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Madonna at 60: Queen of Pop’s 60 best singles ranked

Mayer Nissim August 15, 2018

Few artists in pop history have had the longevity or carefree eclecticism of Madonna.

As the undisputed Queen of Pop turns 60 on August 16, here at PinkNews we celebrate her remarkable career by ranking her top 60 singles, from all the way back in 1982 to the present day.

60. “American Life” (2003, from American Life)

After the critical acclaim of Music, Madonna took a leftwards step for American Life and its self-reflective title track and lead single sums up everything right and wrong with the album at the same time.

Grasping for a hook but not quite reaching it. Wilfully experimental but still chasing the game.

59. “Hanky Panky” (1990, from I’m Breathless)

Years before Fifty Shades of Grey (and her own Erotica), Madonna released this strangely sexless ode to S&M riffing off a bit in Dick Tracy (“I don’t want you to thank me / You can just spank me”). It’s every bit as daft as it sounds but the jazzy, swing keeps it bouncing along nicely.

58. ‘Spotlight” (1988, from You Can Dance)

A True Blue reject from the writers of “Holiday,” “Spotlight” snuck onto remix album You Can Dance and fit in quite nicely. A bigger hook would have nudged it up these rankings, but there’s still plenty to like in this Sly and the Family Stone-inspired dancefloor shuffle.

57. “Living for Love” (2014, from Rebel Heart)

Undermined by leaks and a laughable promo campaign and muddled by an overload of producers, Rebel Heart limped out apologetically, but there were still flashes of genius because, bitch, she’s Madonna. Opener “Living For Love” mixed up that classic Madonna ’80s sound with just enough verve and R&B bounce to feel relevant.

56. “Drowned World/Substitute for Love” (1997, from Ray of Light)

The fourth single and opener of Ray of Light, this is probably Madonna’s most understated, subtle single of the lot. On first listen not much happens, but if you give it time it slowly unravels and floats right through you.

55. “Dear Jessie” (1989, from Like A Prayer)

A psychedelic, experimental kiddy lullaby for co-writer Patrick Leonard’s daughter, this umpeenth single from Like A Prayer is one of the most un-Madonna like singles she ever released and maybe one of the most disarming and charming.

54. “4 Minutes” (2008, from Hard Candy) [featuring Justin Timberlake and Timbaland]

While some of her later collaborations ended up a clattering mess, this hook-up with Justin Timberlake and Timbaland is a solid, funky bit of dance-pop, albeit one that sounds more like a JT/Timbaland song featuring Madonna than the other way around.

53. “Miles Away” (2008, from Hard Candy)

Madonna returned to the acoustic twang parts of Music and American Life singles for this Hard Candy cut but the vibrant drum loops, and genuine emotion as she treads over her long-distance marriage with Guy Ritchie elevate it.

52. “Give Me All Your Luvin'” (2012, from MDNA) [featuring MIA and Nicki Minaj]

Nestling among all the limp Zeitgeist-chasing, cynical hookups and “drugs are mad eh” embarrassment was this pure pop gem of a collaboration. Nicki Minaj and MIA combine with one of Madonna’s catchiest hooks in years for a giddy victory of fun over finesse.

51. “Don’t Cry For Me Argentina” (1997, from Evita)

Madonna’s movie career has ranged from the ridiculous (Body of Evidence, Die Another Day) to the sublime (A League of Their Own, Desperately Seeking Susan), but Alan Parker’s Evita is probably the highlight. Not too proud to take singing lessons to get that musical opera style, this song capped off her award-winning performance.

50. “Get Together” (2005, from Confessions on a Dance Floor)

After a few years away from the disco Madonna hooked up with Stuart Price for what was her most unambiguously danceable album. Borrowing the vibe from Stardust’s megasmash “Music Sounds Better Than You,” this track underlined her return to the club.

49. “Gambler” (1985, from Vision Quest)

This Jellybean-produced track from the Vision Quest soundtrack has all-but disappeared… you’ll struggle to find it in the shops (or on Spotify), which is a shame. Entirely self-penned, this thrashy-clashy post-punk pop racket clatters through with a gauche of-its-time charm.

48. “Crazy For You” (1985, from Vision Quest)

The other Vision Quest single and one that shrugged off its origins more easily, “Crazy For You” was a rare early bit of floaty balladry and likely proved a point to all those who had dismissed Madonna as gloss and glamour without any sort of range.

47. “Love Don’t Live Here Anymore” (1996, from Something to Remember)

Madonna originally covered this Rose Royce classic for the Like A Virgin album before reworking it for her Something To Remember ballads collection with extra pomp and verve. A rangey and brave choice, she pulls it off with seeming ease.

46. “Keep It Together” (1990, from Like A Prayer)

A groovy funked-up tribute to Sly and the Family Stone and Sister Sledge that pays homage to Madonna’s family and the importance of keeping it all together (“Don’t forget that your family is gold”), advice she didn’t quite take herself as the years unfolded.

45. “Causing a Commotion” (1987, from Who’s That Girl)

From the Who’s That Girl soundtrack Madonna hooked up with the True Blue dream team of Patrick Leonard and Stephen Bray, and this hepped up strut inspired by her tumultuous relationship with Sean Penn was one of the highlights, taking the opportunity for a nod to her own “Into The Groove.”

44. “Rescue Me” (1991, from The Immaculate Collection)

Tacked on to Madonna’s first (and incredibly-titled) best of, “Rescue Me” comes off a little like a rehash of the more-polished “Vogue,” but when you’re riffing on a song that good then you’ll still come up with something pretty special.

43. “Don’t Tell Me” (2000, from Music)

When Madonna gets fusion right, she gets it really right. This mashup of country folk and electronica with stop-start rhythms and cut-up lyrics really shouldn’t work but it absolutely does.

42. “Take a Bow” (1994, from Bedtime Stories)

A stately, grandiose, string-laden hit about those dying burning embers as a relationship fades away. Babyface and Nellee Hooper combine for a gentle, if emotional bit of Radio 2-friendly heartstring-tugging.

41. “Me Against The Music” (2003, from In The Zone) [featuring Britney Spears]

Madonna’s first proper duet single (she’s ramped those up in recent years with varying success) and still her best, even if it’s technically a Britney single. Funked up modern pop R&B soundtracks the loan of the Queen of Pop crown, capped off with that taboo-smashing onstage kiss at the MTV VMAs.

40. “I’ll Remember” (1994, from With Honours)

After all the Sex (her coffee table book) and Erotica, Madonna took a sideways turn back nearer the middle of the road and this hooky bit of pop balladry dragged her back to the mainstream.

39. “Sorry” (2005, from Confessions on a Dance Floor)

Another classic Madonna breakup song where she takes absolutely no prisoners. A pure ‘70s disco stomper built on a throbbing Jackson 5 bassline. Yes, we can feel it and we feel suitably admonished (but still strutting).

38. “Music” (2000, from Music)

If you can ignore the back-of-a-fag-packet lyrics and cringey music video, the title track and lead single from Music is a quirky, gltchy, daft, delight, with Madonna and Mirwais stepping into the new millennium with an experimentally fun spirit.

37. “Burning Up” (1983, from Madonna)

Like “Everybody,” this early track still finds Madonna in that Factory/punk disco space, jittering her way to the pop charts via guitars that wouldn’t sound out of place on an early New Order or late Joy Division record.

36. “You’ll See” (1995, from Something To Remember)

A stunning Something To Remember ballad and one of the all-time great breakup songs (“You think that I can’t live without your love / You’ll see”). Singing well is the best revenge

35. “Everybody” (1982, from Madonna)

Where it all began. Before she became a pop queen and out-and-out superstar, Madonna’s spunky early work bounced off the post-punk discotheques everywhere from New York to Manchester and her Reggie Lucas-produced debut shows exactly why,

34. “Who’s That Girl” (1987, from Who’s That Girl)

On the back of “La Isla Bonita,” Madonna kept up the Latin vibe with more Spanish lyrics, this title track from the Who’s That Girl soundtrack offers up layers upon layers of synths, strings and vocals.

33. “Material Girl” (1985, from Like A Virgin)

Despite so many Madonna songs’ preoccupation with sex, god and love, she still gets called the Material Girl to this day. That’ll be the power of an irritating hook and scratchy, smartass vocals dripping with wry cynicism.

32. “True Blue” (1986, from True Blue)

An almost throwaway, retro romp, the title track of True Blue is an uncomplicated bit of devotion for Madonna’s then-husband Sean Penn. What it lacks in grit it makes up for in lightness and bounce.

31. “Nothing Really Matters” (1999, from Ray of Light)

An appropriately forward-focused, heavy-hitting dance track (“Nothing takes the past away / Like the future”) that underlined the Ray of Light ethos of leaving what’s done behind and opening your heart and mind.

30. “Oh Father” (1989, from Like A Prayer)

A haunting, autobiographical ballad wrestling with god, family and bereavement. Up there with John Lennon’s “Julia” and “Mother” as a heavy study of loss, but with an underlying feeling of strength and faith dragging its head above water.

29. “Open Your Heart” (1986, from True Blue)

Originally written for Cyndi Lauper, it ended up on Madonna’s desk and she gave it a rewrite and shakeup (and quite possibly added a bit more sly sexuality) for this love-as-sex, sex-as-love strut.

28. “Secret” (1994, from Bedtime Stories)

After the Erotica furore and pure romance balladry of “I’ll Remember,” Madonna inched tentatively back towards the bedroom with a newly-discovered green-eyed R&B vibe powered by collaborator Dallas Austin, and pulled it off magnificently.

27. “Borderline” (1984, from Madonna)

Slowing things down (a touch) for the final single from her debut, “Borderline” was the song that proved early on that Madonna was no one-trick disco show pony. Deep in themes and melody, she stretched her voice to aim for all the notes and hit ‘em too.

26. “Human Nature” (1995, from Bedtime Stories)

A riposte to the Erotica backlash finds Madonna mixing up her new R&B sound with that sexed-up vibe of her previous album. Sounding like Britney before Britney, Madonna gives her critics a deserved thrashing (“Oops, I didn’t know I couldn’t talk about sex”).

25. “Cherish” (1989, from Like A Prayer)

A retro, doo-woppy pop bounce, “Cherish” is one of the lighter moments of Like A Prayer but shows that Madonna could fling out single-after-single in the late 1980s that other artists would hang a whole career off.

24. “Celebration” (2009, from Celebration)

A sweetener for her third best-of compilation of the same name, “Celebration” finds Madonna going for her own post-Peaches/Calvin Harris trance pop banger, and for all its disposability, with dance icon Paul Oakenfold on production duties it just can’t be resisted.

23. “Ray of Light” (1998, from Ray of Light)

For all her dancehall history and disco dalliances, Madonna has never sounded as out-and-out techno as she does on “Ray of Light.” An insistent, pounding, wonderful headache of a song.

22. “Hollywood” (2003, from American Life)

A much more knowing and cynical look at La La Land than her earlier “Vogue,” Madonna pulls together the twangiest of guitars and the gltichiest FX for her best Mirwais collaboration and the clear highlight/saving grace of American Life.

21. “Hung Up” (2005, from Confessions on a Dance Floor)

Madonna had flirted with disco throughout her career but had never been quite so D.I.S.C.O. before. Built around a prominent ABBA sample but entirely it’s own thing, this joyous hookup with Stuart Price for Confessions… catapulted her back up the charts and in the critics’ good books.

20. “What It Feels Like For A Girl” (2001, from Music)

Hooked on a sample from Charlotte Gainsbourg’s death ‘n’ incest indie flick The Cement Garden, this isn’t the giddy girl power anthem you might expect but instead a sober, downbeat but vital deconstruction of society’s treatment of sex and gender.

19. “Deeper and Deeper” (1992, from Erotica)

A thumping, pumping, bassy fusion of Shep Pettibone-powered house and pop that’s equal parts disco and bedroom and still finds room for a cheeky lyrical and melodic nod to “Vogue” (“Let your body go with the flow”), What’s not to love?

18. “Dress You Up” (1985, from Like A Virgin)

An underrated slab of fashion frenzy, “Dress You Up” has all the polish of NIle Rodgers’s very best productions and a deceptively catchy chorus that sneaks up on you and gets in with a hammer blow

17. “Express Yourself” (1989, from Like A Prayer)

A melody so catchy Lady Gaga borrowed it for “Born This Way” a couple of decades later, “Express Yourself” was a pop empowerment anthem the first time we heard that tune. A riposte to her own “Material Girl,” it asks girls to urge their men to open their hearts, rather than their wallets, to prove their love.

16. “Lucky Star” (1983, from Madonna)

If “Holiday” was a statement of pop intent, “Lucky Star” underlined that statement in silver and gold glitter pen. The guitars are still there, but they’re high up the fret in jagged slices of irresistible disco funk that anticipates her future hook-up with Nile Rodgers.

15. “Live to Tell” (1986, from True Blue)

The lead single from True Blue, Madonna sidestepped the swirling controversy of “Like A Virgin” to come up with what’s probably still her best slowy. Its arrangement pulls at the heartstrings while Madonna’s voice stabs you deep.

14. “Beautiful Stranger” (1999, from Austin Powers: The Spy Who Shagged Me)

We long dreamed of Madonna doing a Bond theme and when it finally happened with “Die Another Day” the results were so disappointing it didn’t even make this list. No matter, this track from a Bond spoof sequel more than made up for it with sunny-side up breakup song that bounces.

13. “Bedtime Story” (1995, from Bedtime Stories)

Written by Björk (the sole collaboration between these pop queens), and my god, doesn’t it sound like it. This absolutely wouldn’t sound out of place on the the ex-Sugarcube’s Debut or Post albums, and with Madonna’s vocals it shouldn’t work but just does. An unlikely ambient dance pop classic.

12. “Justify My Love” (1990, from The Immaculate Collection)

Sure, Madonna sung plenty about sex plenty before “Justify My Love,” but she hadn’t really a song that actually sounded sexy. This changed all that, and kicked off a still-underrated sex-trip-hop era of music whose influence you can hear in damn near all pop today.

11. “Like A Virgin” (1984, from Like A Virgin)

After the success of her first clutch of singles, “Like A Virgin” took Madonna interstellar on wave of melody and controversy. About the emotional and physical impact of real love (not a “a guy with a big dick,” Quentin) and despite being written by two guys, “Like A Virgin” underlined Madonna’s complete artistic ownership of herself as a sexual being.

10. “La Isla Bonita” (1987, from True Blue)

Apparently first offered to Michael Jackson as an instrumental, the hazy, dizzy swirl of the ultimate holiday romance is perfectly captured in this Latin-infused groove carried by twangs of Spanish guitar.

9. “Rain” (1993, from Erotica)

The softest, most atmospheric (and least overtly sexual) bit of Erotica but no less sensual and seductive for it. Its shimmering, trippy Gaia vibe anticipated where Madonna would go a few years on with Ray of Light.

8. “Vogue” (1990, from I’m Breathless)

Not for the first time, Madonna dragged the underground into the overground, taking the pose-striking voguing craze from the dancehalls of Harlem to every single nightclub in the world. That spoken-word superstar worship would sound utterly ridiculous coming from anyone else but from Madonna is on-the-beat perfect.

7. “Frozen” (1998, from Ray of Light)

After the sidesteps of Something to Remember and Evita, Madonna came storming back in the late ‘90s with her first proper album for ages in Ray of Light, led by this remarkable single. William Orbit and Madonna join forces for an electronic pop wonder powered by motherhood and mysticism.

6. “Erotica” (1992, from Erotica)

Taking the baton from “Justify My Love” and not just running with it, but teasing the hell out of you with it while you’re all tied up. The scratchy, trip-hop loops and breathy vocals combine for some of most carefree, unpretentiously sexy music ever released.

5. “The Power of Good-Bye” (1998, from Ray of Light)

While “Frozen” was the more immediate choice for a stunning comeback, it’s “The Power of Good-Bye” that lingers as the most perfectly-formed electronic fusion of Madonna and William Orbit’s mysticism and melancholy.

4. “Like A Prayer” (1989, from Like A Prayer)

What could go wrong with an unambiguously devotional gospel pop song about a woman deeply in love with God? Well, the music video featuring a woman fleeing cross-burning racists and kissing a black saint riled up the usual suspects. An undisputed masterpiece and defining moment in pop.

3. “Papa Don’t Preach” (1986, from True Blue)

A rare example of Madonna-as-storyteller, with collaborator Brian Elliott coming up with an incredibly authentic bit of teen melodrama underpinned by a synthy hookfest. Unfairly dismissed (or claimed) as a pro-life anthem, its lyrics are much more personal, open and interesting than that.

2. “Holiday” (1983, from Madonna)

After the post-punk disco of her first two singles came Madonna’s first proper assault on the pop charts, as she handed over production duties to Jellybean and changed her life forever. While it didn’t leave her nightclub roots behind completely, it merged with pure pop melody and helium Little Eva vocals that effectively launched her career.

1. “Into the Groove” (1985, from Like A Virgin)

Madonna has probably sung more emotional, more danceable, more experimental and technically ‘better’ songs, but as a distillation of pure pop joy, “Into the Groove” more than earns its place as her very best single. An irresistible, multi-layered masterpiece that twists and turns and drags you along for every single, breathless beat.

More: Madonna, madonna 60th birthday, madonna at 60, madonna best songs

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