Not Fade Away 1987: Sign O' The Times, by Prince

Mind the gap. We've jumped from pop's patron saint of sexual frustration to its imp of polymorphous perversity. Now that's a segue.

On the whole the difference between the Smiths and this week's choice is that Prince's music said nothing to me about my life. But I guess that's what I loved about it. In 1987 no one - not even Morrissey and Marr if I'm truly honest (though it's a close-run thing) - thrilled me as much as Prince. He offered a vision of pop that was excessive, strange and, yes, downright kinky.

Set aside hip hop, and you could argue that Prince was the alpha and omega of American pop music in the 1980s. He took all his influences - Little Richard, Hendrix, Sly and the Family Stone, the Beatles - and made them fuel for his own rewriting of black music.

Not that he would ever limit himself in such a way. Prince was colour-blind when it came to music. He'd play anything, take on any form, any genre and shape it to his own ends.

He could rock out (The Cross), strip things back (Kiss), paint in primary colours (U Got the Look) or keep it monotone (Sign O' the Times is the best example, but When Doves Cry might qualify too).

At the same time he was following very obvious black precedents - most notably Al Green and Marvin Gaye - in the way he fused sensuality and spirituality. In Prince's world sex equalled love equalled God. Or vice versa. Presumably Madonna had been listening when she came to write Like a Prayer.

The God bit I could do without myself. And thinking about this I realise that I probably know less about Prince Rogers Nelson than almost anyone else in this list (with the exception of Augustus Pablo). But I don't feel I'm missing out on anything. For me Prince was never about biography. He was about fantasy. It didn't take much listening to imagine he had issues with his father, but really what fascinated was the libidinous world he luxuriated in and the ludicrously easy facility he had with music.

In 1987 he was at his most casually brilliant (and given how casually brilliant he'd been in the years before that's quite a claim). It was a cliché even at the time that if the double album Sign O' The Times had been a single disc it would have been up there with all those records that keep getting name-checked as the greatest of all time.

But maybe we need to see Prince in terms of his prolificacy. That he needed to be constantly creating, constantly recording, to get to where he wanted. To get to where we wanted him to be.

And Sign O' The Times is still rich with great songs. Even the one with Sheena Easton on it. But the two that stand out are the title track and If I Was Your Girlfriend.

The latter sees Prince's obsession with sexuality come to a head (ahem). It's the story of a man imagining being his girlfriend's female friend and what that could entail. As such it's part sex fantasy, part interrogation of gender, couched in a slow fug of funk. It was too wayward, too sexually ambivalent for an American audience and didn't chart in the US at all.

In its wake Prince's loverman persona was always much more macho in expression (think of Get Off and Sexy MF).

I should choose If I Was Your Girlfriend for that very reason, for its daring, its libidinal openness. But then I hear Sign O' The Times, and my ears start to burn. It still sounds like the most potent thing Prince ever did.

I guess it's a protest song about the state of the world. It seems to rail against drugs and gangs and the Aids virus and nuclear destruction and the explosion of the space shuttle Challenger, though you're never really clear who Prince is blaming for all this (and from the recorded evidence Prince is, if anything, something of a conservative politically). Dorian Lynskey argues in his book 33 Revolutions: A History of Protest Songs, that the track is "hopelessly toothless and noncommittal as a protest song", but he adds, "brilliant as a pop record".

And that's what I love about it. The sound of it, the way Prince bites down on the word "Crack" (which always makes me think of how the sound surges on Family Affair on the word burn), the stripped-down Sly Stone funk it uses to carry the words, the way it dissolves into a vision of love and marriage and parenthood "we'll call him Nate … if it's a boy").

In the end I guess this is as close as Prince came to engaging with the real world. You can attack him, I suppose, for the evasive way he did it. But you can't complain about the sounds he conjured up in doing so. Prince has always lived in his own head and not in the real world. Sometimes that seems like the better place to be.

Other Contenders

If I Was Your Girlfriend, Prince

Last Night I Dreamt Somebody Loved Me, The Smiths

I Won't Share You, The Smiths

Rent, Pet Shop Boys

King's Cross, Pet Shop Boys

Paid in Full, Erik B & Rakim

Fairytale of New York, The Pogues featuring Kirsty MacColl

True Faith, New Order

Pump Up the Volume, M/A/R/R/S

Brilliant Disguise, Bruce Springsteen

I Could Never Take the Place of Your Man, Prince

Death of a Disco Dancer, The Smiths

Big Decision, That Petrol Emotion

What Have I Done To Deserve This?, Pet Shop Boys & Dusty Springfield

Boops (Here to Go), Sly & Robbie

Birthday, The Sugarcubes

NME Single of the Year: Sign O The Times, Prince

John Peel's Festive 50 winner: Birthday, The Sugarcubes

And the best-selling single of 1987: Never Gonna Give You Up, Rick Astley