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Prince, in 14 songs that show why he's a musical legend

Dylan Matthews is a senior correspondent and head writer for Vox's Future Perfect section and has worked at Vox since 2014. He is particularly interested in global health and pandemic prevention, anti-poverty efforts, economic policy and theory, and conflicts about the right way to do philanthropy.

Prince, who died Thursday at age 57, was a singular force in 1980s music. He drew from the decade's biggest trends — synth-pop, modern R&B, New Wave — but melded them together with such ease as to make the end product feel timeless.

He had the pop intuitions of Michael Jackson, the guitar heroics of Van Halen, and the mythology and pageantry of David Bowie. His work was immediately accessible but insistently transgressive, and he remained defiantly in control over it and his own image even as other artists were crafted by their labels.

Covering his career could fill several books, but here are 14 essential songs that help explain why he was such an iconic figure. Unfortunately, due to Prince's aggressive views on copyright many of these tracks aren't available for streaming; we've included what we can, and the rest are available on iTunes and other sites.

1) "I Wanna Be Your Lover"

Prince's first major hit — released in 1979 — was a fairly straightforward disco track, sung in a Barry Gibb falsetto with a guitar part that wouldn't feel out of place on a Chic song. It lacks the instrumental virtuosity and stylistic experimentation that would define Prince's later work. But there are nonetheless signs of the artists he'd become, not least in the song's bracing sexual frankness. Prince doesn't want to be the only man you love — he wants to be the "only one you come for."

2) "Sister"

Prince was under pressure to follow up the surprise success of "I Wanna Be Your Lover" with an album full of similarly sunny, bright pop tunes. Instead, he released Dirty Mind, one of the best albums of his career but also one whose lewdness and shock value remain startling 36 years later. There's "Head," the subject matter of which should be obvious ("But I just a virgin, and I'm on my way to be wed / but you're such a hunk, so full of spunk, I'll give you head"); there's "Uptown," an account of an orgy; but most scandalous of all is "Sister," a purposefully over-the-top celebration of the joys of sex between siblings ("My sister never made love to anyone else but me … Incest is everything it's said to be").

Unsurprisingly, the album threatened his career in a number of ways. His biographer Ronin Ro notes that Warner Bros. included a sticker on copies of the albums sent to DJs telling them to "audition prior to airing"; "they ended up not being able to play some lyrics," Ro writes. Some record-store owners were deterred by the cover, which depicted Prince in briefs, a blazer, and not much else.

But critics, at least, were on board. Rolling Stone's Ken Tucker raved, "Dirty Mind is a pop record of Rabelaisian achievement: entirely, ditheringly obsessed with the body, yet full of sentiments that please and provoke the mind."

3) "When You Were Mine"

Amidst all the smut, Dirty Mind also included a song that would become a bona fide pop standard, covered by everyone from Cyndi Lauper (see above) to Ani DiFranco to Tegan & Sara. "When You Were Mine" is an earnest, brutal account of a love triangle with Prince the odd point out, unable to get over the loss.

Of course, this being Prince, things aren't that simple below the surface. As AllMusic's Stewart Mason notes, "barely-hidden in the lovelorn lyrics is the reason why Prince is so upset that his girl left him: he'd invited this guy over for a threesome and it turned out that she liked him better."

But the song endures outside the context of Dirty Mind because of its universality. It can be a regretful reflection on a threesome; it can serve as a sly acknowledgement of a past partner's bisexuality (as in Lauper's version, which doesn't change gender pronouns and acknowledges her cross-dressing boyfriend left her for a man); or it can just be a beautiful, brutal breakup track.

4) "Ronnie, Talk to Russia"

Prince was never not political; his very status as an unapologetically sexually aggressive black man willing to bend gender norms and uninterested in conventional norms of masculinity made him a political figure of no small importance. But he was also explicitly interested in capital-P politics almost from the beginning, as you can see on this song from his 1981 album Controversy.

The lyrics are fairly simple — "Ronnie talk to Russia before it's too late / Before they blow up the world" — and at points hackneyed (he sings about going to the zoo to see "left-wing guerrillas"; get it? do you get it?). But his concern over the arms race presages the apocalyptic tone of much of his later work, starting with the Millennarian anxieties of 1999.

5) "1999"

Prince was not exactly an obscure figure before the album 1999, but it was nonetheless crucial in shaping his public image into the one that persists today. And at the core of that process was the title track, "a single that spoke of the funkiest Armageddon scene you've ever heard of," in the words of Touré, author of I Would Die 4 U: Why Prince Became an Icon. "It was a perfect gen X dance song built on the idea that the world's about to end so, to hell with it, let's dance."

The video contains many of the distinctive visual elements of Prince-ism: the purple motif, the jacket, the uniformed band. The Revolution — his famed backing band — gets key billing, with Lisa Coleman and Jill Jones flirting a bit to sneak some sexuality-bending into the proceedings.

In part, the futurist themes of the song reflect the means of its creation: tired of his intermittently available drummer, he came to rely increasingly on his Roger Linn drum machine, one of the first ever made. "With technology providing instant results," Ro writes, "1999 morphed into becoming all about Prince running computers."

6) "Little Red Corvette"

A sharp contrast to the global, apocalyptic scale of "1999," "Little Red Corvette" was the kind of song Prince had mastered at this point: what Touré calls a "masterfully written pornish sex story song." It chronicles Prince's encounter with a woman more experienced than him, intimidatingly so. "In this song," Touré explains, "it's as though Prince is a sexual athlete whose competition is women who are more sexual."

This was one nice aspect of Prince's sex tales: While by no means perfect, they often ascribe a great deal of sexual agency to his female partners, making them more powerful or experienced than him. The tone isn't dismissive, but almost worshipful. Prince stands out from most of his male contemporaries for embracing women's sexuality in a genuine, not brutish, manner.

7) "When Doves Cry"

It almost feels superfluous to explain why "When Doves Cry" matters or why it's great. It was his first No. 1 pop single. According to Ro, it was the first song since "Billie Jean" to hit No. 1 on pop, black, and dance charts simultaneously. It was the song that propelled his big breakthrough album, Purple Rain, to the big time. It's a dance song that lacks a bass line and is no weaker for it. It makes brilliant use of Prince's LinnDrum, with percussion that's spare and haunting.

"'When Doves Cry' is probably the most radical song of the first five years of the 1980s because there's no bass," Touré argues. "You don't strip down pop music. It's supposed to be full orchestration." And yet it works.

Oh, and by the way — doves can cry.

8) "Darling Nikki"

How sexy a song is "Darling Nikki"? So sexy that it sparked Tipper Gore and other political wives to form a new group devoted to making music less sexy:

Looking at the lyrics, it's not hard to see where Tipper might have objected:

I guess you could say she was a sex fiend

I met her in a hotel lobby

Masturbating with a magazine

The song isn't just explicit; it's, once again, centering on women's pleasure and sexual experiences, and celebrating for its subject her fearlessness and eagerness to own her own sexuality. Naturally, that was going to be challenged. "He offered 'Darling Nikki,'" Ro notes, "when television's most risqué show was Dynasty."

9) "Purple Rain"

Because he doesn't fit into the image of the Jimi Hendrix/Eric Clapton/Jimmy Page, hard-rock, hyper-adept technical musician, Prince's virtuosity at the guitar is sometimes neglected. But it's impossible to ignore in Purple Rain's nearly nine-minute title track, which follows up Prince's mournful regrets over his relationships with his father, his ex, and bandmates with a guitar solo of epic scale.

Nailing a guitar solo is tough; the genre lends itself to masturbatory self-indulgence and not toward carefully constructed melodies. But Prince nails it, providing a cathartic conclusion to the soundtrack. As Touré notes, the song likely had religious significance, as when Prince sings, "You say you want a leader, but you can't seem to make up your mind / I think you better close it / And let me guide you / To the Purple Rain." What's the rain? "Questlove tells me it's intended as a baptismal symbol," Touré writes. It's a small wonder that the song has become the defining track for Prince fans. It's him offering a path to salvation.

10) "Raspberry Beret"

Around the World in a Day, Prince's follow-up to Purple Rain, had a very unusual promotion strategy. According to Ro, he didn't let Warner Bros. run merchandising ("Any merchandising in the stores is stuff they've done on their own," Warner's Jeff Ayeroff said of Prince's management) or do much in the way of advertising. They didn't pick out songs to promote; they just sent copies to stations and let them "pick what they like."

But nearly a month after the album's release, Prince finally put out a real single: "Raspberry Beret," a fairly straightforward but deliriously catchy pop song that any halfway decent radio programmer would've picked from the track list anyway, about a virginal Prince picking up a girl with a sharp hat at a five-and-dime ("another great pornish story song," as Touré says). It would become one of his most-covered tracks, most notably by Hindu Love Gods (a band composed of Warren Zevon and the non-Michael Stipe members of REM).

11) "Kiss"

"Kiss" was the lead single of Parade, Prince's second soundtrack after Purple Rain, this one for his much-reviled directorial debut, Under the Cherry Moon. The album got a far better reception than the movie, not least due to "Kiss."

He initially wrote the song for Mazarati, a band in Prince's circle formed by former Revolution bassist Brownmark, but after the band stripped the song down into the minimalist form it would eventually take, he took it back; to appease them, he offered to credit them on it so they could get paid. It nearly didn't make it on the album after that ("Prince changed his mind about the song," Ro writes, "'Kiss' was too strange.") but after Prince flip-flopped again, it snuck on.

The song features some of the best elements of Prince's work to date: like "When Doves Cry," it lacks a bass line and sounds better for it; like "When You Were Mine" it's sung in falsetto that works without being distracting. And it keeps his approach to women's sexuality, experience, and power: "Women, not girls, rule my world."

12) "Sign o' the Times"

If Purple Rain is the album for which most people will remember Prince, Sign o' the Times was the critics' favorite, the sprawling double-album reflecting his ambition and political impulses. It won Prince the Pazz & Jop critics' poll both for the album as a whole and for its title track, which hit No. 3 on the pop charts despite being noticeably more somber than his usual dance tracks. It stands out as one of the earliest reactions by a prominent musician to the AIDS epidemic:

In France, a skinny man died of a big disease with a little name

By chance his girlfriend came across a needle and soon she did the same

The song also reflected Prince's increasing reliance on himself, and the technology to which he had direct access, in creating tracks. "Working with programmer Todd Harriman, Prince created almost all of the music using the groundbreaking Fairlight Synthesizer," AllMusic's Ed Hogan writes. Sign o' the Times was his first album since breaking with the Revolution, and it occasionally feels like a break-up record, albeit an unusually socially conscious one.

13) "I Could Never Take the Place of Your Man"

"When You Were Mine" is up there, but this is probably my personal favorite song of Prince's, the fourth single off of Sign o' the Times. The plot is simple: A woman Prince knows has been left by her man, and seeks comfort in Prince (who wouldn't?). Prince wants to help, but knows he and the woman don't belong together in the long run, and he also knows she wants more than a casual fling. It's typical Prince woman-centered sexual politics, turned slightly melancholic, as with the rest of the album.

But it's also just a damn good pop song, driven by a strong lead guitar/synth riff and a brilliant verse-to-chorus buildup, as distorted chords give way to an explosion of synths when the main refrain comes. It's songs like this that illustrate why Prince could never be pigeon-holed as dance music or R&B. He was a bona fide rock star, capable of tracks that wouldn't feel out of place on a Bruce Springsteen album.

14) "7"

Perhaps Prince's last major single, "7," came after a string of disappointments. His famous Black Album was scrapped at the last minute in favor of the underwhelming Lovesexy. Three more forgettable albums (including the soundtrack to Tim Burton's 1989 Batman movie) followed.

Then he titled an album after an un-pronounceable symbol, which he would later choose as his own name, meeting with critical adulation and including "7," an instantly iconic single that appropriately enough peaked at No. 7 on the Billboard Hot 100. The song's meaning is tough to decipher. It's certainly not a pornish story song, that's for sure. The predominant theories feature religion: maybe he's referencing the seven deadly sins, or the omnipresence of the number in the Book of Revelations, or referring to the seven major world religions.

Whatever the meaning, the martial tone and feeling of world-historic importance conveyed by the chorus were all Prince. He always excelled at making the apocalyptic dance-able without diminishing its import in any way, and "7" did that as well as any of his oeuvre.

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