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The 25 best Prince songs of all time

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MINNEAPOLIS (WCCO) -- Bob Dylan may have won the Nobel Prize, but Prince will forever remain Minnesota's foremost musical superstar, and it's not even close.

Wednesday marks what would have been Prince's 65th birthday, even though, for many fans, he will be "forever in their lives."

In honor of the music that formed the sonic core of the famed "Minneapolis sound," here are our picks for the 25 best Prince songs ever.

We've imposed a totally arbitrary three-per-album song limit because, let's be honest, it was the only way we could prevent Purple Rain from locking down nine of the available slots here. In roughly chronological order:


"I Wanna Be Your Lover" (Prince, 1979)

Prince broke the bank (well, comparatively speaking) on his debut album, and as such was forced to strip things down and get extra efficient for his sophomore effort. No problem at all for an already preternaturally prolific talent like Prince. His self-titled debut featured at least two songs he intended to be performed by his then-musical crush Patrice Rushen (of "Forget Me Nots" fame), but it's hard to imagine anyone other than Prince selling this, his first significant hit song. Coy, teasing, and somehow still very bashful, it remains a tantalizing early taste of what was to come.

"Dirty Mind" (Dirty Mind, 1980)

Well that bashful thing sure didn't last long. Having notched a modicum of crossover credibility under his belt, Prince immediately decided to remove it (his belt) entirely, stripping away all R&B sheen in favor of spare, New Wave grit, and getting altogether too hot for radio (well, Top 40 radio anyway). But the critics went gaga for the raw, unfiltered id of Dirty Mind; it landed him his first-ever spot on the Village Voice's venerable Pazz & Jop critics' poll. Ironically, the far more overtly rock-oriented effort made Prince an even bigger star on R&B charts, and the insistently pounding title track instantly became his new mission statement.

"Sexuality" (Controversy, 1981)

As much punk as they were R&B, Dirty Mind's rough demos rewrote the playbook he perfected with his next album, Controversy. "Sexuality" wasn't among the LP's hit singles, but in its drive, it's the album's speed-freaky high point -- fast, furious, funktastic. "I'm talking about a revolution, we gotta organize/We don't need no segregation, we don't need no race/New age revelation, I think we got a case." With "Sexuality," Prince moved from mission statement to full-blown manifesto.

"Do Me, Baby" (Controversy, 1981)

It took him a few years, but with "Do Me, Baby," Prince finally landed his first insta-classic slow jam. And, in its full-length seven-minute album version, Prince declared he was in no mood to rush the mood. To think that he was only four years and four albums into his career and already capable of turning an entire nation on.

"Nasty Girl," Vanity 6 (Vanity 6, 1982)

By this point, the songs were pouring out of Prince at a truly terrifying clip. Side projects began to spring from every corner of his purple universe. And, in some cases, he got away with even more explicit fantasies when he voiced them through his proliferating protégés. The trio of Vanity 6 leave less than nothing to the imagination while asking, one presumes ironically, "Do you think I'm a nasty girl?" Whatever would've given us that idea?

Vanity 6 - Nasty Girl (1982) • TopPop by TopPop on YouTube

"1999" (1999, 1982)

With the propulsive title track of 1999, Prince managed to make a decisive move toward the mainstream without sacrificing any of the harder edges that made him a critics' darling, specifically in the song's boldly apocalyptic lyrical content. And he assured himself relevance 17 years later. Oh, and it was one of the foremost hit singles that assured the world that dance music, post-disco, wouldn't be dying anytime soon, thank you.

"Something in the Water Does Not Compute" (1999, 1982)

There aren't many genres that Prince didn't try on for size, invariably leaving them forever changed in his wake. Somehow, Prince's 1999 also contained what has to be considered one of the very earliest examples of the Detroit techno style even before that genre's most prominent practitioners were in the game. "Something in the Water Does Not Compute" is a sleek, metallic, unyielding sonic experiment, capped off by Prince's untamed vocal acrobatics, all in service of conveying a libido forever thwarted.

"How Come U Don't Call Me Anymore" (B-side of "1999" single, 1982)

Few if any pop superstars amassed a collection of B-sides as rich, varied and flat-out great as Prince did. "How Come U Don't Call Me Anymore" -- with its hard, percussive piano accents, bluesy chord progressions, and reverberatingly lonely vocal performance -- was but the first of them majestic enough to stand shoulder with any of his other A-side classics.

"When Doves Cry" (Purple Rain, 1984)

It's hard to imagine that this track, which has as strong a claim as any other track to being considered Prince's be-all, end-all signature song (it's his highest ranking at the aggregation site Acclaimed Music), was actually cooked up at the very last minute as a last-minute swap for the project that would soon become Prince's own personal supernova: Purple Rain. From its gothic flourishes, to the fact that it's a dance track without so much as a bassline, little more remains to be said about "When Doves Cry," but plenty more remains to be heard.

"The Beautiful Ones" (Purple Rain, 1984)

"Baby, baby, bayyyy ... bee!" If you put Prince's microphone-gun to my head and asked us to name Prince's single best vocal performance ... well, let's just say you wouldn't even have to put a microphone-gun to our head. "The Beautiful Ones" always wins, each and every time. In its five galvanizing minutes, Prince glides from playful tremulousness to soul-cleansing shrieks with a pit stop everywhere in between. The lyrics are knowingly picturesque (as in "paint a perfect picture"), but Prince's vocals are startling and direct.

"I Would Die 4 U" (Purple Rain, 1984)

Messianic much? The absolute hubris of "I Would Die 4 U," which, alongside its companion piece "Baby I'm a Star," brings the film version of Purple Rain to its triumphant climax, would have seemed altogether too much. For those not baptized in the waters of Lake Minnetonka, it might still be. But for those of us wholly caught up in the sweep of Purple Rain, the pulsing, synth-driving omniscience of "I Would Die 4 U" is a verification of Prince's crowning moment.

"Erotic City" (B-side of "Let's Go Crazy" single, 1984)

A minor cheat as this is also from the landmark Purple Rain set (pushing the whole package's song tally here to four), but given the song itself may (or may not) have broken a few FCC rules when radio stations started spinning it, despite the arguable presence of a certain four-letter word, we're willing to break our three-per-album rule too. The B-side to "Let's Go Crazy," Prince's down 'n' dirty album-opening funk jam, is plenty suggestive lyrically, but even more obscene sonically.

"I Feel For You," Chaka Khan (I Feel For You, 1984)

This 1979 song (another intended for Patrice Rushen) achieved its full fame thanks to R&B belter Chaka Khan's characteristically guttural take on it five years later, complete with Stevie Wonder harmonica solo and a deathless opening rap from Grandmaster Melle Mel. ("Chaka Khan, let me rock you, let me rock you, Chaka Khan!") Khan's version may very well be the greatest pop single of the '80s, but I also reserve a special fondness for Prince's original, slower disco version, no more so than when he turned it into his own little girl group tribute on the Musicology tour.

"4 the Tears in Your Eyes" (We Are The World, 1985)

The King of Kings has long been a supporting character in Prince's discography. His relationship with Jesus Christ is, obviously, complex and multi-faceted, but that's what makes it so compelling. The one early case where Prince doesn't seem conflicted at all is this song, his contribution to the USA for Africa LP We Are The World. Far from wrestling with his hedonistic impulses, Prince presents a simple parable: "The meek shall inherit the earth." Prince can make you believe anything.

Prince & The Revolution - 4 The Tears In Your Eyes (35th Anniversary Edition) HQ by The Jacksons Music on YouTube

"Pop Life" (Around the World in a Day, 1985)

Prince wisely chose to follow up his massive 1984 by focusing on the psychedelic minutiae of his sound, not the meat and potatoes stadium rock. "Raspberry Beret" was the major pop crossover hit that reassured the world, but it was the album's minor hit that I hold dear. Those varispeed piano riffs, the swirling strings, the snarky two-liners ("What's that underneath your hair? Is there anybody living there?). "Pop Life" is a rarity in Prince's catalogue: a totally underrated hit single.

"She's Always in My Hair" (B-side of "Raspberry Beret" single, 1985)

If you were to ask the hardest-of-hardcore Prince fans which of his B-sides reigned above all others, you'd likely get the strongest support behind "She's Always in My Hair," a wry, witty take on the joys and doubts of romantic attachment, and the eternal struggle between domestic bliss and private torment, all playing out beautifully against one of the hardest synth riffs Prince ever wrote.

"Sometimes It Snows in April" (Parade, 1986)

You don't have to be a Minnesotan for this delicate lament to be your favorite Prince ballad, but it sure doesn't hurt.

"If I Was Your Girlfriend" (Sign O' the Times, 1987)

Sexuality and gender roles are as much Prince's bread and butter as murder mysteries were Alfred Hitchcock's. Most of the time, it's pretty clear where Prince's first-person and second-person pronouns fall, but for "If I Was Your Girlfriend." Undoubtedly one of the very strangest in his string of alien pop singles, Prince adopts his "Camille" alternate persona to sing to a potential romantic conquest of all the fun things he could do with her if only he was her girlfriend. Or is he singing as a woman to a man about wishing she could make him happy? Or is it a man pretending to be a woman singing to a woman about wanting the total intimacy that can only come from same-sex pairings? All of the above, as far as we're concerned. The unresolvable sexual confusion of "Girlfriend" is endlessly worth unpacking for subtext.

"Adore" (Sign O' the Times, 1987)

Sign O' the Times is Prince's grandest, most freewheeling effort, and very likely his overall best album. For much of its 80 minutes, it's a wild, slippery, uncontainable work of free-associative genius, with each successive song (from "Housequake" to "The Ballad of Dorothy Parker" to "Starfish and Coffee" to "It") seemingly inventing its own new genre from the ground up. So it comes as a breath of fresh air when it all culminates in the still-odd but otherwise reassuringly grounded "Adore," a Quiet Storm-tinged love ballad that still retains Prince's wicked twist of humor.

"Nothing Compares 2 U," Sinead O'Connor (I Do Not Want What I Haven't Got, 1990)

Prince has written many female vocalists' most indelible songs. Not just Chaka Khan, but Sheila E. ("The Glamorous Life"), Vanity ("Nasty Girl"), Apollonia ("Sex Shooter"), and The Bangles ("Manic Monday"). But no other singer ever managed to take a Prince song and so fully make it her own as did Sinead O'Connor with "Nothing Compares 2 U." Originally written for side project The Family, the song was all but ignored until O'Connor tore through the opening salvo ("It's been seven hours and 15 days since you took your love away") against producer Nellee Hooper's spare piano-and-drum backdrop. The result is unforgettable.

"The Question of U" (Graffiti Bridge, 1990)

The movie Graffiti Bridge very, very much failed to repeat the alchemy that made Purple Rain a hit six years prior. And, admittedly, the movie's soundtrack lacks the cohesion and momentum that kept its antecedent's LP at #1 on the Billboard charts for 24 solid weeks (longer than any other album since, aside from Adele's 21, which achieved the same feat). But amid Graffiti Bridge's bloat are more than a couple hidden gems, including two idiosyncratic ballads that have endured despite the project's overall reputation -- the sultry story-song "Joy in Repetition," and the near-mystic, mutant blues dirge of "The Question of U," possibly the most unusual song of any of these cited 25.

"Money Don't Matter 2 Night" (Diamonds and Pearls, 1991)

If "The Question of U" is this list's strangest song, then "Money Don't Matter 2 Night," from Prince's almost capitulatory-commercial Diamonds and Pearls LP, is unquestionably his most smoothly mainstream. For some, that might render it too negligible for consideration among his best. For others, it only proves just how mutable his genius truly was that he could knock out a Teflon-smooth pop ditty as vanilla as "Money" clearly is, and yet still stand out amid the Top 40 din.

"I Hate U" (The Gold Experience, 1995)

If "If I Was Your Girlfriend" testified to the myriad joys the difference of the sexes can feed into intimacy, "I Hate U" is the tormented flipside. The delivery is definitely cruder, but so is the message: "It's so sad that I hate you, 'cause you're all that's ever on my mind." And if the lyrics don't sell you on Prince's irritation, the howling guitar solo that closes the song will remove any doubt.

"Sleep Around" (Emancipation, 1996)

The cliche goes that, within any double- or triple- or quadruple-album is a 45-minute masterpiece struggling to emerge. With Emancipation, Prince's celebratory end-zone dance at finally emerging from out of his contract with Warner Bros. Records, the sheer glut of the material on display is the entire point. The glow of his long-deferred glee in independence frequently transcends the bloat, but if there's a single moment that radiates in his joy over total artistic freedom, it's "Sleep Around," a four-on-the-floor disco-house stomp very much in the vein of analog-era Masters at Work. Need more proof? Check out his irrepressible smile performing the track on Oprah.

"Call My Name" (Musicology, 2004)

Doing a list like this, it's difficult not to feel like one's giving the short shrift to the latter half of Prince's discography, even as the sheer brilliance of his fruitful first decade makes it an impossible inevitability. The regal dignity of "Call My Name," the sort of mature love ballad that could only come from the other side of Joni Mitchell's proverbial both-sides-now cloud, ensures that no list of Prince's best need be strictly pre-1999.


Apologies to some of the heavy-hitters left off the list like "Kiss" and "Raspberry Beret," the die-hard Prince fan favorites like "When You Were Mine," "Joy in Repetition," and "17 Days," and some of the other major Prince-written sidebars like The Time's "The Bird," Tevin Campbell's "Round and Round," and Paula Abdul's "U" -- to say nothing of the many, many unreleased tracks and outtakes from the vault, like "The Line," "G-Spot," and his immortal, heavily bootlegged Small Club cover of "Just My Imagination."

With that, here's the full playlist of 25 songs all in one spot. Happy birthday, Prince!

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