4: Cuban Boys, “Cognoscenti vs. Intelligentsia” (no.4, 1999)

For the simple reason that, as Lily Allen once sang, “It makes me smile.” A dark horse contender for the Christmas 1999/millennial number one, this may well stand as the novelty hit to end all novelty hits, seeking - for the simple reason nobody else had ever previously thought to do it - to substantiate a dial-up Internet sensation (singing animated rodents) with homemade beats, old Roger Miller outtakes, urban legends from the golden age of radio (“We’re off? Well, that ought to hold the little bastards”) and snatches of dialogue from any other TV or film enterprise that came to hand.

Any old hack could have put this out under the till-ringing title “The Hampster Dance” (as, indeed, EMI originally wanted to), but it takes a bold Situationist flourish to release it under the name of an obscure philosophical tract most singles buyers wouldn’t have been able to pronounce. Then again, the Cuban Boys - mad electronic scientists, and longtime John Peel favourites - were also bold enough to try mashing up South Park with unfashionable 70s combo Kenny’s dancefloor favourite “The Bump” for the yet-more-insane “Oh My God, They Killed Kenny”, by the end of which you may very well feel like a hamster spinning around in its wheel.

I can remember feeling hugely disappointed at the time, but in the end, maybe it’s for the best that “Cognoscenti vs. Intelligentsia” (the more you read it, the more inspired that title gets) got jostled out of the top spot by Westlife, John Lennon’s re-released “Imagine” (zzzzzzzzzzz) and Cliff’s awesomely bad “Millennium Prayer”, and instead had to settle for being number one in the Peel Festive 50: after all, singing hamsters are for life, and not just for Christmas. (Also hear: “The Golden Age of Video”, 2009’s copyright-shredding YouTube megamix in which pre-eminent Cuban Boy Ricardo Autobahn further bolstered his postmodern-pop credentials.)

5: White Town, “Your Woman” (no.1, 1997)

The thinking of most pop music is limited to the bedroom (or wherever else our musicians can or can’t get laid these days), but there’s a particular legend to be attached to those songs actually made there, on rudimentary recording equipment, probably held together by some form of sticky-backed plastic, by young men with heads full of ideas, a lot of kit and rather too much time on their hands. (See also, in this context: Daniel Bedingfield’s “Gotta Get Thru This”, Owl City’s recent “Fireflies”.)

“Your Woman” was Derby-based Jyoti Mishra’s big pop breakthrough after a couple of years noodling around on the indie scene. Inspired to try something different, Mishra tried a song from a perspective other than that of the typical lovelorn/lovesick male singer-songwriter - thus blurring the gender lines of an entire generation (as Boy George’s first appearance on Top of the Pops had fifteen years before) who were given pause to wonder whether the vocalist was gay, or a woman, or just a bloke reading a break-up note from a female lover. (Listening to “Your Woman” again, all these readings are possible.)

Over a decade on, the song itself sounds as fresh as ever, despite sampling its trumpet riff from an old Al Bowlly number (1932’s jaunty “My Woman”, if you’re interested), and despite having been fairly rigorously lifted from since, first by the producers of Alizee’s “Moi Lolita” (see no.16 in this list), then (rather horribly) by UK grime merchant Wiley for his recent hit “Never Be Your Woman”. Sidebar: is this the only song in chart history to namecheck Marxism in any form?

6: Annie, “Chewing Gum” (no.25, 2004)

Thank heavens for string theory. In a parallel universe - one where there is no such thing as N-Dubz, and none of us would have the misfortune of seeing Lady GaGa’s arse every five minutes - the Norwegian formerly known as Anne Lilia Berge Strand would be the biggest pop star on the face of the planet. In this alterna-universe, due notice would have been paid to her two fine albums, “Anniemal” and “Don’t Stop”, lovingly and shimmeringly compiled as they were with Richard X and the same Xenomania crew who’d been responsible for Girls Aloud’s numerous hits and the recent renaissance of all things Kylie; and “Chewing Gum”, the lead-off track from Annie’s first album, would have gone to number one forever.

Back in our miserable grey world, however, we’re left pondering the locked-room enigma of how the attractiveness of a female pop performer could actually come to count against her; and it’s true, I think, that the music industry came to think of Ms. Strand as just another passing, pre-packaged attraction: Holly Valance with a better developed sense of irony, say, where in fact, Annie’s work on record to date suggests she might well be the unlikely lovechild of Wallander and Siobhan Fahey from Bananarama. (Wallander for the undercurrent of Scandinavian melancholy that runs throughout her albums: Tore Kroknes, the DJ boyfriend with whom she first recorded, died suddenly of a heart defect in 2001, and his spirit presides over at least the first album.)

Of course, it doesn’t help when even your record company - in videos like the one above, or during appearances on Popworld - is marketing you as another interchangeable blonde clone, or licensing your best songs for use in mediocre-to-forgettable romcoms. (One of the few redeeming features of the Sex and the City sequel was its airing of the tremendous “Songs Remind Me of You” in the background of an Abu Dhabi nightclub scene.)

In a marketplace where any number of 80s copyists (La Roux, or the insufferably twee Ellie Goulding) have recently been forced down our throat, Annie may just have to content herself with being the connoisseur’s choice: the go-to girl for thinking pop kids with a sweet tooth. The perfectly angular and breathy “Chewing Gum”, which sounded as minty-fresh during the Glee pilot as it did upon the song’s original release, is as fine an introduction as any: a cautionary tale aimed at those men who come to think they’re indispensable when, in fact, once masticated, they’re every bit as likely to be spat out on the kerb. In other words, folks: chew it, wrap it, bin it. It’s a pity the industry keeps doing the same to Annie herself.

7: Gary Byrd and the GB Experience, “The Crown” (no.6, 1983)

An entire black history month squeezed into ten mouthwatering minutes, making it one of the longest records ever to chart in the UK. (No wonder there weren’t any follow-up hits: the GB Experience had worn themselves out on this one.) Self-appointed professor of ebonics Byrd here gives us not just the lowdown on the African people’s progress from mystical kingdoms and trading ships through to Roots and Jackie Robinson, but also several of my favourite couplets of all time: “You may have seen the Raiders from the Lost Ark [sic]/But you still left the theater in the dark”.

Indeed, part of “The Crown”’s project appears to be to redress an imbalance, putting in several hundred words for black history in the face of a popular culture becoming increasingly monopolised by white imagery (“It’s not Star Wars/It’s not Superman/It’s not the story of the Ku Klux Klan”). The joy is in hearing how this most serious of intentions could be framed by such a cracking tune: produced by Stevie Wonder (making this easily the best thing he ever did during the 1980s), with some very Chic basslines, it’s funky as all hell; you could put this on at the BNP disco, and Nick Griffin would get up and cut a rug. I owe my discovery of “The Crown” to Radio 2 sports newscaster Bob Ballard, which seems a terribly Caucasian sentence to write in the circumstances.