50. The Greatest Romance Ever Sold (1999)

By the end of the 90s, Prince obviously wanted commercial success again. The album Rave Un2 The Joy Fantastic came packed with guest appearances; the smooth hip-hop-soul balladry of The Greatest Romance Ever Sold was a good indication of its musical style. It wasn’t a bad song, but the sense Prince was following trends rather than going his own way was hard to avoid.

49. Letitgo (1994)

By 1994, Prince was more interested in fighting with his record company than the quality of his releases. Come was evidently thrown together to fulfill his contract. But even when he didn’t really care, he couldn’t turn his talent off completely. Letitgo isn’t a classic, but nor is it a disaster. Perhaps he made more of an effort because it’s about his desire to leave the Warners label.

48. U Make My Sun Shine (2000)

Prince hadn’t lost his ability to spot talent: U Make My Sun Shine featured a great guest appearance from neo-soul singer Angie Stone. Her presence seemed to rouse him – it’s a gospel/southern soul-inspired ballad, and a minor gem.

47. Dinner With Delores (1996)

Another thrown-together contractual-obligation album, Chaos and Disorder had a rough charm and immediacy, as evidenced by Dinner With Dolores, a sweet, if slight, song cut from the same pop-rock cloth as Manic Monday.

46. Gold (1995)

A lost nugget from 1995’s The Gold Experience, Gold reiterates the anti-materialistic message of 1992’s Money Don’t Matter 2 Night. It’s not groundbreaking in the way Prince’s singles once were, but it’s exquisitely written.

45. Batdance (1989)

The Batman soundtrack was the first real artistic wobble in Prince’s career, arriving replete with filler, including the phoned-in ballad The Arms of Orion. Nor has its largely instrumental first single dated well: it picks up when the vocals come in, but Prince had made umpteen more creative 12in remixes than this.

44. The Work Pt 1 (2001)

Beloved of Prince diehards, a bit of a schlep for everyone else, the jazz and Jehovah concept album The Rainbow Children underlined that Prince was now more interested in stubborn self-indulgence than commercial success. But it did yield The Work, a relentless, horn-laden James Brown-ish groove that unexpectedly collapses into slowed-down vocals and synth-y ambience.

43. Cinnamon Girl (2004)

Musicology was Prince’s biggest-selling album in more than a decade. It helped that copies given away with gig tickets counted as sales, but so did the presence of straightforwardly enjoyable songs such as Cinnamon Girl, which you could have imagined him writing circa Around the World in a Day.

Prince on the Purple Rain tour. Photograph: Ebet Roberts/Redferns

42. I Hate U (1995)

The Gold Experience was a better album than its relatively lukewarm reception suggested. I Hate You is The Most Beautiful Girl In The World’s evil twin: more pillow-soft soul, this time attacking rather than hymning a woman, complete with a faintly problematic faux-courtroom scene.

41. The Truth (1997)

An interesting single from Prince’s artistically lean years, primarily because it took him somewhere new. Stark, acoustic and blues-influenced, performed solo and boasting a great vocal performance, The Truth didn’t sound like any Prince single before it.

40. Thieves in the Temple (1990)

Prince clearly intended Graffiti Bridge to have a similar impact to Purple Rain, but the film was abysmal and the accompanying soundtrack uneven. Its lead single isn’t a bad song by any means – its sound is slinky and luscious, the chorus is great – but it’s no When Doves Cry.

39. Delirious (1983)

In the best possible way, the 1999 album was the sound of a man showing off: name a musical style and he could bend it to his own ends. Hence the US-only Delirious, a kind of dry-run for Let’s Go Crazy, with its roots in 50s rock’n’roll.

38. Why You Wanna Treat Me So Bad? (1979)

One aspect of Prince’s genius lay in his inability to be confined by musical genres. Early on in his career, Why You Wanna Treat Me So Bad? offered dancefloor-focused R&B that was influenced by both AOR and the emergent new wave, and concluded with a startling display of guitar pyrotechnics.

37. Soft and Wet (1978)

Released at the height of disco, Soft and Wet’s skeletal, off-kilter synth funk – complete with jazzy inflections – sounded like it came from another planet to the rest of the US chart. A minor hit, it quietly announced the arrival of a unique and uniquely unbiddable talent, so obsessed with sex he mentions his penis in the opening line.

36. Let’s Work (1981)

It’s all about the 12in mix. Not content with merely extending an album track for the dancefloor, Prince went to town, completely overhauling Let’s Work, interpolating sections of Controversy’s title track and Annie Christian, enhancing the song’s sweaty urgency with new vocals and keyboards, demonstrating a meticulous attention to detail where lesser artists would have expended no effort at all.

35. The Most Beautiful Girl in the World (1994)

It is incredible that The Most Beautiful Girl in The World is Prince’s only UK No 1, given the singles that preceded it. Nevertheless, it’s a deft homage to the super-soft 70s soul of the Delfonics and the Stylistics, both of whom he subsequently covered.

34. 7 (1992)

If you want evidence of Prince’s unique, almost mystical, abilities, 7 is an intriguing place to start. At heart, the song is a rousing acoustic campfire singalong with lyrics of a spiritual bent, albeit a fairly baffling one. Deeply unpromising on paper, he somehow makes it work to striking effect, spooning on the harmonies and vintage sitar effects.

33. Black Sweat (2006)

The problem with Prince’s wilderness years wasn’t a decline in talent, but a fatal lack of focus. The minimal funk of Kiss reimagined for the 00s, Black Sweat was evidence that Prince was marshalling his abilities once more. It wasn’t up to his 80s standards, but it was close enough to pass muster.

32. Screwdriver (2013)

Later included on Hit n Run Phase Two, Screwdriver is the rawest single of Prince’s career, its overloaded, ragged sound verging on garage rock, or at least Prince’s take on the genre. In fact, your average garage-rock band couldn’t reel off remarkable solos the way he does throughout.

31. U Got the Look (1987)

Of all the artists on whom Prince bestowed his star-making qualities, the least likely was Scottish MOR singer Sheena Easton, recast on U Got the Look as a snarling sexual predator. The song itself is a little lumpy by Prince’s 80s standards, but not without a weird charm, embodied by its fake sportscaster announcements: “Boy v girl in the World Series of love”.

30. I Wish U Heaven (1988)

Prince was fond of describing Lovesexy as a gospel album, but that’s not a term you would use to describes the music on I Wish U Heaven: a thumping, tom-tom heavy beat, thick, chugging guitars, Prince’s vocal floating beatifically above in a cloud of electronics. The lyrics could be about God, or a lover. Either way, it’s a strange and lovely single.

29. America (1985)

Another single arguably best heard in its 12in version, which in America’s case lasts for nearly 22 minutes of frantic, paranoid acid funk, Hendrix-y soloing and claustrophobic harmonies. The darkness of Vietnam-damaged late-60s US psych recast for the Reagan years.

28. Dirty Mind (1980)

Startling, audacious and filthy from soup to nuts, the Dirty Mind album was Prince’s first masterpiece. Its melding of funk and rock and gleeful nose-thumbing at pop’s standard racial boundaries was Sly Stone-esque, but updated for the 80s. The razor-sharp robot funk of its title track was the perfect calling card: no one else sounded like this.

27. My Name Is Prince (1992)

The grip he had once exerted over the public slipping, you can see why Prince felt the need to reassert his authority in 1992. My Name Is Prince did it in style. Its intro listed his hits, its lyric switched between proclaiming himself divinely chosen and fretting about judgment day, and its music dealt in heavy breakbeats and noise that suggested he had been listening to Public Enemy.

26. Take Me With U (1985)

The influence of musical consiglieres Wendy Melvoin and Lisa Coleman started drawing Prince towards the sound of 60s psychedelia on the Purple Rain soundtrack. You can hear the first signs on Take Me With U, a gorgeous, carefree song enveloped by a groggy string arrangement – written by Coleman – that never quite drifts in the direction you expect.

25. Guitar (2007)

Planet Earth wasn’t the best of his latterday albums, but its standout track was among his best his latterday singles, an infectious glam stomp with a typically witty kiss-off lyric: “I love you baby and I wish you well, I’ll write you a letter when I learn how to spell”.

24. I Could Never Take the Place of Your Man (1987)

A return to the pop-rock territory of Little Red Corvette and 1980’s When You Were Mine, I Could Never Take the Place Of Your Man is straightforward compared with a lot of the material on Sign o’ the Times, its lyrical conceit notwithstanding, but it’s a perfect example of Prince’s songwriting craft.

23. Gotta Stop (Messin’ About) (1981)

Perhaps only Prince in 1981 would think a song about voyeurism and compulsive masturbation was just the thing to break him in the UK. Never released as a single in the US, it unsurprisingly wasn’t a hit, but that’s no reflection on its thrilling, wildly idiosyncratic staccato funk.

22. I Would Die For U (1984)

More personal myth-making – “I’m not a woman, I’m not a man, I am something that you’ll never understand” – on a single where the indelible chorus masks a genuinely odd production: an unsettling stop-start rhythm that precludes dancing; rattling, incessant hi-hat perplexingly loud in the mix. Still, he knew what he was doing – it worked.

21. Money Don’t Matter 2 Night (1992)

Co-written with Rosie Gaines, its commercial chances in the US scuppered by a Spike Lee-directed video that MTV deemed too political and refused to show, Money Don’t Matter 2 Night is a fantastic song, the smoothness of its sound and delivery masking a punchy, politically engaged lyric that takes in both consumerism and Operation Desert Storm.

Prince in 1997. Photograph: Rick Diamond/Getty Images

20. Controversy (1981)

Effectively early 80s Prince’s manifesto – “I wish there was no black and white, I wish there were no rules” – Controversy also addressed the furore caused by Dirty Mind’s songs about troilism and incest with a blithe shrug and featured a bit of the Lord’s Prayer for good measure. The music, meanwhile, is awesome: tight, funky, fluently melodic.

19. Girls & Boys (1986)

Bafflingly unreleased as a single in the US, much to chagrin of some members of the Revolution, Girls and Boys returned Prince to appealingly tough funk, albeit decorated with weird production flourishes – honking duck-call synths – and lyrics that spike the mood of sultry eroticism with wit: “She had the cutest ass he’d ever seen – but he did too, they were meant to be”.

18. Cream (1991)

T Rex never broke the US, but Prince was clearly a fan and never more so than on this glorious, loving homage to Get It On, complete with lyrical echoes (the object of Prince’s affections is “filthy-cute” as opposed to “dirty-sweet”). Never given to underestimating his own importance, Marc Bolan would doubtless have adored it.

17. Baltimore (2015)

Prince’s death came amid suggestions he was in the grip of another artistic renaissance. Baltimore was strong evidence: inspired by Black Lives Matter, lyrically angry and confrontational in a way that was unlike his previous political work, it was also blessed with an elegant melody and striking string arrangement.

16. Pop Life (1985)

The brand of psychedelia found on 1985’s Around The World In A Day never sounded retro or like a pastiche. For all Pop Life’s backwards tapes and melodic nods in the direction of the Beatles, it was resolutely a product of the mid-80s, more evidence of Prince’s ability to not merely absorb influences but recast them in his own image.

15 Let’s Go Crazy (1984)

The emotional flipside of the eerie, troubled When Doves Cry, Let’s Go Crazy can barely contain itself. One of the greatest intros of the 80s – “Dearly beloved …” – leads into a relentless rhythmic clatter, explosions of metal guitar, raw-throated exhortations to party and utterly bizarre lyrics: “Let’s look for the purple banana”; “Pills and thrills and daffodils can kill”. A joy from start to finish.

14. Head (1980)

The sound of a libido gone berserk, Head is both irresistible and insane, a falsetto-voiced song about – wait for it – a virginal bride-to-be en route to her wedding, who bumps into Prince and is overwhelmed by the desire to fellate him. It should be ridiculous, but its raw funk groove is utterly compelling; Prince’s alchemical powers in full effect.

13. Alphabet St (1988)

1988’s Lovesexy was received coolly on release, which tells you more about the standard of the Prince albums that preceded it than its quality. In reality, it’s the last unequivocally superb album he made, while its lead single is a delight: an explosion of stop-start funk, popping bass and – in its full-length version – rapping from his new female foil Cat Glover.

12. Little Red Corvette (1983)

Prince at his most unrepentantly commercial. If MTV and US rock radio wouldn’t play black soul artists, then here was a black soul artist who could make pop-rock singles of a calibre they couldn’t ignore. It was his biggest hit to date, censors apparently missing a reference to its heroine’s pocketful of condoms (“some of them used”) in the second verse.

Prince in 1990. Photograph: David Brewster/AP

11. Sexy MF (1992)

Boasting the kind of lyric his subsequent conversion to the Jehovah’s Witnesses would preclude, Sexy MF offers up a JB’s-ish groove that’s simultaneously raw and tightly controlled, a chorus punctuated by the kind of lip-smacking noise also featured on Kiss and its author on superb priapic form: “I got wet dreams comin’ out my ears!”

10. If I Was Your Girlfriend (1987)

A dark, sparse crawl of a song, alternately sexy, pained and weirdly unsettling, If I Was Your Girlfriend played with ideas of gender (the androgynous sped-up vocal was credited to his female alter-ego Camille, a name under which he initially intended to release a whole album) that are commonplace now, but were uncharted territory for mainstream black music 30 years ago.

9. I Wanna Be Your Lover (1979)

Prince’s first truly spectacular single – and first US hit – I Wanna Be Your Lover was a fabulous, effortless-sounding song. The sound bore the influence of Chic in its scratchy, Nile Rodgers-ish guitar, while its synth-heavy arrangement presciently suggested what the post-disco future would sound like.

8. Mountains (1986)

A last outing for Prince’s unique contemporary take on psychedelia: an addictive, dizzying wash of sound – rumbling drums (possibly influenced by Kate Bush’s Running Up That Hill), synths, brass, rolling piano – topped with a falsetto vocal. The horn breakdown 30 seconds from the end is particularly glorious.

7. Sign o’ the Times (1987)

Prince fired his backing band the Revolution during the making of Sign o’ the Times: a bad move in retrospect, but initially at least his genius seemed unaffected. The title track is brilliantly stark: Aids, the Challenger space shuttle disaster and the crack epidemic co-mingled in a bleak state-of-the-nation address. If Prince was the Sly Stone of the 80s, this was his There’s a Riot Goin’ On.

6. Purple Rain (1984)

Originally a 10-minute-long country and western song intended for Stevie Nicks (who found it “too much”), Purple Rain was transformed into an epic power ballad during a six-hour rehearsal and recorded onstage at Minneapolis’ First Avenue club to astonishing, heart-stopping effect. Its elegiac tone makes it fitting that it was the last song Prince played live.

Prince at Hop Farm festival in 2011. Photograph: Neil Lupin/Redferns

5. 1999 (1982)

1999 is so familiar, it’s easy to forget what a weird idea for a hit single it was: a party-starting P-Funk-y anthem about a vision of imminent apocalypse. Perhaps its lyrics chimed with the fear and paranoia engendered by the escalating cold war. More likely, it was a huge crossover smash because it’s an incredible, impossibly assured piece of music.

4. Gett Off (1991)

Prince’s early 90s albums were nowhere near as consistent as his 80s work, but initially at least, he could still be relied upon to come up with stunning singles. From its opening scream to its ferocious concluding guitar solo, Gett Off is prime-quality Prince: funny, lubricious, preposterously funky, every bit the equal of his best work.

3. Raspberry Beret (1985)

Compared with everything else happening in pop in the nadir year of 1985, Raspberry Beret was in a different league. It represented the pinnacle of Prince’s psychedelic phase: another of Coleman’s superbly woozy string arrangements, a song so perfect and simple it had a kind of instant familiarity, as if you had known it for years on first listen.

2. Kiss (1986)

By 1986, Prince was peerless, so far ahead of everyone else in contemporary pop it was almost laughable. Kiss was all the evidence you needed. It repeated When Doves Cry’s hugely impressive trick of conjuring up funk without a bassline, and added perhaps the most indelible chorus of his career and a vocal that turns into an astonishing lust-racked scream at 3min 20sec.

1. When Doves Cry (1984)

Again, the familiarity of Prince’s most famous song tends to obscure what an audacious and daring piece of music it is. Everyone knows that funk is utterly rooted in the drums and the bass. When Doves Cry – the biggest-selling single of 1984 – insouciantly turns that on its head. It originally had a bassline, but Prince thought it sounded “too conventional” and removed it, leaving only a sparse framework of drums and synth. For a song that inexorably propels people to the dancefloor – whether at a hip club or a wedding reception – it’s remarkably downcast. Played in an minor key, its lyrics are alternately desolate, soul-searching and just weird: “Animals strike curious poses”. Experimental but multi-million-selling, it’s a work of era-transcending genius.