Purple Perfection: Prince’s 40 Greatest Songs.


This Sunday, almost a year after his shocking passing, Prince’s full Warner Brothers music catalog – everything up to 1994 and two from 2014 – will finally hit streaming services such as Spotify and Apple Music. This includes his most seminal albums – 1999Purple Rain, Sign O the Times. With such a wide ranging catalog (more than half of Prince’s nearly 40 albums were recorded for Warner Brothers), now is as good a time as any to sit down and sift through the cream of the crop and come up with the 40 most essential Prince songs throughout his career, from chart topping smashes to long out of print obscurity.

40. Alphabet Street (Lovesexy, 1988)
Lovesexy was a largely adult affair, drifting towards the spiritual as opposed to the physical, but “Alphabet Street” provided a nice respite. It’s not life changing, and certainly pales in scope and overall artistry to some of his other singles, but it’s also incredibly catchy, recalling “Raspberry Beret” with its automobile references and psychedelic vibe. Make sure you get the album version with Kat Glover’s rap, as the song feels even slighter without it.

39.I Feel For You (Prince, 1979)
Chaka Khan did it better, but “I Feel For You” still holds a nice place as one of Prince’s best early numbers, and his own take certainly stands up well against Chaka’s 1984 smash. Prince’s take is more relaxed, with a breezy groove and vocal performance, and lays a nice framework for which Chaka (and Stevie Wonder) improved upon exponentially.

38. She’s Always in My Hair (The Hits / B-Sides, 1993 – originally recorded in 1983)
This mid-tempo love song backed “Raspberry Beret,” and later became a live staple. Prince obviously loved the song, as he always smoked it in concert, turning in passionate vocals and searing guitar work whenever it popped up in the set.

37. In This Bed I Scream (Emancipation, 1996)
Prince’s three disc kiss-off to Warner Brothers was a hit or miss affair, but it yielded some gems, most prominently this riveting tale of regret. Though it has a relatively gleeful hook and arrangement, the song’s lyric are pure heartbreak, buoyed by a series of vocal crescendos that stand out as one of Prince’s best studio performances. The song as a whole is one of his most underrated and exciting.

36. How Come U Don’t Call Me Anymore (The Hits / B-Sides, 1993 – originally recorded in 1982)
This smoky blues shuffle is probably Prince’s most beloved B-side and was also a live highlight for many years, with Prince pulling out some of his most daring and honest vocals: when he holds that long note on “Stiiiiilllll like it better….” you feel it in your soul.

35. Solo (Come, 1993)
This chilling Billie Holiday esque tale of isolation and loneliness might be Prince’s darkest: the lyrics, when read on their own, could be a suicide note. Its spooky quality is enhanced by Prince’s falsetto, by far the most ghostly it ever sounded. Despite its sparseness, it’s also one of his most evocative arrangements: if isolation had a sound, it would be the electric piano and harpsichord that serve as sole accompaniment.

34. Black Sweat (3121, 2006) *
This minimalist funk jam was Prince’s funkiest track in a long time. Accompanied by a playful black and white music video featuring the Artist and dancer Celestina Aladekoba, “Black Sweat” could’ve easily come from Prince’s early albums, between its seductive lyrics, tight groove and synth hook. Prince was back, and this time for good.

33. Musicology (Musicology, 2004) *
The title song from Prince’s 2004 comeback album is a nostalgic tribute to the music that inspired Prince, namedropping Earth, Wind and Fire, Sly & the Family Stone, Chuck D, and numerous others, as well as sampling some of his own biggest hits during the fadeout. After spending much of the early 2000’s looking to reestablish his presence after the somewhat bizarre symbol period, Prince discovered that the only way to do so was to return what he did best, bringing back the funk and soul that defined his early work. Musicology as a whole was a very welcome return to form, the first time Prince had felt fully like Prince since perhaps Diamonds and Pearls.

32. Adore (Sign O the Times, 1987)
This tender, angelic ballad comes as a welcome sense of relief after the largely dark affair that is the Sign O the Times record. Prince’s falsetto reaches new and exciting heights as he croons of love everlasting, as this time he ain’t ‘fucking just for kicks.’ Just don’t smash up his ride.

31. Pop Life (Around the World in a Day, 1985)
One of Prince’s many ‘take a look around, the world may be shit but you gotta live anway’ anthems, “Pop Life” coasts along on a breezy groove as Prince poses a series of questions to its forlorn listener: “Is the poverty bring you down?” “Is the mailman jerking you ‘round” “What you puttin’ in your nose?” It’s an effective critique on 1980s-era excess, even if it isn’t as dynamic as a “Let’s Go Crazy” or a “1999.”

30. When You Were Mine (Controversy, 1981)
A soulful retro ballad with a killer hook, “When You Were Mine” quickly became one of Prince’s most covered songs, with the likes of Mitch Ryder and Cyndi Lauper – among others – each quickly trying their hand at it. It’s not hard to see why: “When You Were Mine” is a perfect pop song, with an instantly memorable melody and a simple but relatable sentiment that struck a chord. It wasn’t a big hit at the time of its release, but it’s since become a deserved classic.

29. Days of Wild (Crystal Ball, 1998)
Prince had a love-hate relationship with rap, acknowledging its musical significance while often expressing dismay at its perceived vulgarity and embrace of violence and misogyny. “Days of Wild” allowed Prince to successfully experiment with the genre while taking shots at the elements he disapproved of such as the glorification of drugs (“Pop, guns and weed? Brother please! We’re much too wise for this nonsense…”), misogyny (“A woman everyday should be thanked, not disrespected, not raped or spanked”), and fashion (“Tennis shoes and caps, now that’s phat”). It’s one of his most aggressive and original songs, as well as one his most effective uses of profanity for emphasis, something that the song lost after Prince’s religious conversion.

28. U Got the Look (Sign O the Times, 1987)
“Here we are folks, the dream we all dream of…boy vs girl…in the world series of love…”

And with that, Prince and Sheena Easton takes on a four-minute thrill ride with this grand-slam of a pop rocker. If Bogie and Bacall were a 1980s’ pop duo, this is the kind of sexy, classy number they’d specialize in. Prince and Easton’s feisty vocal volley has often been imitated, but never duplicated.

27. Diamonds and Pearls (Diamonds and Pearls, 1991)
The title song from his 1991 album, this sparkling ballad may seem somewhat saccharine on paper, but its glowing arrangement, warm vocal and the presence of the dynamic Rosie Gaines elevate it to something much greater. Even if some of the lyrics rely too much on the ‘moon / June’ rhyme scheme as opposed to more dynamic and evocative wordplay, they still are representative of the significant growth and sophistication Prince had gradually been demonstrating in terms of portraying relationships, a trait he began experimenting with as early as “Kiss.”

26. 17 Days (The Hits / B-Sides, 1993 – originally recorded in 1983)
To show just how much of a roll Prince was on in terms of quality from 1982-85, this haunting up-tempo ballad was only considered good enough to a B-side. The song it backed? “When Doves Cry.” Prince gives one of his most effective vocals, while The Revolution turn in one of their strongest performances in the studio, particularly Wendy & Lisa, whose spectral backing vocals are evidence of just how essential a component they were to Prince’s signature sound.

25. Dreamer (Lotusflower, 2009)
Arguably the best song Prince wrote during his mid-2000’s artistic and commercial resurgence, “Dreamer” is a searing, angry number that touched on racism, politics, and Prince’s infamous belief in chemtrails. With a chunky groove and biting, often clever lyrics (“Peanut butter logic, served on a bed of lies…”), this is the kind of song Prince should’ve focused on in what turned out to be his final years. It’s certainly more interesting than “Guitar.”

24. Delirious (1999, 1982)
This wily gem gets overshadowed by the other two breakout hits from 1999 (the title song and “Little Red Corvette”), and while it may not be as ambitious as either of those two tracks, it’s still an absolute blast: one of Prince’s catchiest pop confections, its cheery, zig-zaggy keyboard riff stopping at nothing to worm its way into your head as Prince delivers one of his most playful, seductive vocals.

23. Something in the Water (Does Not Compute) (1999, 1982)
While Prince would portray the themes of paranoia, insecurity, and general emotional vulnerability more effectively in later songs (“Thieves in the Temple,” “The Beautiful Ones”), “Something in the Water” still remains one of Prince’s most underrated and effective tracks. It’s also one of his weirdest, boasting a spin-cycle rhythm, hidden, almost subliminal vocals (the way Prince simply whispers the word ‘bitch’ at one point is downright sinister), and maybe the most chilling moment in Prince’s entire recording history, as he unleashes a series of screams that sound like they come from the deepest, darkest pits of hell. Don’t listen with the lights off.

22. Do Me, Baby (Controversy, 1981)
Probably the song I would like to most go back in time to watch Prince record in person: just what the hell was it like to watch him unleash those torrential, orgasmic screams in person? The pinnacle of his early bedroom soundtracks, Prince isn’t fucking around on “Do Me Baby”: it’s an intense, over-the-top, erotic romp that, like the best sex, takes it time to build up to an incredible climax, ebbing and flowing at key times, going in unpredictable and exciting directions when you least expect it. When Prince utters, “I won’t stop until the war is over,” you can’t help but submit. Christian Grey ain’t got nothing on the Purple One.

21. I Could Never Take the Place of Your Man (Sign O the Times, 1987)
A forlorn soul ballad disguised as a retro throwback to the boardwalk sound of the early 1960s’, this little gem is proof that stripped of the sexual innuendoes, ear piercing screams and other histrionic signatures, Prince was just a damn good pop songwriter: this is the kind of song Carole King could’ve knocked out for The Drifters and made into an instant classic, but as such it remains a relatively obscure entry in his catalog (though it did make the Top 10). I’ll touch more on Prince’s maturation of a songwriter in regards to his portrayal of women and relationships as this article progresses, but the depth and sensitivity he portrays in this song marked a major progression, as it is unlikely he could’ve come up with something this elegant and adult in both subject matter and musicality around the time of “Jack U Off.”

20. Darling Nikki (Purple Rain, 1984)
Also known as Tipper Gore’s all time favorite, this graphic tale of a one-night stand is one of Prince’s darkest and most unique songs: its metallic, slinky, almost robotic guitar riff, the longing vocal and the NSFW lyrics made for a challenging but nonetheless compelling listen. Moreover, it stands out for being one of the few tracks in Prince’s catalog where intercourse isn’t a positive, transformative experience: the narrator is clearly haunted by Nikki’s abandonment, punctuated by one of Prince’s most psychotic screams begging her to come back.

19. I Wanna Be Your Lover (Prince, 1978)
In just under three minutes, Prince’s first major hit single managed to establish the image that would define his early career: a fearless, androgynous paramour of love and lust unafraid to shatter boundaries. Who else could pull of a line like “I wanna be your brother, I wanna be your mother and your sister too” so confidently?

18. Let’s Go Crazy (Purple Rain, 1984)
Prince’s pre-eminent showstopper, a ‘live in the moment’ anthem with the most memorable opening sermon in pop music, “Let’s Go Crazy” is a musical funhouse that delights, frightens and excites. Its lyrics urge the joy of life while also confronting the specter of death (much has been made of the haunting coincidence of Prince having died in an elevator, a metaphor for hell that is echoed in the song’s pre-chorus refrain). Few have approached mortality with such abandonment and enthusiasm.

17. Cream (Diamonds and Pearls, 1991)
His last chart-topper, “Cream” is also the last of Prince’s erotic anthems to gain traction with the general public, as he moved towards a more spiritual direction as the 1990s’ went onward. Mixing Delta blues with a New Jack groove, “Cream” was a breath of fresh air after Graffiti Bridge left his career in somewhat of a limbo state, ensuring fans that there was still a lot of ground for Prince to cover and that his muse was still very much with him. Also, has a cowbell ever sounded sexier?

16. The Most Beautiful Girl in the World (The Gold Experience, 1995)
This could be considered Prince’s last true ‘classic.’ That is not to say he didn’t have anymore great songs or albums, or that he didn’t write songs that should be regarded as classics (“Dreamer”), but this incredibly touching ballad was the last song in Prince’s lifetime to have anywhere near the impact of his previous classics. More than just a great pop single, “The Most Beautiful Girl in the World” is one of his most affectionate ballads, as well one of his most evocative studio arrangements, tastefully making use of natural sound effects such as water rippling and animals. The song also features Prince’s greatest vocal take, spanning every facet of his range, most notably his rich, low natural baritone.

15. Controversy (Controversy, 1981)
“People call me rude. I wish we all were nude. I wish there was no black or white, I wish there were no rules.”

When Prince hit the scene, he was unlike anything that had been seen; a hybrid of James Brown, David Bowie and Smokey Robinson, he was a dichotomy: his songs portrayed the sort of sexual machismo of big voiced Barry White types, yet his feminine falsetto and androgynous stage presence made for a compelling parallel. Questions about Prince’s personal life came into question, and “Controversy” – the song and as well as the album – was a no-holds barred “Fuck You” set to the nastiest of grooves.

14. 7 (Love Symbol, 1992)
The flip-side to “Thieves in the Temple,” possessing a similar Middle Eastern sound but being much more optimistic and upbeat in nature. Essentially the theme song to his film 3 Chains O Gold, “7” is yet another of Prince’s ‘love will conquer all’ anthems, and it’s one of the best: between the aforementioned Mediterranean inspired arrangement and some of his most evocative lyrical passages, “7” is simply sublime, an irresistible paean to hope.

13. I Would Die 4 U (Purple Rain, 1984)
The penultimate song in Purple Rain, “I Would Die 4 U” isn’t a song so much as a pledge: I’m going to give you my all…just don’t expect to understand all of it.’ It was a promise to always keep us guessing, to keep us intrigued and challenged. That promise was one kept throughout his entire career, as he constantly sacrificed one phase for the next to keep fans wanting more, whether they understood what he was doing or not.

12. Thieves in the Temple (Graffiti Bridge, 1990)
There isn’t much good you can say about Graffiti Bridge, Prince’s directorial debut and his ill-fated sequel to Purple Rain. The soundtrack, for the most part, is quite clunky, with lots of forgettable contributions from supporting artists, as well as some tepid tracks from the Artist himself. Still, “Thieves in the Temple,” with its Middle Eastern sound and dark lyrics of paranoia and mistrust, rose above the pack and immediately established itself as one of Prince’s most original works of his career. It also became one of his most revered, eventually becoming a jazz standard after Herbie Hancock famously covered the song in 1996, once again how wide Prince’s influence spanned.

11. Sometimes It Snows in April (Parade, 1986)
This quiet piano ballad is the subtle cousin to “Purple Rain’s” bombast: a gentle, elegiac tribute to a spirit gone too soon. In the wake of Prince’s passing, the song gained a notoriety it never quite gained during its lifetime (given its retroactively ominous title, how could it not?) Ignoring its haunting parallels with Prince’s actual passing, the song still functions flawlessly as a meditation on the intertwining of pain and pleasure, on how death and rebirth go hand and hand, and how all good things must come to an end.

10. The Beautiful Ones (Purple Rain, 1984)
The first emotional high point of the motion picture, this is a Prince ballad like no other: he never so convincingly portrayed such vulnerability or emotional nakedness before or since, at least when it comes to romance. Starting off as a tender, falsetto driven plea, it builds up to an absolutely devastating conclusion, with Prince screaming at the edge of his voice for his lover to make the choice, “Do you want him? Or do you want me?” Apollonia may have taken her time, but the rest of us never gave it a second thought.

9. Raspberry Beret (Around the World in a Day, 1985)
A love song about a colorful, obscure sartorial article, a girl who ‘wasn’t too bright…but knew how to get her kicks,’ and a motorcycle ride to Old Man John’s farm? This psychedelic throwback was the kind of quirk gem only Prince could come up with, and turn into a massive hit at that. One of his most endearing compositions, the whimsy of “Raspberry Beret” offered the perfect counter to the grandiose drama of “Purple Rain,” and further established Prince as a versatile and unpredictable force in pop music.

8. Sign O the Times (Sign O The Times, 1987)
The flip side to “1999.” Whereas the earlier track urged us to set aside the woes of the world, this one confronts them head-on: AIDS, crack, the Challenger explosion and nuclear fallout all get name dropped in some form or another throughout this track, as Prince’s sullen vocal muses of a world gone dark and getting darker. Unlike “1999,” release won’t come from earthly pleasures, but from the stability of love and family. Prince’s forays into socio-political writing were hit or miss, but this was a home run (the goofy ‘…we’ll call him Nate’ line notwithstanding).

7. 1999 (1999, 1982)
I wish I could’ve been there when those synths cut through the airwaves in 1982. Prince’s seminal breakthrough party anthem perfectly undercut the swath of fear that was quickly sweeping through Reagan’s America. “1999” put everything into perspective: “Everybody’s got a bomb, we could all die any day, but before I let that happen, I’ll dance my life away.” As the decade grew more turbulent, Prince’s attitude became essential in the face of AIDS and Star Wars. It’s just as relevant as ever in the face of Trump. Truly a timeless song no matter what year.

6. Kiss (Parade, 1986)
That ‘waka-waka’ guitar riff. That air-tight groove (maybe The Revolution’s best studio take). That agile falsetto. The endlessly quotable one-liners (“Act your age, mama, not your shoe size…”). “Kiss” is the perfect pop single, and captures Prince in the best of both his worlds. Equal parts bawdy and sophisticated, this song did more to cement his public image than perhaps any other single post-Purple Rain, as a pop star, as a sex symbol, and as a songwriter. Like “Little Red Corvette,” it also represented a massive step forward in Prince’s portrayal of sexuality and relationships: he is not concerned with looks, flirty pickup lines, or zodiac signs, just unfettered commitment (and your kiss).

5. If I Was Your Girlfriend (Sign O the Times, 1987)
From what warped corner of Prince’s mind did he pull this from? Do we even want to go there? Who knows? The 1980s’ gave major momentum to the stalker ballad (“Every Breath You Take,” “Somebody’s Watching Me”), but leave it to Prince to turn the genre on its head and come up with something unlike anything he, or possibly anyone, could’ve conjured.

Inspired by his breakup with Susanna Melvoin, “If I Was Your Girlfriend” speaks of a longing to relate to your lover on the most intimate level, in this case their best friend. That Prince uses gender specific terms is key to understanding the narrator’s frustration, as he feels that his machismo makes him incapable of understanding his lover’s deepest emotions, so much that Prince deliberately sped up his voice to sound more feminine. Both creepy and beautiful, “If I Was Your Girlfriend” is an endlessly fascinating song, one that few have dare attempted to recreate because no one could do it like Prince could.

4. When Doves Cry (Purple Rain, 1984)
Dig, if you will, the genius of Prince’s biggest selling and arguably most beloved single: he played every single instrument. He did all the vocals. He defied conventional wisdom by not even giving the song a bass line, because he wanted it to truly sound different than anything else on the radio at that point. To say he succeeded is an understatement: in the midst of Reagan-era materialism, slick Casio riffs, and Yuppie excess, Prince broke through with an intensely personal tale of a man unable to come to terms with his father’s emotional distance, leaving him spiritually frigid and unable to relate to the one woman who could help him. If 1999 was the catalyst for Prince’s maturation as an artist, “When Doves Cry” was the culmination, his most mature and elegant composition to date, and one of those songs that significantly altered pop music going forward. 33 years later, it still feels fresh.

3. Little Red Corvette (1999, 1982)
There are a variety of factors that allow “Little Red Corvette” to stand head and shoulders above all of his other tales of sexual ribaldry. While there’s certainly much to enjoy in early numbers such as “Soft and Wet” and “Head,” they are rather immature and pedestrian, with little concern for subtlety or tastefulness. With 1999 as a whole being Prince’s true artistic breakthrough, it only made sense that his signature erotic side would too display a major leap in quality.

A marked departure from those earlier numbers, “Little Red Corvette” is a three-act play set to music, beautifully detailing the sexual awakening of its protagonist. The tapestry of tension weaved by the now-famous synth intro was the first clue that this would no ordinary tryst, but something much more sensuous, mysterious and ultimately satisfying. Those first lines confirm our suspicions:

“Guess I should’ve known by the way you parked your car sideways, that it wouldn’t last.”

This isn’t the confident paramour of “Head” or “Dirty Mind.” This is Prince as a novice, clearly experiencing his first adult moment of stimulation, with a woman who intimidates him as much as she excites him. Just the mere fact that she bought condoms along (“…pocketful of horses, Trojan and some of them used…”) is enough to rattle his confidence. And yet, he comes to the same conclusion: “it was Saturday night, I guess that’s makes it alright…”

The song’s climax (no pun intended) is maybe Prince’s best recorded moment, a heady rush of orgasmic release that only Prince could conjure through sound. Even as the song fades out, you know Prince and the band don’t want it to end. It feels too damn good.

2. Nothing Compares 2 U (The Hits / B-Sides, 1993)
It’s the song every songwriter wishes they could write: the evergreen. A song so deceptively simple, yet so universal in its appeal, that it could’ve been written at any time and become a classic, regardless of whatever current musical tastes. Everyone from Sinead O’Connor to Chris Cornell has tried their hand at the song, undoubtedly the most famous Prince has written for another artist. While the lone version Prince released himself – a duet with Rosie Gaines on his 1993 greatest hits anthology – is somewhat tepid and lacking, there are numerous live performances throughout the year that clearly show how proud he was having written this song.

1. Purple Rain (Purple Rain, 1984)
No matter how obvious a choice it was, there’s no way “Purple Rain” could not top this list. Forget that it may be ‘overplayed.’ Forget that it was the one everyone jumped to do a pedestrian cover of after his passing. From a musical, lyrical, artistic and emotional standpoint, “Purple Rain” is Prince Rogers Nelson’s masterpiece. It’s all at once tragic and triumphant, downtrodden and uplifting, sorrowful and hopeful. The song is a microcosm of everything that makes Prince great: passionate howls, tender falsetto cooing, sensitive, sensuous lyrics and one of the most legendary guitar solos in rock music, a ferocious torrent of sound that sweeps you up and keeps you enraptured. When the solo dies down into Prince’s final dove-like falsetto cooing, it’s like the storm has passed and the most beautiful rainbow has emerged.

After his passing, “Purple Rain” felt like an edict: “Honey, I know times are changing. It’s time we all reach out for the new. That means you too.” Prince is gone. The times have indeed changed. We need to move forward, embrace the new, those who Prince blazed a path for and continues to inspire. Things may not stay the same, but neither did Prince.

* recorded during his time with Universal, will not be available for streaming.

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