To be clear: we’re dealing with one of few popular music catalogues where a top 100 songs list can shortchange an artist. These are the 100 songs that stand out the most to us, the ones we play over and over. Many of them make us want to dance, some make us cry, some are really funny, and some are quite sexy. They all remind us why the undisputed Queen of Pop is one of the most untouchable recording artists ever. In ascending order, these are our picks for the 100 best Madonna songs of all time. 100. “Bitch I’m Madonna” (Rebel Heart, 2015) This EDM track has swagger for days (not to mention a great title). The house-party music video features appearances from, among others, Beyoncé, Katy Perry, Miley Cyrus, Kanye West, Chris Rock, Rita Ora, Nicki Minaj and Diplo, but the best part is the adorable chorus of boys–dressed in vintage Madonna duds–that opens it. 99. “Impressive Instant” (Music, 2000) The aptly named Music era is perhaps Madonna at her most confident as a musician. Following the enormous acclaim and popularity of Ray of Light, Music feels like she just walked into the studio and trusted her instincts. Case in point: this bizarre, trance-inducing electronic symphony. 98. “Devil Wouldn’t Recognize You” (Hard Candy, 2008) Madonna explores betrayal and heartbreak in this mysterious, even ominous Hard Candy highlight. It closes the albumalong with another strong track, “Voices.” 97. “I Love New York” (Confessions on a Dance Floor, 2005) Rhyming “New York” with “dork” isn’t exactly delicate, but this is one of Madonna’s funniest tracks ever. It’s hilarious, actually. 96. “God Control” (Madame X, 2019) On this six-minute banger, Madonna delivers a message with an inspired, violin-heavy retro disco sound. The video became her most controversial and headline-grabbing in a minute. 95. “Nobody Knows Me” (American Life, 2003) A vortex of electronic blips and beeps swarms around Madonna as she informs us she doesn’t waste her time or watch TV. She performed this spectacularly on her Re-Invention Tour–with little in the way of theatrics, but seemingly boundless energy. 94. “You’ll See” (Something to Remember, 1995) One of the biggest reasons fans adore Madonna is that she shows considerable strength and resilience, and she’s not afraid to show her emotions. On this cinematic ballad, which tells of the end of a love affair, she reminds us that it takes strength to cry. 93. “Little Star” (Ray of Light, 1998) “Little Star” is a touching lullaby and love song dedicated to Madonna’s daughter, Lourdes Leon. She was born less than two years before the release of Ray of Light. 92. “Who’s That Girl” (Who’s That Girl, 1987) The title track from Madonna’s 1987 movie was her sixth Billboard number one. The song undeniably has its charms (the Latin accents are lovely), but it doesn’t hold up as well as some of her mightier songs of the era like “La Isla Bonita” or “Open Your Heart.” 91. “Love Profusion” (American Life, 2003) This blend of electronica and folk was co-written with frequent collaborator Mirwais Ahmadzaï. It was the fourth and final single from American Life, and the music video was directed by Luc Besson (The Fifth Element). 90. " I Want You" (Something to Remember, 1995) Collaborating with British trip hop group Massive Attack, Madonna took on the challenge of covering Marvin Gaye–and fully delivered. She was later in the running to sing one of Massive Attack’s most famous tracks, “Teardrop” (that became the theme to TV drama House). 89. “Waiting” (Erotica, 1992) Erotica is filled with some of Madonna’s most biting, delicious lyrics. This track ends with one of her best one-liners, which isn’t quite fit to print here. 88. “Swim” (Ray of Light, 1998) A sea change in Madonna’s spiritual life and trajectory is expressed in a song that actually features sounds of the sea. 87. “She’s Not Me” (Hard Candy, 2008) Madonna performed this Pharrell-produced, 70’s-sounding number on her Sticky & Sweet Tour (her highest-grossing tour ever) opposite dancers dressed in her iconic looks from the past. Later, she brought it back on the MDNA Tour in an apparent dig at Lady Gaga (they were feuding in code at the time). The two superstars have publicly buried the hatchet since. That was wonderful news–and such a relief–because we adore them both. 86. “Get Together” (Confessions on a Dance Floor, 2005) Co-produced by Stuart Price, the sonically soothing, Grammy-nominated second track of all-dance Confessions is tender and romantic. 85. “American Life” (American Life, 2003) It’s taken a while for critics and many fans to warm to this partially-rapped piece of fiery introspection, but Madonna has remained steadfast in her affinity for it. When she performed it at WorldPride 2019 (very unexpectedly), it took on a punk-rock new life, a whole new dimension. 84. “Falling Free” (MDNA, 2012) Madonna’s singing is disarmingly beautiful on this overlooked, sad and thoughtful closer to divorce album MDNA. 83. “Where’s the Party” (True Blue, 1986) This peppy synthesizer track is sometimes forgotten amidst the bigger hits, but it’s an essential Madonna track: a PSA reminding us that we all need to just have a good time every now and then. 82. “Unapologetic Bitch” (Rebel Heart, 2015) Diplo lays down the dancehall beats while Madonna lays down the law in this hilarious, enchantingly vulgar, reggae breakup jam. The artist did a prop-comedy routine with a banana during this song on her Rebel Heart tour, targeting many celebrities in the audience including Amy Schumer, Ariana Grande, Katy Perry and Idris Elba. 81. “Causing a Commotion” (Who’s That Girl, 1987) Critics were somewhat mixed on this one in 1987, but it’s remained popular with fans. Contrasting with the bubbly, upbeat sound, the lyrics were inspired by Madonna’s tumultuous relationship with then-husband Sean Penn (and some less-than-pleasant run-ins with the paparazzi). 80. “Love Don’t Live Here Anymore” (Something to Remember, 1995) First released on Like a Virgin, the best way to hear this Rose Royce cover is through the more tasteful remix of the official music video, released over a decade later. 79. “Nothing Fails” (American Life, 2003) American Life is an uneven record, but it has long stretches of brilliance. Maybe the album’s freshest surprise is when a gospel choir appears on this acoustic love song. 78.“Dear Jessie” (Like a Prayer, 1989) A big part of what makes Like a Prayer perhaps Madonna’s best album is the way she tackles different styles of music successfully.“Dear Jessie” is a children’s lullaby inspired by the daughter of co-producer Patrick Leonard (named Jessie). Leonard helped to create several of Madonna’s most unforgettable songs. 77. “Body Shop” (Rebel Heart, 2015) With a nod to the spirit of her earliest songs and an unusual, experimental, percussion-rich sound,“Body Shop” is so pleasing to the ears it’s easy to accept the lyrics are 100 percent metaphor comparing sex to auto repair. 76. “Bad Girl” (Erotica, 1992) This Shep Pettibone co-production tells a sophisticated story about a tragic figure. Madonna gives one of her best performances in the downbeat David Fincher-directed video, as a broken, unhappy woman who winds up getting killed. A characteristically graceful, tap-dancing Christopher Walken plays her guardian angel. 75. “Till Death Do Us Part” (Like a Prayer, 1989) Madonna’s rocky marriage and nullified divorce from Penn is dramatized in this inventive, emotion-filled Leonard collaboration. 74. “Crazy” (Madame X, 2019) One of the highlights of Madame X is this English/Portugese, accordion-heavy gem. Madonna sings about not letting her feelings get the best of her, and the idiomatic, multilingual wordplay is great. 73. “Jump” (Confessions on a Dance Floor, 2005) On the final single from Confessions, Madonna echoes Pet ShopBoys, sings about the possibilities of finding new love, and appears to reflect upon the move to NYC she made as a teen. There’s an upbeat, inspiring message here for some who might need it. The music video was shot in Tokyo and features some impressive parkour. 72. “Gang Bang” (MDNA, 2012) Here, Madonna creates a vintage grindhouse exploitation revenge flick within a tune. The vividly cinematic track builds and builds until she’s screaming at the end. It’s a lot of fun. 71. “To Have and Not to Hold” (Ray of Light, 1998) Subtlety is the key to this appropriately chilly number about a surface-level relationship that’s running on autopilot. 70. “Another Suitcase in Another Hall” (Evita, 1996) “Don’t Cry For Me, Argentina” is more well-known, but this is the best track from Evita’s score. Madonna embodied this role, giving an affecting performance that won her a Best Actress (Musical or Comedy) Golden Globe. 69. “True Blue” (True Blue, 1986) Madonna wrote this doo-wop valentine for then-new beau Penn. She most recently performed “True Blue” on her Rebel Heart Tour. 68. “Sooner or Later” (I’m Breathless, 1990) Theatre legend Stephen Sondheim wrote this slinky 1930s nightclub-style track used in the blockbuster Dick Tracy. Madonna upstaged absolutely everybody at the 1991 Oscars. Michael Jackson was her date, and she paid homage to Marilyn Monroe when performing “Sooner or Later,” which won Best Original Song. Other Dick Tracy song highlights include “More” and “Hanky Panky,” the notorious ditty about spanking. 67. “Spotlight” (You Can Dance, 1987) This dance track from Madonna’s first remix album sounds dated in a way several of her tracks from around this time do not. But for many, that surely just adds character and appeal–and the song is wildly successful in its mission to make us want to get up and shake it. 66. “Bye Bye Baby” (Erotica, 1992) Erotica is not a cuddly album and “this is not a love song.” Bye Bye Baby taunts and plays mind games. It’s far removed from Madonna’s more radio-friendly offerings, but it hurts so good. Cover song “Fever” is another stellar Erotica track that just barely missed this list. 65. “Keep It Together” (Like a Prayer, 1989) The stability and support we get from family is a topic Madonna has revisited throughout her career. This is her quintessential song about it, memorably performed in the style of Bob Fosse on her Blond Ambition Tour. 64. “I’ll Remember” (With Honors, 1994) Sweet, tearjerking ballad “I’ll Remember” marked a change in image for Madonna, whose 1992 Erotica was upstaged by negative press surrounding her Sex book and the critical bomb Body of Evidence. 63. “Miles Away” (Hard Candy, 2008) “Miles Away” tells of marital struggles, but it goes down easy–pleasantly even–thanks to easily recognizable production from Justin Timberlake and Timbaland. 62. “Love Spent” (MDNA, 2012) Definitely one of Madonna’s most underrated tracks, and the high point of MDNA. She lets it rip here; sounding heartbroken and furious as she belts about finances and lost love. An inspired bit of banjo opens the track, then by the end it’s synths turned up to 11. 61. “Sorry” (Confessions on a Dance Floor, 2005) Confessions on a Dance Floor might be the Madonna album with the most inexhaustible replay value, and “Sorry” is one of its highlights. It’s a thumping, witty kiss-off set in a ’70s roller disco. 60. “Something to Remember” (I’m Breathless, 1990) Madonna’s way with a ballad has long been underrated; a whole collection of her best was released under this title in 1995. “Something to Remember” is a perfect listen for a reflective rainy day. 59. “Celebration” (Celebration, 2009) This fetching and fun throwback was the title track from Madonna’s 2009 greatest hits collection. It’s perhaps best enjoyed in the Benny Benassi remix of the official music video. 58. “I Deserve It” (Music, 2000) This acoustic ballad with splashes of hip-hop was written for Madonna’s husband-to-be Guy Ritchie. They were wed in Dec. 2000 in the Scottish Highlands. 57. “Angel” (Like a Virgin, 1984) Often overshadowed by the more iconic tracks on her sophomore album, Angel remains a favorite with many dedicated fans, and it recently spiked in popularity thanks to the third season of Stranger Things. Co-producer Stephen Bray (who worked on several of Madonna’s hugest hits) won a 2017 Grammy for his revival of The Color Purple on Broadway. 56. “4 Minutes” (Hard Candy, 2008) The only gripe here is that Madonna kind of sounds like a featured artist on her own track opposite Timbaland and Justin Timberlake, but it’s mostly just big, brass-heavy, fun. 4 Minutes juggles myriad hooks with grace, and delivers a message about social awareness. It peaked at number two on the Billboard Hot 100, and is Madonna’s best-selling digital single ever. 55. “Beautiful Stranger” (Austin Powers: The Spy Who Shagged Me, 1999) This retro psychedelic track (with production that calls to mind The Doors, The Beatles and more) earned Madonna her fifth Grammy (Best Song Written for Visual Media). The instrumentation is similar to that of “Amazing” on Music; both songs are brilliant on their own terms. 54. “Paradise (Not For Me)” (Music, 2000) Madonna tackles a lot of heavy subject matter in this Mirwais collaboration: grief, the past, and even suicide. A stripped-down “Paradise” was an unexpected addition to her Confessions Tour. 53. “Die Another Day” (American Life, 2003) This Golden Globe and Grammy-nominated song is the title track from the 20th James Bond movie of the same name. Electroclash seemed like an odd fit for Bond at the time, but Madonna sells the hell out of it. Her music video generates more excitement than the campy Bond film. 52. “Over and Over” (Like a Virgin, 1984) “Over and over” is so catchy, with a hook that hits you–well–over and over–that it’s hard to believe it wasn’t released as a single. Madonna went on to create more sophisticated soundscapes, but “Over and Over” is a shining example of the raw materials she’s had since the beginning. 51. “Mer Girl” (Ray of Light, 1998) Madonna revisits the theme of Like a Prayer’s “Promise to Try” (the traumatic loss of her mother) with even more tact on Ray of Light’s closer. It’s an atmospheric song about death that is–fittingly–unsettling. 50. “Medellín” (Madame X, 2019) Madge and Colombian mega-hottie Maluma’s sultry, symmetrical game of cat-and-mouse is more pleasurable with every spin. Their riveting performance at the 2019 BBMAs was the highlight of the night. Featured artists on Madonna records don’t always work (who could possibly match her for personality?), but she confects pure ear candy with Maluma; there’s genuine, easy chemistry there. 49. “Future Lovers” (Confessions on a Dance Floor, 2005) “Connect to the sky/Future lovers ride/Their ambitions high/Would you like to try?” is a breathtaking chorus. 48. “Rain” (Erotica, 1992) A Shep Pettibone co-production, perhaps the warmest track on “Erotica” is a ballad that blends trip hop and new-age sounds in a harmony-rich soundscape you just want to get lost in. 47. “Drowned World/Substitute for Love” (Ray of Light, 1998) The first track of Madonna’s radical record immerses you in her state of mind; she’s craving authentic connection and searching for sincerity. The imagery of the music video sparked some outcry as it echoed the scene of the paparazzi chase that led to Princess Diana’s death a year earlier. 46.“In This Life” (From Erotica, 1992) Madonna eulogizes loved ones lost to the AIDS epidemic in this ballad that samples George Gershwin’s “Prelude No. 2 for Piano.” This subject is also the basis of Like a Prayer’s “Spanish Eyes,” which possesses a similar raw lump-in-the-throat power. 45. “Oh Father” (Like a Prayer, 1989) “Oh Father” is the biggest tearjerker from Like a Prayer. One of several visually stunning collaborations with director Fincher, the video was Madonna’s most autobiographical clip up to that point, maybe ever. “Oh Father” sees an adult Madonna finding grace with her estranged dad. 44.“Nothing Really Matters” (Ray of Light, 1998) Madonna says the discovery of unconditional love (courtesy of her young daughter) was the inspiration for this Ray of Light single. 43. “Sanctuary” and “Bedtime Story” (Bedtime Stories, 1994) We’re tying these because they’re bridged together on the album, creating an arresting experience that’s unlike anything else in Madonna canon. Bedtime Stories, like Erotica, is one of Madonna’s best and most underrated records. It ends in spectacular fashion. The techno poetry of “Sanctuary” leads into the brain-frying “Bedtime Story” (co-penned by Björk), then the record closes with “Take a Bow.” 42. “This Used to Be My Playground” (standalone single, 1992) The theme to A League of Their Own was Madonna’s tenth Billboard number one, breaking a record previously held by Whitney Houston as female artist with the most chart-toppers. The lyrics are wistful and poetic. 41. “Like It Or Not” (Confessions on a Dance Floor, 2005) The chorus here is fairly simple, but delivered with Madonna’s conviction it’s downright life-affirming. It also lends itself beautifully to LGBTQ Pride. 40. “The Power of Good-Bye” (Ray of Light, 1998) You can like it or not, You can love me or leave me, ‘Cuz I’m never gonna stop." Sweeping ballad “The Power of Good-Bye” is about empowerment and freedom that’s on the other side of a tough breakup. The aqua-tinted, steamy music video (featuring a way-hunky E.R.-era Goran Višnjic) is so impossibly pleasing to the eyes it makes a lot of designer perfume commercials look slapdash. 39. “Give It 2 Me” (Hard Candy, 2008) Here’s a helpful tip: If you ever need an extra boost of energy near the end of a strenuous workout, this thing works like a charm. Add it to your cardio playlist if it’s not on there already. 38. “Think of Me” (Madonna, 1983) Madonna has recorded dozens of songs that are more artistically adroit than “Think of Me,” but the star power she exudes on it is a formidable sign of things to come. 37. “Ghosttown” (Rebel Heart, 2015) The second-best track on Rebel Heart is one of Madonna’s best-ever ballads, envisioning a romance at the end of the world. Terrence Howard and Madonna make a captivating couple in the video, both showcasing some razor-sharp dance moves. 36. “Sky Fits Heaven” (Ray of Light, 1998) This mystic and invigorating Ray of Light track conjures up some ethereal lyrics. 35. “Physical Attraction” (Madonna, 1983) “Physical Attraction” is classic old-school Madonna. The only reservations are that the lyrics aren’t as clever as the best tracks on the debut album, and listening to it today, it’s easy to appreciate how much better her voice got over time. 34. “Gone” (Music, 2000) Music’s closer is one of Madonna’s most haunting and naked moments. Acoustic and seemingly unguarded, she sings about survival, fame and her very unconventional life. 33. “Burning Up” (Madonna, 1983) One of Madonna’s punkest moments has starker production than other songs of the era. This thing rocks particularly hard when Madonna plays the electric guitar live (as seen on her Reinvention and Rebel Heart tours). 32. “Crazy For You” (Vision Quest, 1985) A slow-dance staple for decades now, Madonna’s second Billboard Hot 100 number one was recorded for the soundtrack of cult classic coming-of-age movie Vision Quest starring Matthew Modine. “Gambler” was another popular track recorded for the film. 31. “Dress You Up” (Like a Virgin, 1984) The infectious, mildly risqué final single from Like A Virgin reached number five on the Billboard Hot 100. The single release’s B-Side was “Shoo-Bee-Doo.” 30. “La Isla Bonita” (True Blue, 1986) This Spanish lullaby is one of Madonna’s favorites to perform on tour. A young, way-pre-Oscar Benicio del Toro can be seen in the background of the video, which was a widely requested smash on MTV. 29. “Take a Bow” (Bedtime Stories, 1994) This collaboration with Babyface and others features a full orchestra, and it’s about the sting of unrequited love. When Take a Bow became Madonna’s 11th number-one Billboard single (where it stayed for seven weeks), she surpassed Carole King as the female artist with the most songs to hit the top spot. The influential, matador-themed video is one of Madonna’s best. 28. “Don’t Tell Me” (Music, 2000) Madonna’s defiant, rebellious personality that we love is on full-blast in this extremely clever and infectious song. In the sparse, innovative video, she revolutionized cowboy chic. 27. “Erotica” (Erotica, 1992) Though it was underrated in its time (overshadowed by the release of Madonna’s coffee table book and Body of Evidence), these days the jazzy, dark Erotica stands tall as one of the best, most daring pop LPs of the 1990s, its influence undeniable in the work of artists like Beyoncé, Rihanna, P!nk, Britney Spears, Lady Gaga, Christina Aguilera, Years & Years, Ariana Grande, Katy Perry, Nicki Minaj and more. 26. “Living For Love” (Rebel Heart, 2015) Oh, what a joy it was for fans in 2015, when more than three decades into her career, The Queen of Pop dropped one of her best tracks ever. The lead single from Rebel Heart is a triumph about perseverance and keeping an open heart, even if it’s been broken. The production is a marriage of gospel choir and a deep EDM beat only Madonna could pull off, with Alicia Keys on percussion and piano. 25. “Papa Don’t Preach” (True Blue, 1986) Madonna’s fourth No. 1 U.S. single was controversial for its depiction of teen pregnancy. Not only does the song tackle a complicated subject with humanity and the gravity it merits, it’s got an aces pop hook driving it. The video was directed by James Foley, who directed Penn in At Close Range. 24. “Everybody” (Madonna, 1983) Madonna’s debut single still holds up like gangbusters, an irresistible invitation to party. She most recently performed it on select stops of her 2015 Rebel Heart Tour. 23. “Deeper and Deeper” (Erotica, 1992) A killer flamenco guitar solo is the secret sauce on this triumph of a disco banger. This is the first Madonna track where she referenced her own “Vogue.” The music video paid homage to Andy Warhol. 22.“Frozen” (Ray of Light, 1998) This expansive, melancholy electronica ballad was the first single from Ray of Light, announcing the singer’s radical new sound. The lyrics explore the emptiness one feels when unwilling to connect and be vulnerable. Preach. 21. “Justify My Love” (The Immaculate Collection, 1990) It’s a sign of this mega-star’s eminence that a single used to promote her first greatest hits collection is now considered a signature track. This steamy hotel party was too hot for MTV, becoming Madonna’s first video banned on the network. She used this to her advantage, selling the video as a single on VHS (the first music video ever sold in this format). It was a runaway success. These days, the Justify My Love video honestly looks fairly tame—not to mention tastefully, artfully photographed.
- “Cherish” (Like a Prayer, 1989) This doo-wop Patrick Leonard collab stands tall as one of the most uplifting pop songs ever, exuberant yet deeply romantic. It peaked at No. 2 on the Billboard Hot 100, making Madonna the artist with the most consecutive top five hits in history. Herb Ritts shot the famous merman-heavy music video in Malibu.
19. “Secret” (Bedtime Stories, 1994) A mystery box of a song that pulls you into its gravitational pull completely upon every listen, “Secret” was the lead single of Bedtime Stories. Madonna adapted the look of classic Hollywood sex symbol Jean Harlow for the black-and-white music video. 18. “Rescue Me” (The Immaculate Collection, 1990) “Justify My Love” was the more popular Immaculate addition, but “Rescue Me” is arguably even greater. Madonna is a towering life force here. She is rumored to perform “Rescue Me” live for the first time ever on her upcoming Madame X Tour. Fingers crossed! 17. “Secret Garden” (Erotica, 1992) So intimate and personal it feels invasive, acid jazz number “Secret Garden” is Erotica’s best track. Madonna sings and speaks about sex, resilience, love, and the possibility of motherhood over strings and winds. 16. “What It Feels Like For a Girl” (Music, 2000) Lyrically barbed but sonically soft, one of Madonna’s most radical tracks explores the brutality of being a woman in a man’s world. The clip, directed by then-husband Ritchie, contains violent and disturbing content. It was banned from airing on MTV—even though more violent clips by male artists, like Eminem‘s “Stan,” were deemed OK. Though it was recorded nearly two decades before the #MeToo movement, this track feels like an anthem for it. Madonna was, and is, ahead of her time. 15. “Material Girl” (Like a Virgin, 1984) Though it played an indispensable part in her becoming a household name, Madonna has, at times, expressed regrets over recording this track, because she doesn’t like being referred to as “Material Girl.” On her most recent tour she performed a rousing mimicry of the music video (itself a pastiche of Marilyn Monroe’s “Diamonds are a Girl’s Best Friend” from Gentlemen Prefer Blondes). The video and the song have only been referenced and parodied about a billion times in pop culture. Among the best recreations: Nicole Kidman’s showstopper in Moulin Rouge! and “Cereal Girl” from Sesame Street. 14. “Lucky Star” (Madonna, 1983) Co-produced by Reggie Lucas and Madonna’s then-boyfriend John “Jellybean” Benitez, “Lucky Star” began Madonna’s unprecedented string of 16 consecutive top five hits. She sported her her signature bangles, rosaries and exposed midriff in the video; it’s perhaps the moment she became a style trendsetter. 13. “Human Nature” (Bedtime Stories, 1994) Madonna tells the haters to take a hike in this mesmerizing, funny and angry R&B earworm.“Human Nature” is always spirited and flat-out amazing whenever Madonna performs it live (she does often); that’s one reason it’s so high on this list. 12. “Open Your Heart” (True Blue, 1986) An essential Madonna cut was actually intended for Cyndi Lauper in its nascence. No list of Madonna’s best music videos is complete without this hilarious, lightly controversial clip. Many analysts even say this is the defining moment she subverted the male gaze. 11. “Music” (Music, 2000) Madonna’s first track of the new millennium had the daunting task of living up to Ray of Light, the biggest success of her career. She didn’t disappoint in the slightest. The funky, club-ready Music is one of Madonna’s signature anthems: it’s all about the way music unites us. The video is a hip-hop party, filled with comedy, animation and gender-swapping (Madonna plays a pimp), co-starring Sacha Baron Cohen as notorious white rapper Ali G. 10. “Hung Up” (Confessions on a Dance Floor, 2005) Madonna reached out to ABBA for permission to sample “Gimme! Gimme! Gimme! (A Man After Midnight)," and the Swedish pop group gave her a rare yes. “Hung Up” was Madonna’s 36th top 10 single on the Billboard Hot 100, tying her with ElvisPresley as the artist with the most ever (she later broke the record with “4 Minutes.” “Hung Up,” and the John Travolta-inspired video that accompanied it, will entertain you into submission. 9. “Like a Virgin” (Like a Virgin, 1984) Madonna’s first Billboard number one, the title track from her sophomore LP, is the moment she went from being a big star to being an icon. She often plays it on tour, experimenting with world music instrumentation to freshen it up. This always ends up reinforcing just how clever and skillfully constructed this song is. 8. “Into the Groove” (Desperately Seeking Susan, 1985) Pure unbridled joy. Two things inspired a young Madonna to co-write this sweetly innocent, endlessly catchy classic: her love of dance, and her infatuation with a beautiful Latin boy in her NYC neighborhood. Legend. 7. “Holiday” (Madonna, 1983) Many say this is where it all began. Madonna’s first mainstream hit was the third single from her eponymous debut album. The Queen of Pop most recently performed “Holiday” as a victory-lap encore on her masterful Rebel Heart Tour, dressed as an American flag. 6. “Borderline” (Madonna, 1984) A timeless, yearning love song we can never hear too many times. Madonna most recently performed this (in fine vocal form) on The Tonight Show withJimmy Fallon. 5. “Ray of Light” (Ray of Light, 1998) Madonna underwent extensive training in preparation for the lead role in 1996’s Evita, and this is her best vocal ever. The song has been covered dozens of times by artists all over the map. One of the best is Natasha Bedingfield‘s stunner from 2007. She noted how difficult the song is to sing. The Jonas Åkerlund-directed music video cleaned house at the VMAs. 4. “Express Yourself” (Like a Prayer, 1989) This anthem of empowerment is Madonna at her most soulful (“Come on, girls! Do you believe in love?”), and the Fincher-directed video, inspired by Fritz Lang‘s silent sci-fi masterwork Metropolis, is a massively-scaled tale of oppression, freedom and control. 3. “Live to Tell” (True Blue, 1986) This is universally regarded as Madonna’s finest, most emotional ballad… and these just might be her strongest-ever lyrics. It’s not every day you hear a pop star weave themes like childhood instabilities, traumas and fears into a number one Billboard pop hit. That’s what happened here. 2. “Like a Prayer” (Like a Prayer, 1989) Gospel, pop, and classic rock come together to create a masterwork that silenced those who doubted Madonna’s talent. Directed by Mary Lambert, the music video featured provocative imagery that stirred up controversy. The clip also delivers a vital message about civil rights, it’s moving and exhilarating, and it’s a serious contender for best music video of all time. 1. “Vogue” (I’m Breathless, 1990) “Vogue” tops our list because it’s possible this is the song in all of Madonna’s incomparable catalogue that’s had the greatest cultural impact. “Vogue” ruled the airwaves in every corner of Earth in the summer of 1990, and it’s still a hot topic right now (thanks in part to FX’s acclaimed series Pose). A Pettibone co-production, “Vogue” brought an underground movement into the mainstream; winking to (and even name-checking) the past while creating something cutting-edge. It’s also very possible that “Vogue” is the ultimate LGBTQ Pride Month anthem. This is a song about unity. What’s your favorite Madonna track? Think we missed one? Sound off in the comments!
