 25, 1993. (AP Photo/Gill Allen) ORG XMIT: APHSL0015 [Via MerlinFTP Drop]](https://feeds.feedblitz.com/gcdn/presto/2022/10/18/USAT/32e02604-fc97-4c0c-bd23-90967b2df60c-XXX_AP9309250331_dcb.jpeg?width=300&height=380&fit=crop&format=pjpg&auto=webp)
59. ‘I Love New York’ (2005)
The album track from “Confessions on a Dance Floor” is a lyrically slight valentine to the city that birthed her career. “No other city ever made me glad except New York,” Madonna sings (take that, Randy Newman) as she paints the city as a place where only the strong-willed survive. Others can, pointedly, “get off my street.”
58. ‘Erotica’ (1992)
Madonna’s taboo-breaking fifth album of the same name blended pop with hip-hop, while the single married taste with smut. Assuming the persona of a dominatrix, Madonna is bold and experimental as she wields lyrics about sadomasochism. A track truly ahead of its time.
57. ‘She’s Not Me’ (2008)
Keeping in the spirit of her “Hard Candy” album – some funk, some disco, some R&B – Madonna cavorts over a Chic-inspired guitar riff and clip-clopping beat and reminds us that you can mimic her hairstyle, you can reproduce her outfits, but there is only one Madonna.
56. ‘Love Don’t Live Here Anymore’ (1984)
This cover of the 1978 Rose Royce ballad was the anomaly alongside the synthesized pop on the rest of the “Like a Virgin” album. While never a hit, the song pushed Madonna to record with a live orchestra for the first time and the overwhelming scenario resulted in her emotional read.
55. ‘Gambler’ (1985)
A hit in several countries – but not the U.S. because it was never released as a single – the companion to “Crazy For You” from the “Vision Quest” soundtrack is an upbeat chunk of young Madonna attitude. Fans often lamented that the urgent dance track – only available on the soundtrack – was a smash in waiting. In December 2022, Madonna unlocked the song to streaming services.
54. ‘Rebel Heart’ (2015)
The title track to her 13th album is impelled by acoustic guitars, strings and a full chorus that details her emotional stamina. The unfussy production spotlights Madonna’s autobiographical lyrics, which include how she still can’t shake the voice of her father from chastising her non-conformist ways.
53. ‘Love Makes the World Go Round’ (1986)
Madonna debuted the cheerful tambourine-banger – her first songwriting collaboration with producer Patrick Leonard – at Live Aid before the track landed as the optimistic closer on “True Blue.”
52. ‘The Power of Goodbye’ (1998)
Often compared (for good reason) to “Frozen” for its sonic similarities, the electronica ballad finds Madonna singing about the strength in letting go and lessons learned (“pain is a warning something is wrong”). The plaintive chorus mesmerizes with one of the most nuanced vocals of her massive catalog.
51. ‘Human Nature’ (1994)
Repeatedly whispering “Express yourself, don’t repress yourself” as the song opens sets the scene of this TLC-esque thumper. Madonna is clearly annoyed about the pushback of the previous two years from her “Sex” book, “Erotica” album and “Body of Evidence” film, as she snarkily interjects, “Oops, I didn’t know I couldn’t talk about sex.”
50. ‘Burning Up’ (1983)
A dash of serrated guitar and propulsive beat do not a superstar make. But what this early single from Madonna’s self-titled debut spotlighted was the rare kind of sexual energy, magnetism and lyrical delivery that collide to create an icon.
49. ‘Justify My Love’ (1990)
Frank, breathless and with a muscular, throbbing rhythm, the single from her “The Immaculate Collection” anthology spellbinds as Madonna speak-sings her way through the sensual lyrics, written with Lenny Kravitz and Ingrid Chavez. Don’t lie. You know you were intrigued.
48. ‘Drowned World/Substitute for Love’ (1998)
The opening track on her ‘Ray of Light” album indicates the life changes Madonna experienced in the preceding couple of years – giving birth to daughter Lourdes, starring in “Evita” and learning about Kabbalah among them – which she recounts over a slow-burn beat. Released around the time she turned 40, the song is clearly Madonna’s entry into middle-aged reflection.
47. ‘Medellin,’ featuring Maluma (2019)
Ignore the wacky Madame X persona Madonna created for her 14th album (called, of course, “Madame X”) and focus instead on the mellow pulse of the Latin-infused song and the spice inserted by hunky Colombian singer Maluma. An atmospheric triumph that again showcased Madonna’s genre-mashing wizardry.
46. ‘American Life’ (2003)
No, it isn’t a patriotic song, but one that sharply – both lyrically and audibly – exposes the shallowness of American culture (“I got a lawyer and a manager, an agent and a chef/Three nannies, an assistant, and a driver and a jet”). It isn’t Madonna’s most graceful or tuneful offering – the beat is harsh and her rapping … well … yeah. But her point is salient.
45. ‘Another Suitcase in Another Hall’ (1996)
The mellifluous sigh of a song from Andrew Lloyd Webber and Tim Rice for “Evita” was originally recorded by Barbara Dickson in 1976 and flourishes under Madonna’s upper-range vocals, which are backed primarily by quiet acoustic guitar and an irresistible sax solo.
44. ‘Sorry’ (2005)
She’s heard it all before, so don’t waste time with empty apologies. Then again, if it means having to listen to this gem as it gradually builds to a disco-tastic gallop, please, keep apologizing.
43. ‘Everybody’ (1983)
The song that introduced Madonna to the world. Is it remarkable? Hardly, considering the pedestrian beat, of-their-era tinny keyboards and trite lyrics about getting up and dancing. But, like “Burning Up,” Madonna exudes a girlish allure. Talk about an evolution.
42. ‘Deeper and Deeper’ (1992)
The second single from Madonna’s “Erotica” album finds her on familiar terrain – a dance-house-pop-disco amalgamation flecked with references to “Vogue” and specks of flamenco guitars. It’s a fleeting moment of lightness.
41. ‘4 Minutes,’ featuring Justin Timberlake and Timbaland (2008)
Back when Timberlake was cool, Madonna smartly enlisted him and producer Timbaland, who packed his trademark clipped beats, as the first artists to be featured on one of her singles. The slick composition belies lyrics about saving the environment and other social ills.
40. ‘Cherish’ (1989)
Along with the title track from “True Blue,” this might be the most innocent Madonna has ever sounded. And that sound – so sweet, so perky, so open-hearted – is of a woman in love.
39. ‘Oh Father’ (1989)
It’s Madonna at her most vulnerable as she struggles to accept the loss of her mother (who died when Madonna was 5) and navigate her complicated relationship with her father. Piano, strings and violin generate the texture, but it’s Madonna’s wounded vocals as she cautiously sings, “you can’t hurt me now,” that pierce.
38. ‘Hollywood’ (2003)
Using the stereotype of people coming to Hollywood in search of fame as a launch pad, Madonna brandishes cynicism, compressed vocals and a glossy veneer as her weapons to shatter illusions.
37. ‘Secret’ (1994)
With producer Dallas Austin (TLC, Gwen Stefani) at the helm, the “Bedtime Stories” track edges from its acoustic guitar-based foundation to an intoxicating R&B heartbeat. Madonna rides the groove effortlessly.
36. ‘Hung Up’ (2005)
How best to craft a compelling disco-pop song? Sample ABBA. By utilizing the instrumental vein of the Swedish pop royals’ “Gimme! Gimme! Gimme! (A Man After Midnight),” Madonna conjured a modern disco classic. ABBA’s songwriters, Benny Andersson and Björn Ulvaeus, rarely granted permission to use the band’s music. Clearly, they knew they had a winning hand.
35. ‘Me Against the Music’ with Britney Spears (2003)
Though technically a Spears single (from her “In the Zone” album), the funky dance-pop collaboration is elevated by Madonna, one of many co-writers on the tune, who is much more than a feature. The pair trade lines, Madonna handles the bridge (“Hey, Britney, you say you wanna lose control…”) and injects cool maturity.
34. ‘Fever’ (1992)
Suffice to say that Little Willie John, the R&B singer behind the original 1956 version, and even Peggy Lee, who made it her signature song, probably never envisioned “Fever” morphing into a slinky dance track – i.e., given the Madonna makeover.
33. ‘True Blue’ (1986)
With nods to doo-wop and Motown – Madonna did grow up near Detroit – the song is a syncopated swish of joy. Inspired by her then-new marriage to Sean Penn, Madonna copped one of his favorite expressions about love for the title.
32. ‘Rain’ (1992)
Compared to the sultrier offerings on the “Erotica” album, this feathery R&B ballad leaped out because of its radio-friendly appeal. Madonna employs rain as a metaphor – washing away sorrow and pain to wipe the slate clean.
31. ‘Nothing Really Matters’ (1999)
While not as dynamic as much of the whole of her “Ray of Light” album, the sixth single from the release is noted not for its ambient electronica, but for Madonna’s realization that with motherhood comes change in perspective: “Now that I am grown, everything’s changed/I’ll never be the same because of you.”
30. ‘Don’t Cry for Me Argentina’ (1996)
Debates will continue about Madonna’s performance as Eva Perón in the film version of “Evita.” But when it comes to the unwrapping of the sumptuous Lloyd Webber/Rice anthem during the famed balcony scene, Madonna thoroughly nails the centerpiece of the story with sensational restraint.
29. ‘Angel’ (1984)
A simple dollop of synthesizers nudge the third single from “Like a Virgin.” Madonna has said the song is about her belief in angels based on her Catholic upbringing, but the lyrics also detour into romantic love (“I believe that dreams come true, ‘cause you came when I wished for you”).
28. ‘Causing a Commotion’ (1987)
Madonna told Rolling Stone that this contribution to the “Who’s That Girl” soundtrack was written out of frustration from her heated marriage to Sean Penn. She felt he was purposely distracting her, hence the robust dance track, “Causing a Commotion.”
27. ‘Beautiful Stranger’ (1999)
Tapping into her affinity for psychedelic sounds, Madonna landed the lead single from the soundtrack to “Austin Powers: The Spy Who Shagged Me.” Dreamy vocals, drum loops and guitar effects mesh into an engaging swirl.
26. ‘Dress You Up’ (1984)
The last single released from the Nile Rodgers-produced “Like a Virgin” album bubbles with dance-pop froth. Madonna oozes charm as she girlishly flits through sly sexual innuendo with an omnipresent audible grin.
25. ‘I’ll Remember’ (1994)
Proving (again) that she was about more than sex, Madonna tamed her post-“Erotica” image for a contemplative ballad on the soundtrack to “With Honors.” Its lyrics, tender with gratefulness to those who helped her find her way, and a vibrating keyboard background resound with sweetness.
24. ‘Who’s That Girl’ (1987)
Madonna pulled double duty as both star of the movie and chief of the soundtrack. This title track flirts with her affection for Latin pop, even presenting lyrics in English and Spanish, while maintaining an aura of mystique.
23. ‘Crazy for You’ (1985)
The primary hit from the “Vision Quest” soundtrack was also Madonna’s first foray into adult contemporary territory. Not only did the prom ballad ascend the charts – it was her second No. 1 on the Billboard Hot 100 – but also earned her first Grammy nomination (best female pop vocal performance, which she lost to Whitney Houston’s “Saving All My Love For You”).
22. ‘What it Feels Like for a Girl’ (2000)
A highlight on the “Music” album, its potent storytelling about the double standards endured by women and forthright tackling of illusions of female inferiority aren’t new topics for Madonna. But framed by downy keyboards, the lyrics gently hammer.
21. ‘This Used to Be My Playground’ (1992)
Written during a break in her “Erotica” sessions while also starring in “A League of Their Own,” Madonna shifted from the stimulating topics of her album in the works to pure introspection. The pensive ballad digs into grief and nostalgia and will leave a handprint on your heart.
20. ‘Live to Tell’ (1986)
Written on a legal pad on the floor of producer Patrick Leonard’s house, the song took shape when Madonna recorded a demo vocal on an 8-track player in the house. It was so good and so emotionally fulfilling, that first take became her first No. 1 on the adult contemporary chart while residing on the soundtrack to “At Close Range” and on her “True Blue” album.
19. ‘Don’t Tell Me’ (2000)
The stuttering country guitar that opens the song is so unique to Madonna’s sound that even when the high hat and bass drum kick in, it’s still evident that she’s embarked on a new musical journey. Lyrically, however, she remains defiant.
18. ‘Material Girl’ (1994)
While the tag “Material Girl” doesn’t really fit Madonna anymore – did it ever? – the synth-pop song with the spongy keyboards and lyrics about only wanting men who could understand her avarice is everlasting.
17. ‘Frozen’ (1998)
Coating the song with theatrical layers of synths – similar to “Drowned World/Substitute for Love” – Madonna creates a cinematic environment to support her spiky lyrics directed at the cold-hearted: “You’re so consumed with how much you get/you waste your time with hate and regret.”
16. ‘Holiday’ (1983)
An energetic bop with the sole purpose of promoting relaxation. What’s not to appreciate?
15. ‘Where’s the Party?’ (1986)
The combination of unfiltered joy on the dance floor and a gentle caution to slow down and enjoy the moment finds Madonna having fun, but also realizing, “I guess I’m one of the grownups, now I have to get the job done.” Yeah, been there.
14. ‘You’ll See’ (1995)
The dramatic opening – castanets, plucked guitar and an ominous palpitation – hints at Madonna’s courage as she prepares to methodically unleash one of her deepest statements on independence. Co-written with David Foster, the stately ballad is unwavering in its convictions.
13. ‘Lucky Star’ (1983)
With a cascade of synth notes and a glistening melody, Madonna continued her introduction to the world. Sliding in a reference to the nursery rhyme “Star Light, Star Bright” suggests that Madonna – who, as the story goes, wrote the lyrics on a yellow legal pad and created the music on a Casiotone keyboard – already had some clever ideas tucked away.
12. ‘La Isla Bonita’ (1986)
The first Madonna track stocked with Latin influences was initially presented as an instrumental demo to Michael Jackson by Patrick Leonard. “Quincy (Jones) called me and said, ‘I want to do something like Sade for Michael,’” Leonard recounted to USA TODAY. Jackson rejected the song, Madonna scooped it up, added lyrics and it became her 11th Top 5 hit on the Billboard Hot 100.
11. ‘Music’ (2000)
The title song of her eighth studio album kicks off with a call to the dance floor (“Hey, Mr. DJ, put a record on…”). Over squiggles of guitar and a thick funk backbone, Madonna smears her electronically manipulated vocals over a simple, universal theme: Music makes the people come together.
10. ‘Borderline’ (1983)
The sweet and salty synth-pop hit marked her first Top 10 single in the U.S. Some say it hints at sex, but it’s really just twentysomething Madonna having to explain to a lover that this is the best they’re going to get, so if that isn’t good enough, then just get out of the way.
9. ‘Like a Virgin’ (1984)
For her second album, Madonna had to be bold. So why not roll around a gondola wearing a crucifix while singing about losing your virginity? That ought to get some attention. The breakout moment in her career came wrapped in springy keyboards, high-pitched vocals and a chorus forever ingrained in pop history.
8. ‘Into the Groove’ (1985)
When Madonna sings “at night, I lock the door so no one else can see,” it usually implies something other than dancing. But this infectious bauble, featured in Madonna’s film debut, “Desperately Seeking Susan,” has no ulterior motive other than to assure the wallflowers that it’s OK to feel the beat.
7. ‘Like a Prayer’ (1989)
Despite the pearl-clutching reaction to its stigma-bashing video, Madonna’s boundary-breaking song signified a directional shift with a more adult bent. Along with its liturgical-based lyrics, “Like a Prayer” is a hearty composition, with rock guitar and a gospel choir elevating her usual pop backdrop.
6. ‘Express Yourself’ (1989)
Continuing her march into adulthood, Madonna preaches empowerment in a most relatable manner over a bed of lightly funky electronic percussion. Acceptance and self-worth are the keys Madonna dangles, and besides, who likes satin sheets, anyway?
5. ‘Take a Bow’ (1994)
The “Bedtime Stories” single remains her most elegant song. Co-written and produced by Babyface, it glides with strings and pillow-y keyboards. As Madonna says goodbye to a paramour who took her for granted, she expresses rare vulnerability when she sings, “How was I to know you’d break my heart?”
4. ‘Ray of Light’ (1998)
A supernova of sound, the title track from Madonna’s seventh album establishes her new sonic interests: electronica, techno-pop and trip-hop. The relentless adrenaline and skittering rhythm knitted into her first Top 5 debut on the Billboard Hot 100 is still a little piece of heaven.
3. ‘Papa Don’t Preach’ (1986)
Forget, for a moment, about the hullabaloo that accompanied the song’s debut on MTV. Sure, the unwed pregnant teen of the lyrics was keeping her baby, but gasp, the shame of it all. Madonna cannily managed to offend pro-abortion and anti-abortion advocates simultaneously, all while strolling through a bouncy pop song introduced by a sweeping string section.
2. ‘Vogue’ (1990)
Has there been a non-novelty dance anthem that has endured as a cultural touchstone, dance move and simply fantastic song? With a melody as sleek as Madonna’s pantsuits, “Vogue” captivated. And that spoken word section reeling off names from Hollywood’s Golden Age (Greta Garbo, Marlon Brando, Marilyn Monroe)? Considering Beyoncé pays homage to it on “Break My Soul” more than 30 years later speaks to its agelessness.
1. ‘Open Your Heart’ (1986)
Thrumming with an undercurrent of desire, Madonna’s fifth No. 1 single underscores her ability to sew snippets of innuendo so mischievously into the fabric of her work that you often don’t realize the true aim of a song. Couple that with a blissful shuffle beat and frisky keyboards and the result is a glorious confection with bite.
