The 25 greatest Prince songs of all time

There are hit singles that redefine what you think you know about popular music. “I Wanna Hold Your Hand,” “Johnny B. Goode” and “(Sittin’ On) The Dock of the Bay” stand out in that regard. “Little Red Corvette” didn’t sound like anything Prince had recorded prior to “1999,” and bore little aural resemblance to the work of his major influences like James Brown and Sly & the Family Stone. It was a conjuring act of culture-shifting importance. There was only one person who could write that song. That’s genius.

In the film of the same name, “Purple Rain” is primarily the creation of Prince’s bandmates, Wendy & Lisa. For a proud, do-it-all Renaissance man like Prince, it’s a beautiful gesture to cede creative ownership in such a selfless manner. The song became an anthem; every time Prince performed live, there was the expectation that he’d haul out “Purple Rain.” He almost always obliged, but he wouldn’t linger on the closing guitar solo; he’d already given away his best interpretation of the song, and there was no topping that.

A downright filthy song backed up by a guitar solo that could very well be Prince’s finest hour wielding an axe. It’s lodged in the middle of “Graffiti Bridge,” an LP that most people didn’t buy upon release and even fewer revisit due to the lousy reputation of the film. This is a shame because Prince has never been more inspired.

Prince is a peerless storyteller, as evidenced by this surprisingly sensitive tale of a player informing a heartbroken young woman that he can’t be the man she’s looking for. It’s all conveyed over the course of a lively five-minute song that captures both the melancholy and the carelessness of the situation. There is a cut-down single version of this track that robs it of its loose, sprawling brilliance. Stick with the LP cut.

Prince was beginning to fade as a cultural influencer when this single struck like a lightning bolt out of nowhere in 1992. Once again, this is Prince running counter to the dominant sound of the day. New Jack Swing was dominating R&B, but this was straight-up, horn-heavy, James Brown-inspired funk. The song might’ve been one of the biggest hits of all time had the title been more radio-friendly; unfortunately, the edited version sacrificed the nasty charm of this swaggering masterpiece.

Dearly beloved, we are gathered here today to acknowledge that no one has ever torched a recording studio like Prince and the Revolution did the day they laid this rocker down. Prince’s wordplay is exquisite (“Pills and thrills and daffodils will kill”), and the Revolution steps up to the sonic task. It’s a musical narcotic — a controlled substance in 4/4 time.

“I used 2 cry 4 Tracy because I wanted to see him again/But sometimes … sometimes life ain’t always the way.” The final song of “Parade,” Prince left his fans with the perfect song through which they could mourn him. It’s just that no one expected that day to come so soon. It’s Prince’s loveliest, most delicate ballad and all the more effective due to its closing lyrics: “All good things they say never last/And love, it isn’t love until it's past.”

The ultimate B-side. “Erotic City” first appeared as a companion to the “Let’s Go Crazy” single in 1984. It resurfaced two years later in its full, extended form on the 12-inch release of “Girls & Boys.” It was a song with mystical powers. There were tales of radio stations being driven out of business by the FCC simply for playing the song on the air. Lyrically, it’s not as bad as its reputation suggests; its greatest offense is being remarkably frank. But it’s a stone groove, one of the greatest party songs ever.

A slamming, booty-shaker of a song. As Prince got on in years, he lost touch of his R&B following because his beats began to lose their snap. Some of this was due to the sterile production, but every now and then he’d unleash a single that could jam a dance floor like none other. “Gett Off” was a track with ill intent; any non-Jethro Tull pop song with flute accompaniment was up to no good. Prince had resisted the allure of hip-hop up until this song, but he gave up on this track, and the world is better for it.

Prince’s Christianity has always been directly at odds with his wanton sensuality. He became a less interesting artist when he succumbed to religion because the occasional song about Christ lost its weirdly libidinal contrast. “The Cross” is the spiritual center of “Sign ‘o’ the Times”; after a series of songs about sex and destitution, this meditation on faith-based sacrifice carries a tremendous charge. It’s also a great build song. It starts with a simple guitar riff and then blows out into something sacred and wonderful.

A perfect pop song. It’s Prince singing to his ex-girlfriend after a lousy breakup; she’s now with another guy, and yet, now that she’s gone, he’s never been more in love with her. Mitch Ryder had a minor hit with the song years later, but unlike several songs of his that were covered by other artists, Prince’s rendition is vastly superior. The lyrics get progressively darker, but Prince’s sense of humor about the whole sorry affair never vanishes. This is a song of bemused heartbreak.

Listening to one without the other is like splitting up Queen’s “We Will Rock You” and “We are the Champions." These songs are the victory lap of the film “Purple Rain." Prince (aka The Kid) has made amends with everyone in his life, and now he’s on top of the world. For whatever reason, one ebullient song wasn’t sufficient to put across the joy of the moment, and no one’s ever questioned Prince’s instincts on this.

“Life it ain’t real funky/Unless it’s got that pop.” “Around the World in a Day” is a socially conscious LP, and this is the song that best gets across Prince’s concern for the day-to-day struggle of the working class. It’s about despair, bad luck and, ultimately, drug addiction. Although Prince hadn’t hurt for money since maybe his youth, he was able to believably sympathize with the plight of poverty-stricken individuals. The funky bass line casually guides the song to its downbeat conclusion.

The first single from “Graffiti Bridge” was the final track recorded for the LP. It’s a bizarrely accusatory song; Prince is trying to rise above the treachery of a lover/friend, but he winds up lashing out at the conclusion. Genre-wise, it’s too halting to work as a dance track, and it’s certainly not a ballad. It’s the weird kind of in-between song that only Prince could write and record, and it stands out for these reasons. Most importantly, it’s got a killer melody.

A great, contemptuous ballad directed at a lover who didn’t know how great he had it. For a guy with a rather impressive dating track record, Prince had a tremendous capacity for dredging up romantic resentment. It’s not a terribly complicated song. The chorus states that “you need another lover like you need a hole in your head” (truncated in the title by Prince because that’s what Prince does). But the hook is irresistible, and the lyrics are endlessly inventive. 

One of the goofiest songs of Prince’s career has the musician asking his oppressor if they would take him more seriously as a dolphin. It’s not even a metaphor. Prince defiantly tells the subject of the song that they “can cut off all my fins,” but he’ll never bend to their will. And if they kill him, he’ll be resurrected as a dolphin. That’s the gist of it. What’s it doing on this list? It’s got a gorgeous melody and one of Prince’s most passionate guitar solos.

Prince’s vision of the apocalypse, and the preceding party, has never sounded more attractive. This is his finest homage to Sly & the Family Stone; each lyric is sung by a different member of the band in a different vocal register. The full LP version is a glorious work of art that’s been tarnished over the years by excessive radio play of the cut-down single edit.

Prince was never more in love than when he married Mayte Garcia, with whom he had a child who lived a whole week before succumbing to a rare congenital disease called Pfeiffer syndrome. Much of “Emancipation” reckons with the death of this baby, and it’s all unbearably sad. This song, however, finds Prince pouring his heart out to Mayte, pledging his loyalty and evincing an undying loyalty that was entirely new for him. They eventually divorced, but for several years Prince’s music took on a painfully sincere quality. He was never more human.

“Do you want him? Or do you want me? ‘Cuz I want you!” Some guys want to be John Cusack forlornly blasting Peter Gabriel’s “In Your Eyes” from a beat box outside of Ione Skye’s house. Men of honor want to take the stage and sing these words to a beautiful woman like Apollonia, who’s thrown them over for Morris Day. Prince mostly hangs out in his falsetto for this track, but he slides out of it when he needs to get real. Vocally, it might be the best thing he ever did.

Prince and funkmaster general George Clinton duet on one of the dirtiest songs of Prince’s career — and it’s worth noting that the song used to be much filthier in an earlier incarnation. (Hint: “funk” replaced a more indecorous f-word.) This song was largely ignored when “Graffiti Bridge” was released, and it’s high time people give it another listen and hear what they’re missing. The lyrics are juvenile at times (it imagines funkiness as a drug for which one can test positively), but Prince brings it home at the end with an impassioned plea for excessive copulation. They didn’t call him “His Royal Badness” for nothing!

From nastiness to absolute innocuousness. This is a whimsical ditty about a strange young woman named Cynthia Rose who kept these two odd items in the title in her lunchbox. Lyrically, it’s amusing and totally risible; as a pop song, it’s absolute genius. Prince jumps right on top of the melody with a piano intro and bangs out the song quickly. It’s wonderful, and yet it didn’t make the final cut of “Sign ‘o’ the Times.”

A party track with a conscience. One of the best songs on Prince’s “Dirty Mind” keeps the dance floor rocking while eschewing ignorant notions of sexuality and race. Uptown is a utopian place (based on a neighborhood in Prince’s native Minneapolis) where revelers can lose themselves in a non-prejudicial fervor. It’s an early mission statement from Prince, who often embraced androgyny before converting to Jehovah’s Witnesses. (Sly & the Family Stone veteran Larry Graham deserves a mighty amount of blame for ruining Prince.) It’s inclusive, sexy and fun — and, boy, does it get down.

A low-key pop song that gets by with a minimal amount of effort. Prince was so talented that he could throw away a song about nothing (and “Cream” is about nothing), and it would slowly reveal itself as an immaculately crafted single with elegant instrumentation. When Prince sings, “Look up in the air, it’s your guitar," he should be laughed off the planet. Instead, it’s the coolest thing anyone’s ever said, and the ensuing guitar solo is exquisitely unassuming. This is an immensely pleasurable song.

There is no bass line. It’s not there. It doesn’t exist. And no one ever questioned it until a more musically inclined individual pointed it out. This was one of Prince’s favorite tricks; he dropped the bass out of “Kiss,” and it might’ve been his biggest hit since “When Doves Cry.” But it wasn’t a gimmick. It was an instinctive understanding of what the song needed, and for reasons we’ll never understand, “When Doves Cry” didn’t need bass. You can’t argue with success.

Prince’s lust letter to a young fashion model named Cindy Crawford is significant because if the lyrics are any indication, he didn’t close the deal! This is a wild, shockingly desperate song that gets a bit weird when Prince seems to involve percussionist Sheila E. in a drink-spiking errand. Everyone was wild about Ms. Crawford in the late 1980s, but for a guy who was cycling between Apollonia, Martika and Kim Basinger, it’s hard to understand the desperation. And yet you listen to the song, and Prince explicitly makes the case.