Essential Prince: His greatest songs of all time, ranked

Designed as a throwback slow jam, “Breakfast Can Wait” delivers on that front … at least at first. The shimmering smooth soul is seductive but Prince gets restless: not only is the rhythm slightly unruly, he spends the back half of the song layering sped-up vocals, the Chipmunk harmonies being a clear indication that the Purple One doesn’t always take himself too seriously.

Anchored on a slinky, slippery glam groove, “Cream” flips T. Rex’s “Bang A Gong (Get It On)“ on its head. Where Marc Bolan wallowed in cheerful sleaze, Prince opts for seduction, singing “Cream” with a sly grin and draping his basic boogie in satin, so it has a smooth, alluring polish.

The culmination of a smooth soul infatuation that ran through his records of the early 1990s, “The Most Beautiful Girl In The World” feels like it was written for a 1970s vocal group like the Stylistics or the Delfonics to sing. Not quite a slow jam but certainly not funk, “The Most Beautiful Girl In The World” is an ebullient romantic soul tune, a song that’s pointedly not a seduction: it’s a joyous celebration of sustaining, nourishing love.

A pointed nod to the synth-funk that propelled him to fame in the early 1980s, “Black Sweat” also felt as nimble and new as the work of such Prince disciples as the Neptunes when it was released back in 2006. The rhythm is so infectious it might take a moment to realize how Prince spliced futuristic funk with a down-and-dirty vamp in the style of James Brown: the invention might not be placed in the foreground but it’s why “Black Sweat” is the freshest and freest of Prince’s latter-day singles.

Thrown away on his last album for Warner, “Dinner With Delores” finds Prince reviving the psychedelic-pop of his Around The World In A Day era. His approach is relatively streamlined this time, lacking the trippy excesses of his paisley-speckled funk, but its central guitar riff jangles like the Bangles and the song is propelled by one of his sweetest melodies.

Variety is the calling card of the double LP Sign O’ The Times, but even within that eclectic world “The Ballad of Dorothy Parker” stands out through its quiet quirkiness. Everything on the track sounds slightly muted, forcing the listener to concentrate to understand the arc of Prince’s flirtation with the waitress Dorothy Parker. That close listen also reveals such details as the dancing harmonies, percolating synth-bass, and a seamless allusion to Joni Mitchell, all of which intertwine in a singularly bewitching fashion.

A dense, danceable, and considerably chaotic jam, “Batdance” is a collage pieced together from elements of Prince’s soundtrack for Tim Burton’s 1989 theatrical adaptation of Batman along with parts of the film itself. Prince pulls hooks and sounds from fully finished tracks then stitches them together with dialogue samples and a drum machine seemingly set on speed dial. The result is gloriously strange, one of the weirdest singles to ever top the Billboard charts.

An ominous, almost haunted single, “Thieves In The Temple” is as lean and skeletal in its own way as either “When Doves Cry” or “Kiss.” Much of it finds Prince singing over a skittering rhythm, supported by synths that ring like church bells and claustrophobic harmonies, the tension broken by guitar squalls that feel like pleas. “Thieves In The Temple” is unusually unsettling for Prince, a song where a control freak feels his world slipping away.

Prince may be trading in various spiritual myths on “7” but don’t bother decoding the true meaning behind the song’s portentous lyrics: it’s enough to know that he’s suggesting some sense of mystic deliverance. That sense of transcendence is delivered by the song itself with its buoyant harmonies and towering guitar punctuated by a sitar that suggests psychedelic liberation as much as India.

The flip side of “Raspberry Beret,” “She’s Always In My Hair” portrays a faithful love as something of an annoyance: whenever Prince finds his hopes and dreams aimed in the wrong direction, she’s there in his hair, telling him how much she cares. Prince marries this skewed sentiment to a heavy psychedelic churn, one where the rhythms compete with sawing synthesized strings, a combination that’s strangely reassuring and hypnotic.

The song that inspired Tipper Gore to launch the Parents Music Resource Center, “Darling Nikki” seems comparatively tame in comparison to the truly outrageous songs from Dirty Mind; there’s no incest, no threesomes, no seducing a bride on their way to the altar. Nevertheless, Prince’s ode to Nikki—who he meets in a hotel lobby “masturbating to a magazine,” a line that scandalized Gore—feels filthy thanks to the Revolution turning the guitar-heavy vamp into a tight, cathartic rocker that climaxes with an orgasmic shout by Prince.

Opening the second side of Dirty Mind, “Uptown” feels ever so slightly a throwback to the Prince of the late 1970s: its funk is a little more straightforward than “Dirty Mind,” relying less on synth-pop and freaky fantasies. Listen closely, and “Uptown” reveals itself as a crucial part of Prince’s futuristic funk, a place where everybody unites on the dance floor: “White, Black, Puerto Rican/Everybody just a-freakin’.” Prince envisions “Uptown” as a utopia and that inclusivity is infectious.

Originally intended for Prince’s Camille project—an alter-ego where he sang in a sped-up voice meant to suggest a feminine singer—“Strange Relationship” wound up on Sign O’ The Times, where its walloping rhythms contrasted winningly with its insistent hooks. The beats are too heavy for the song to be pop, which in turn indicates how the song itself is deceptively sunny: underneath its bright surface, Prince offers insight into a codependent romance that’s turned destructive.

The first flowering of Prince’s taste for psychedelia, “Take Me With U” soars upon waves of strings and a bed of acoustic guitars, reaching full flight on a chorus where he and Apollonia pledge devotion. A number of the production tricks on “Take Me With U” suggest mid-period Beatles, but where the Fab Four were experimenting on Sgt. Pepper, Prince demonstrates careful craft here: there’s nothing out of place in either the lush arrangement or the sculpted melody, resulting in the purest pop tune on Purple Rain.

With its rich layers of harmonies, horns, and electronic rhythms, “Mountains’’ seems gloriously overstuffed, a place where Prince’s dance-pop and psychedelia intersect. At its core, it’s a hard funk number—Prince even mimics James Brown, shouting out “guitars and drums on the one”—but what gives “Mountains” its indelible character is all the extra elements, each competing for attention with Prince singing at the very top of his range.

A tense, skeletal piece of socially conscious funk, “Sign O’ The Times” feels utterly original in how it balances lyrical dread with musical deliverance, a signature Prince move since “1999.” “Sign O’ The Times” exudes the essence of Prince, so it comes as a surprise that he constructed much of the song out of presets on a Fairlight synthesizer: the identity comes not from the instrument but the arrangements, especially the stinging blues guitar that’s used as punctuation throughout the song.

Prince wrote the lurid “Sugar Walls” for the Scottish pop singer Sheena Easton back in 1984 and she returns the favor by being one of his two foils on “U Got the Look,” a sexually charged rocker originally intended for his Camille project. Easton trades barbs both with Prince and Camille, the cavalcade of voices giving the hard-charging number a sense of understated freakiness that its arena-rock chords don’t convey: the tension between the driving rhythms and florid arrangement is exhilarating.

A conscious revival of the sumptuous smooth soul emanating from Philadelphia in the early 1970s, “Money Don’t Matter 2 Night” glides by effortlessly—so effortlessly, it’s easy to overlook how Prince’s lyrics don’t quite match his mellow groove. “Money Don’t Matter 2 Night” finds Prince taking pointed jabs at greed and war, thereby giving the song a clear connection to another ’70s R&B trend, namely the socially conscious soul of Marvin Gaye, Stevie Wonder, and Curtis Mayfield.

Another Sign O’ The Times song where Prince demonstrates a deep knowledge of self, “I Could Never Take The Place Of Your Man” is a character sketch of a woman brokenhearted by a lover who “left her with a baby and another on the way.” Prince spots her on the dance floor and makes an overture before realizing he’s not qualified to be more than a one night stand, a confession delivered to a music that sounds joyful, even exuberant.

“Let’s Pretend We’re Married” is the one place on 1999 where Prince deliberately recalls the freaky funk of Dirty Mind, adding this blasphemous fantasy—he only wants to be married so they can “go all night”—to a list that includes “Head” and “Sister.” Musically, the computerized New Wave dance-rock “Let’s Pretend We’re Married” represents a step forward: it’s tightly controlled, never deviating from its robotic rhythms yet the song never feels static thanks to Prince’s strategically deployed vocal harmonies and synth stabs.

There couldn’t be a starker contrast from A-side to B-side than “How Come U Don’t Call Me Anymore.” A yearning blues, “How Come U Don’t Call Me Anymore” is stylistically a million miles away from the apocalyptic funk of “1999,” yet the song in its own way turned into a standard, garnering covers from Alicia Keys, Stephanie Mills, and Joshua Redman. The starkness of Prince’s original—it’s just him at a piano, wailing his heart out—makes it an ideal canvass for singers looking to turn this gospel-inflected blues into something of their own.

Prince sings “I’m not a woman, I’m not a man/I’m something that you’ll never understand” at the opening of “I Would Die 4 U,” echoing some of the pansexuality he essayed on “Controversy.” Where he designed that New Wave funk anthem to be deliberately provocative, there’s a sense of romanticism fueling “I Would Die 4 U,” conveyed not only in its titular plea but the soaring sigh of its melody, delivered by Prince in conjunction with Wendy & Lisa.

“Delirious” is lively and loose, a buoyant rocker that swaggers like Elvis Presley but bounces to New Wave synths. By wrapping his bygone boogie and a sterling synth sheen, Prince casually displays his deep understanding of the idiom of pop music: the structure is so simple, it’d sound good played in any arrangement, but he’s savvy enough to realize how to make this swinging little rocker sound fresh.

“Controversy” finds Prince refining the freakiness of Dirty Mind, hardening the synth-funk while pushing his ambiguity toward the forefront. He opens the song asking “Am I Black or white?/Am I straight or gay,” then proceeds to spend the rest of the song embracing both identities, reaching a climatic note with the chant “I wish there was no black and white, I wish there were no rules.” “Controversy” shows that Prince is following his own advice: he’s operating without a playbook, constructing a song that’s as rock as it is funk.

Chaka Khan turned “I Feel For You” into a massive hit in 1984, the same year that Prince ruled the charts with Purple Rain. At that point, the song was five years old, getting its initial airing on Prince’s eponymous second album. The original version doesn’t push the beats as hard as on Khan’s cover and that smoother touch has its own appeal, particularly since Prince’s falsetto helps the songs seem sweeter, even seductive.

Dirty Mind found Prince letting his freak flag fly, embracing all the perversity his early albums only hinted at. The album’s title track provides the musical and lyrical fanfare for the record, laying plain his carnal desires while also delivering a funk that feels futurist. Some credit must go to Dr. Fink, who wrote the synth riff that powers “Dirty Mind” but it’s Prince that decided to push that sound to its limit, creating a kinetic, kinky New Wave funk.

Appearing as the B-side to “When Doves Cry,” “17 Days” acts as something of a bridge between Purple Rain and Around The World In A Day. At its core, “17 Days” percolates to a synth-funk rhythm, an insistent beat to which Prince overdubs an elastic bass, chiming synths, and Wendy & Lisa harmonies, all suggesting a rich interior world that points toward the psychedelic-pop he’d make in just a year.

Another song slated for the Camille album that wound up on Sign O’ the Times, “If I Was Your Girlfriend” bends genres and gender. Delivered in a sped-up voice intended to convey a feminine side, Prince wonders how a relationship would be if his paramour was a friend, not lover. The existential issue of identity is heightened by the Camille voice, which is oddly empathetic and tender here; maybe Prince could only be this revealing if he hid himself under a mask.

Prince’s first number one R&B hit, “I Wanna Be Your Lover” places equal emphasis on funk and pop, its bright beat matched by its sunny hook. Relying on his falsetto, Prince sounds exuberant throughout “I Wanna Be Your Lover,” his good cheer helping to disguise his knowing delivery of the lyric “I wanna be the only one that makes you come … running.” Hiding a dirty joke within an infectious pop-R&B number is a signature move of Prince, one that finds its roots here.

“Another Lonely Christmas” belongs to a series of brokenhearted B-sides Prince released in the mid-1980s, this flip to “I Would Die 4 U” distinguishes itself through its blend of pathos and perversity. Prince mourns a lover who died years ago on the 25th day of December by remembering stories that paint a portrait of their romance. By the end of the song, he confesses he spends every Christmas night drinking “banana daiquiris ‘til I’m blind,” an absurd detail that’s central to this melodrama’s peculiar appeal.

The flip side of “Let’s Go Crazy,” “Erotic City” hits the sweet spot between freaky and sexy; its perversity is enticing, not alienating. Much of that allure is due to how the song is presented as a give-and-take between Prince and Sheila E. Sure, Prince overloads the song with electronically altered variations of his voice, each sounding freakier than the next, but by having Sheila E. share the chorus, he emphasizes that “Erotic City” is at its heart a dance between two lovers, not a solo seduction.

Closing the tour de force Sign O’ The Times, “Adore” is the sweetest, sexiest soul number Prince ever cut, a slow jam that recalls the smooth soul of the 1970s while feeling fresh and contemporary. Never released as a single, it earned its audience through the years, becoming an integral part of his songbook.

At the height of his Purple reign, Prince threw it all away to take an expressway to the Paisley Underground, the psychedelic revival emanating from the deepest recesses of Los Angeles. Around The World In A Day reached its pinnacle with “Raspberry Beret,” a trippy confection that sidelines funk for paisley pop hooks. As catchy as it is, “Raspberry Beret ‘’ is buoyed by Prince’s perverse sense of humor: line for line, this is the funniest single he ever released.

The hardest rocker Prince ever cut, “Let’s Go Crazy” finds the Purple One preaching that we “Better live now before the grim reaper comes knocking on your door.” The notion that it’s better to party because the end is around the corner is a close cousin to “1999" but where that synth-funk hit ran icy and cool, “Let’s Go Crazy” is red hot: it’s the sound of the id exploding, culminating in a volcanic burst of guitar.

“1999" is where Prince turns his synth-funk into a New Wave freakout, wallowing in a frightful apocalyptic imagery that’s equal parts nuclear holocaust and premillennial tension. All Prince’s fears take the shape of a bacchanalian party, one that feels especially wild due to his decision to split lead vocals with members of the Revolution, including Lisa Coleman. All the different voices undercut the ominous warnings of a computerized voice—one that deliberately echoes 2001’s HAL in the song’s opening moments—and help “1999" feel like a celebration

A dynamic piece of power pop whose exuberance camouflages its despair, “When You Were Mine” finds Prince pining after a lover who was perhaps a bit too audacious for his tastes. As he wanders through his back pages, he’s equally aroused and distraught by her infidelity and kinks; the pivotal line concerns how Prince never made a fuss when another guy was “sleepin’ in between the two of us.” His vocals convey heartbreak while the melody and hooks suggest joy, a combination that gives this punchy pop song real depth.

“Little Red Corvette” emerges from a fog of dry ice, its gilded synths giving the spiky funk-pop a tense and alluring nocturnal atmosphere. The creeping sense of seduction sets the stage for Prince’s highly charged tale of a one night stand, filled with automotive puns and knowing nods to horses and jockeys. There’s no suggestion that connection at the core of “Little Red Corvette” is anything other than carnal but Prince’s erotic pursuit isn’t single minded: It’s funny, sleazy and irresistible, a fling that you want to revisit over and over.

“When Doves Cry” turned Prince into a superstar in 1984, which is odd because the song is curiously off-kilter: its bass-less funk is ominous and mournful, while also sounding otherworldly and sensual. Prince sketches erotically charged scenarios that never succumb to overtly sexual imagery. The power is all in the tension, one that’s ratcheted up by black and white rhythms and fueled by Prince trying to navigate the role past trauma plays in his romantic relationships. “When Doves Cry” suggests more than it reveals which is why it retains its power and mystery decades after its initial release.

“Kiss” is Prince’s funkiest hit, an incessant vamp that’s deceptively lithe and lean. Singing at the highest reaches of his falsetto, Prince delivers bon mots tinged with his signature perversity, trading barbs, and soothing harmonies with Wendy & Lisa. Where most funk gets down and dirty, this is light and colorful, the momentum created through the deft deployment of vibraphones and guitars.

The cathartic climax to Prince’s feature film debut became his signature anthem—the song everybody plays as a tribute to the Purple One. Such an outpouring of emotion suits Prince’s most nakedly emotional song, a ballad filled with longing, empathy, and connection that reaches a full transcendence with its soaring closing guitar solo which summons all the feelings he couldn’t quite put into words.