When Prince died five years ago this week, he left behind one of the richest, deepest, smartest, funniest, most beautiful and most complicated collections of work that pop music has ever known.
And it hasn't stopped growing since he passed.
Prince believed in sprawl, as he demonstrated with double and triple albums and with an internet storehouse of music he invited his fans to wander. Since his death, the artist's estate has issued multiple LPs and box sets of material pulled from the famous vault at his Paisley Park complex in suburban Minneapolis.
Yet Prince was also devoted to the concise pleasures — and to the market-exciting potential — of a hit single. In his career as a solo act and as the frontman of the Revolution and the New Power Generation, he placed 47 songs on Billboard's Hot 100, all of them before digital streaming opened up pop's flagship chart to viral flukes.
To celebrate his flair for the short form, we've ranked every one of Prince's singles, from worst to best, in the list below. Using information from Prince's official website, Discogs and the exhaustingly detailed PrinceVault.com, our list seeks to include the A-side of every single Prince released commercially in the U.S. between his 1978 major-label debut, "For You," and his death, from an accidental overdose of Fentanyl, at age 57 on April 21, 2016.
The list omits remixes, rerecordings and songs he wrote and produced for other acts, though it reflects some editorial judgment in including several promo-only releases that attained obvious single-hood through music videos, TV commercials and the like.
Three of Prince's longtime collaborators — engineers Susan Rogers and David Z and guitarist Dez Dickerson — shared their thoughts on a number of songs as well.
85. "Hardrocklover" (2015)
A character sketch of a woman who prefers hard rock to "Sade and Babyface" — set against an overwrought electro-metal arrangement that fails to explain why.
84. "The Arms of Orion" (1989)
From the "Batman" soundtrack, one of Prince's gloopiest ballads, with the singer in the role of Bruce Wayne and Sheena Easton as Vicki Vale.
83. "Peach" (1993)
Fuzzy blues guitar + looped Kim Basinger moan = something new to entice folks to pay for "The Hits/The B-Sides."
82. "The Song of the Heart" (2006)
Prince's interest in animated penguins + the kids movie "Happy Feet" = an opportunity to write a Golden Globe-winning theme song.
81. "Pretzelbodylogic" (2014)
Noodling by numbers.
80. "Damn U" (1992)
Swank but forgettable.
79. "Purple Medley" (1995)
Just what it says: a tightly edited mega-mix of some of Prince's biggest hits.
78. "Free Urself" (2015)
The last single Prince released before his death … sounds an awful lot like MGMT's "Kids"?
77. "Supercute" (2001)
Plenty of musicians have written admiring songs about exotic dancers; fewer have written them from the perspective Prince takes in this sly workplace drama: "Maybe it's 'cause she come from East LA/ But every time I see her body on display/ I gotta call her name from the DJ booth."
76. "Pink Cashmere" (1993)
A middling melody gussied up with fancy film-score strings.
75. "Insatiable" (1991)
In which Prince teaches someone named Martha how to make a sex tape.
74. "This Could B Us" (2015)
A so-so electro-funk jam based on a meme based on a scene from "Purple Rain."
73. "New Power Generation" (1990)
Prince introduces his new backing band with a promise to keep "pumping the big noise in the '90s."
72. "The Truth" (1997)
A stinging acoustic blues that might be the most stripped-down single he ever made.
71. "S.S.T." (2005)
A warm, Bill Withers-ish soul-folk tune released as a fundraiser for victims of Hurricane Katrina.
70. "Glam Slam" (1988)
Not much of a tune, but any history of late-'80s shoegaze should make room for what Prince was doing here on guitar.
69. "I Wish U Heaven" (1988)
68. "Thieves in the Temple" (1990)
At the box office, Prince's "Purple Rain" sequel "Graffiti Bridge" made a fraction of what its predecessor did. But the soundtrack still spun off a top 10 hit with its vaguely mystical lead single.
67. "Space" (1994)
Prince goes trip-hop.
66. "Te Amo Corazon" (2005)
Prince goes smooth jazz.
65. "Betcha By Golly Wow!" (1996)
An exceedingly faithful cover of the Stylistics' early-'70s soul classic from 1996's triple-CD "Emancipation," which also featured a respectful take on the Delfonics' late-'60s "La-La Means I Love You."
64. "Days of Wild" (2002)
Lengthy live rendition of a rowdy funk-rap cut from 1998's "Crystal Ball," with cleaned-up language to suit Prince's becoming a Jehovah's Witness around the turn of the millennium.
63. "Fixurlifeup" (2013)
Key lyric from Prince's fuzzed-out first single with the all-woman power trio 3rdEyeGirl: "Girl with a guitar is 12 times better than another crazy band of boys."
62. "Partyman" (1989)
On vocals, Prince as the Joker; on bass, Prince as Bootsy Collins.
61. "Scandalous!" (1989)
Another "Batman" cut, this one a synth-smeared ballad for which Prince's father is credited as co-writer.
60. "Cinnamon Girl" (2004)
The title cribs that of Neil Young's late-'60s proto-grunge classic (just as Lana Del Rey's "Cinnamon Girl" did in 2019). But the tune feels more like Prince's stab at "Beggars Banquet"-era Rolling Stones.
59. "Just As Long As We're Together" (1978)
Speedy, breathy, super-detailed disco-funk in which Prince can't decide which instrumental skill he wants to show off first.
58. "Let's Work" (1982)
Inspired by a local Minneapolis dance craze (and originally titled "Let's Rock"), "Let's Work" "is all about the groove," says Dez Dickerson, who played guitar in the earliest lineup of the Revolution. "We called it 'the pocket.' Hours and hours and hours were spent locking that down. And if you couldn't get in the pocket and stay in it, you weren't gonna be in Prince's band very long."
57. "Take Me With U" (1985)
A lightly trippy psych-soul duet between Prince and Apollonia that feels like the bridge between "Purple Rain" and "Around the World in a Day."
56. "F.U.N.K." (2007)
55. "Breakdown" (2014)
A moving pop-stardom-is-hard plaint in which Prince reflects on his youthful overindulgence ("First one intoxicated, last one to leave/ Waking up in places that you would never believe") as well as his iffy real estate decisions ("I used to want the house with the biggest pool/ Reminiscing now I just feel like a fool").
54. "America" (1985)
"Prince was oddly conservative — very much a Minnesota boy," says Susan Rogers, the singer's trusted engineer throughout the mid-'80s who now teaches at Boston's Berklee College of Music. "And he could be kind of a scold. He'd stand there and wave his finger and say, 'You shouldn't behave like this.'" In this propulsive Reagan-era funk track with worries about a creeping communist threat, Prince is "issuing a warning," Rogers adds. "He's saying we all better start paying close attention."
53. "Dance 4 Me" (2009)
Recycling the iconic drum-machine beat from "When Doves Cry," Prince addresses a "funky congregation" in this highlight from the throwback-minded "MPLSound," which he sold exclusively at Target.
52. "Screwdriver" (2013)
A blistering garage-soul rave-up about life on the road, which he defines adorably as "sharing stories in cool clothes."
51. "Letitgo" (1994)
Perhaps the sultriest song ever recorded about an artist's disagreement with his label's release strategy.
50. "Extraloveable" (2011)
A vintage early-'80s lyric — "Whenever you need someone to take a shower with, call me up, please" — retrieved from the vault and given sparkling new life.
49. "Rock and Roll Love Affair" (2012)
"She believed in fairy tales and princes"; he believed in a swinging horn section.
48. "Musicology" (2004)
"Don't you hear this old-school joint?" Prince growls near the end, by which point you certainly have. To David Z's ears, the Grammy-winning "Musicology" combines the lessons Prince learned from James Brown, Sly Stone, Jimi Hendrix and Mick Jagger. "That's who he was studying on his way up — their moves and their licks," says Z, who worked with Prince in his earliest studio sessions. "The guy did nothing but practice."
47. "Still Waiting" (1980)
Another obvious source of wisdom: Smokey Robinson.
46. "The Work Pt. 1" (2001)
But mostly James Brown.
45. "The Greatest Romance Ever Sold" (1999)
"Tell me that's not a hit," Prince dared a New York Times reporter as he showed off a preview of this deliciously slinky slow jam — to which the universe responded: "Can do." Though it deserved better, "Greatest Romance" stalled out at No. 63 on the Hot 100.
44. "Fallinlove2nite" (2014)
First heard as part of Prince's appearance on an episode of the Zooey Deschanel sitcom "New Girl" (!?), here's an endearingly tender Europop jam that rhymes "Underneath the taffeta" with "If I see the moon, I'll just laugh at her."
43. "The Holy River" (1997)
A shimmering pop-rock gem (complete with blazing guitar solo) that Prince released in typically quirky fashion as a cassette single available only at Borders stores.
42. "U Make My Sun Shine" (2000)
How did Prince repay the compliment that was D'Angelo's "Untitled (How Does It Feel)"? By recruiting D's ex, Angie Stone, for a creamy R&B duet that made clear his sound wasn't yet up for grabs.
41. "Gold" (1995)
More turf-guarding in this cranky yet lush arena-rock ballad: "Everybody wants to sell what's already been sold," he complains amid piping synth-strings. "What's the use of money if you ain't gonna break the mold?"
40. "Guitar" (2007)
Prince monetized this knowing hard-rock exercise — "I love you, baby/ But not like I love my guitar" — by letting Verizon put it in cellphone commercials. Song still stomps.
39. "Why You Wanna Treat Me So Bad?" (1980)
The lyric is directed toward an insensitive lover, but Prince likely had other thoughts in mind when he chose this uptempo number to finish the second of two famously disastrous performances in which he was pelted with bottles as he opened for the Rolling Stones at LA's Memorial Coliseum in 1981.
38. "Breakfast Can Wait" (2013)
A nod to Dave Chappelle's viral sketch about Prince making pancakes (R.I.P. Charlie Murphy), this sleek R&B flirtation features some of the singer's funniest line readings.
37. "Batdance" (1989)
One indication of the pop-cult mania surrounding Tim Burton's "Batman" reboot? The fact that this hard-edged and nearly tuneless theme song went to No. 1. Today, "Batdance's" extensive sampling feels endearingly primitive, which might be why Rogers' Berklee students "didn't respond to it at all" when she played it for them recently.
36. "Eye Hate U" (1995)
Carmen Electra has said that Prince told her she inspired this jilted lover's lament, which climaxes with a thrillingly perverse courtroom sequence in which the singer asks the judge to let him and the defendant reenact "how good it used to be" right there on the witness stand.
35. "The Morning Papers" (1993)
A lovely, intricate soul-rock power ballad that charts the beginning of Prince's May-December romance with his first wife, Mayte Garcia.
34. "Money Don't Matter 2 Night" (1992)
How best to present Prince's thoughts on wealth inequality (as illustrated in a stirring music video directed by Spike Lee)? How about a silky jazz-pop arrangement a la Steely Dan?
33. "Alphabet St." (1988)
"Cat, we need you to rap," Prince tells Cat Glover, and boy does she ever in a tongue-twisting verse about kissing your enemies like you know you should and jerking your body like a horny pony would.
32. "Sexy M.F." (1992)
A James Brown-ish boast both as tight and as louche as can be.
31. "Mountains" (1986)
Wendy Melvoin and Lisa Coleman of the Revolution came up with "Mountains'" perpetual motion machine of a groove, but it's Prince's airy falsetto — which Rogers is pretty sure they recorded with a "cheap little stage mike" at Prince's rehearsal warehouse — that gives the song its blissed-out energy.
30. "Do Me, Baby" (1982)
From the otherwise jittery "Controversy" album, a beautifully laid-back outlier of an old-school R&B love song.
29. "Anotherloverholenyohead" (1986)
This funky "Parade" cut rides one of the great Prince bass lines. But it opens with a squirmy, theremin-like solo played on a Roland synth-guitar that Rogers remembers as "a real pain in the neck." "It didn't track very well," she says of the instrument. "You'd move your hands on it and it wouldn't necessarily give you the pitch that corresponded to the position of your hands. We brought it on tour, but it was just so unreliable that Prince had to scrub the whole thing and come up with a different arrangement for doing it live."
28. "My Name Is Prince" (1992)
A year later his name actually wasn't Prince but an unpronounceable symbol. Here, though, over a throbbing breakbeat clearly inspired by hip-hop, he delights in the way the word pops — just one more percussive element in a track full of them.
27. "Gett Off" (1991)
"Twenty-three positions in a one-night stand" is Prince's ambitious goal in this exceptionally raunchy new jack swing number, which he somehow made hornier still when he performed "Gett Off" — the singer's first official release with the New Power Generation — in a pair of bottomless yellow trousers at 1991's MTV Video Music Awards.
26. "Soft and Wet" (1978)
David Z remembers hearing Prince's debut single for the first time. "I was a little bit shocked," he says of "Soft and Wet's" highly suggestive lyric. "That's not something that anybody around Minneapolis was doing at all. Or anybody anywhere, really. Whatever Tipper Gore was objecting to, he started it."
25. "Let's Pretend We're Married" (1983)
"Whatever you heard about me is true," Prince admits-slash-brags in this jumpy new wave anthem, which is one way to resolve the contradictions of a guy who says he's "in love with God" mere seconds after telling his bride-to-be, "I sincerely wanna f— the taste out of your mouth."
24. "7" (1992)
The spiritual messaging is famously hard to parse in this sitar-enhanced tune that mentions streets of gold, 12 souls and a river of blood. But anyone doubting that Prince was heeding some kind of numerological inspiration should recall that "7" somehow peaked … at No. 7.
23. "Dirty Mind" (1980)
Prince's third album opened with a lean, angular title track that announced straightaway he'd retooled his sound for a new decade.
22. "Cream" (1991)
Clearly unsatisfied by the Power Station's 1985 remake of "Get It On," Prince swipes T. Rex's classic blues-glam lick for his own ode to doing it, this one with added orgasm sounds and some sinuous slide guitar. "Cream" became the fifth of Prince's five No. 1 pop hits.
21. "Uptown" (1980)
Titled after a neighborhood where Prince and his pals hung out, "Uptown" describes a kind of racial utopia where "white, black, Puerto Rican — everybody just a-freakin'." But if Minneapolis in the early '80s didn't quite live up to that ideal — "For sure he took some artistic license," says Dickerson — Prince's band wasn't the only one in town with members from various walks of life. "A lot of the local groups were multiracial," Dickerson says. "Might be a Black frontman with a primarily white group, or Hispanic guys and white guys and Black guys all in the same band. That was always there."
20. "Delirious" (1983)
Like the chord progression with its '50s-era rock 'n' roll vibe, the car metaphor in Prince's lyric starts off innocent enough. By the third verse, though, he's asking for "a little ride up and down/ In and out and around your lake." Chuck Berry would approve.
19. "Controversy" (1981)
What's brilliant about Prince's response to the moral outcry triggered by the previous year's "Dirty Mind" is how un-shook he sounds in this light-as-a-feather robo-rock jam. "People call me rude," he sniffs, "I wish we all were nude."
18. "Pop Life" (1985)
Slap bass never sounded better (nor Prince more bitter) than in this account of the disillusioning experience of success.
17. "Baltimore" (2015)
Prince wrote his last top-shelf single in the immediate aftermath of Freddie Gray's killing by Baltimore police. "Enough is enough, it's time for love," he pleads — yet this determined protest song also reminds those in power, "If there ain't no justice then there ain't no peace."
16. "U Got the Look" (1987)
This crisp pop-rock come-on was originally much slower, according to Rogers, who says that after hours of work, Prince wiped everything but the drum track, sped up the beat on a tape machine, then began building the song again at its new tempo. "I think one of the reasons we stuck with it — we spent days on it, which was unusual for him — is that he knew he needed something kind of optimistic," Rogers says, for the comparatively downbeat "Sign o' the Times." The result, featuring a panting vocal turn by Sheena Easton, went to No. 2 on the Hot 100.
15. "I Could Never Take the Place of Your Man" (1987)
"Sign's" other straightforward pop tune followed "U Got the Look" up the chart to No. 10 but laid out a more complicated emotional scenario, with Prince gently assuring a woman in a bar that he's not the guy to help her get over a bad breakup.
14. "Raspberry Beret" (1985)
The image is easy to grasp: a beautiful woman wearing a fancy hat (and, when it was warm, not much more). But the music, with strings and harpsichord over a clip-clop beat, defies classification even now.
13. "Diamonds and Pearls" (1991)
Between the bawdy extremes he was exploring in "Gett Off" and "Sexy M.F.," a plush and stately love song with a star vocal turn by the NPG's Rosie Gaines.
12. "The Most Beautiful Girl in the World" (1994)
Frustratingly, it's missing from most streaming services thanks to a legal entanglement stemming from one of the many short-lived record deals Prince struck after his epic battle with Warner Bros. But the final top 10 hit of his life is a gorgeous '70s-soul-style number well worth the trip to a used CD shop (or, uh, YouTube).
11. "Black Sweat" (2006)
Twenty years after "Kiss," Prince showed he could still make a banger with just a few elements (and just a few jokes).
10. "I Wanna Be Your Lover" (1979)
Prince's first brush with greatness, which grew out of his crush on Patrice Rushen, is an ecstatic post-disco classic whose radio-ready hooks deliver a characteristically risky proposition: "I wanna be your brother/ I wanna be your mother and your sister too."
9. "1999" (1982)
"I was dreaming when I wrote this," Lisa Coleman sings at the top, before Prince takes over to describe a nightmarish vision of nuclear annihilation. Yet "1999" ranks among the singer's most infectious party songs — and not because he doesn't think the end is really coming.
8. "I Would Die 4 U" (1984)
Over a thrumming beat that starts out of nowhere and seems like it could go on forever, Prince drops what might be the heaviest opening lines in '80s pop: "I'm not a woman/ I'm not a man/ I am something that you'll never understand."
7. "Little Red Corvette" (1983)
"It changed everything," Dickerson says of the song that ushered Prince and the Revolution into the top 10. "It was a hit everywhere and with everybody; all of a sudden we were on MTV all the time." Michael Jackson had been the "battering ram" for Black artists on the cable network, Dickerson says, "and we came in right behind."
6. "When Doves Cry" (1984)
When Prince topped the Hot 100 for the first time, he didn't do it by sanding the unruly edges from his music; he did it with his weirdest song to date: a stark psychosexual drama, famously without a bass line, that's also about his difficult relationship with his parents.
5. "Let's Go Crazy" (1984)
Every sound in "Let's Go Crazy," which reached No. 1 less than two months after "When Doves Cry" left the top spot, seems to push the song upward until Prince's guitar explodes like a Roman candle.
4. "Sign o' the Times" (1987)
Inspired in part by the bad news he saw splashed across the front page of the Los Angeles Times one summer day in 1986, the title track of Prince's magnum opus addresses AIDS and the crack epidemic in language as haunted and unsparing as the song's rigorously pared-down groove.
3. "Purple Rain" (1984)
The foundation of Prince's signature ballad was caught on tape during a gig in 1983 at Minneapolis' First Avenue club, where David Z watched with worry from behind a mobile recording rig as people in the audience "just stood there" in front of the stage. "I was like, 'Why aren't they moving?" Z recalls. "Then I realized they didn't know the song. He was playing it for the first time." More likely is that they were simply stunned by the intensity of Prince's singing and guitar playing, which he somehow came close to equaling on the countless nights he went on to play "Purple Rain" after it became a live staple. In 2007 he closed his Super Bowl halftime show with a mind-blowing rendition that "kind of brought people back to Prince," Z says. "He wasn't exactly on top of the world at that point. Music had gotten kind of formulaic. But he proved that everything is bulls— except for talent."
2. "Kiss" (1986)
Prince famously took back this minimalist-funk masterpiece for himself after writing it for Mazarati, a band formed by the Revolution's keyboardist, BrownMark. According to Z, who'd produced the Mazarati version, Prince didn't add much: just a few guitar licks copped from James Brown's "Papa's Got a Brand New Bag" and a new lead vocal. "But of course Prince's vocal makes the whole thing," Z says with a laugh, and indeed "Kiss" showcases the singer's one-of-a-kind battery of grunts, coos and yowls. Which didn't mean it was an easy sell with Prince's label. "'Kiss' was the first song we turned in off 'Parade,'" Z recalls, "and the Warner Bros. A&R guy said, 'We're not putting that out — it's got no bass, it's got no reverb, it doesn't sound like anything else. Prince really f— up." The label eventually relented, and the song spent two weeks at No. 1 before winning a Grammy Award.
1. "If I Was Your Girlfriend" (1987)
The concept alone is an all-time pop achievement: What intimacies do women share with one other outside the heteronormative framework that most pop songs serve to reinforce? Yet it's the deeply caring (and un-male-gaze-y) way that Prince moves through that question — and in a pitch-shifted voice that further resists old-fashioned gender binaries — that marks "Girlfriend" as a work of genius. Who else would have thought to make a song like this? Who else could have pulled it off?
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