The #UncoolTwo50 is a simple exercise of daunting scope. Pick your 50 favourite singles from 1977 to 1999 (and then list them as part of the public challenge, which is happening on Bluesky from October 1st). I don’t know if these are the best ever 23 years for pop music, and I don’t know if they’re the years where I was most consumed by it – I’ve spent a lot of the time since writing and thinking about pop, after all.
But this is absolutely the formative era for me and pop music, which means not only am I trying to pick 50 records from an absurdly wide and deep pool, I’m also contesting with my younger self, and different versions of my younger self, and – because I revisited this period on Popular and repeatedly with the People’s Pop Polls – previous revisions of what I like.
It’s all too much! At one point my “shortlist” for this exercise had almost 600 songs on, and while some of those were tips of the hat to long-gone teenage editions of myself, never likely to trouble the actual scorers (hi there “Fool’s Gold”!), most weren’t. It was still a devil to wrestle them down.
I ended up with a list of 100 tracks. I could have filled it up entirely with play-it-at-my-funeral perennials, but after four years of pop polling some of those old favourites are having a well-earned rest. (The list of “seeds” – tracks likely to do well – for the challenge is a list of excellent songs I’m fine with not hearing again this decade). So it’s a mix of faithful friends and songs that jumped out of the longlist and sparked something, making me think – why not, eh?
The top 50 songs will run on my Bluesky account, but I’ll post them here when I get to them. This series of posts starts with the 50 that didn’t make it.
100. ICE CUBE – “It Was A Good Day” (1992)
A high-concept song, perfectly executed. Feels like an idea that was hanging around waiting for some rapper to do it – I definitely remember reading descriptions of “It Was A Good Day” long before I heard it which dwelled on its concept and punchline and missed the creamy ambiguity with which Ice Cube executes that stuff. Obviously it’s one of the definitive “this is how you turn a sample into a track” tunes too.
99. THE DISMEMBERMENT PLAN – “The Ice Of Boston” (1997)
The first band I only heard – or heard of – because of Pitchfork, who loved ‘em. More than I did, honestly. When I was an indie fan, the big attraction of the genre was finding a song which exactly matched whatever turmoil you were feeling at the time; in my teens and early 20s, this happened a lot. By my mid-20s, the trick was wearing off; there’s only so many records about miserable dudes a miserable dude can hear before he thinks, maybe taking steps to not be miserable is an option? I first heard “The Ice Of Boston” in the winter of 2000, living on my own in a mostly unfurnished and generally freezing flat, and it was one of the last times when the old “my life – it’s in this song!” impulses kicked in. Nothing else in these 100 tracks sounds much like it.
98. AMIRA – “My Desire (Dreem Teem Remix)” (1997 or 1998)
I found with the “Fear Of Music” challenge (50 singles from 2000-2023) that UK garage was a genre I knew I loved as a whole but pinning it down to specific singles proved really difficult (the same goes for drum & bass in this challenge, and honestly for most of dance music – singles-based genres which make most sense in the mix). “My Desire (Dreem Teem Remix)” gets at the lushness and sweetness of UK garage well enough though, and the deep lego-build pleasure of hearing 2-step rhythms interlock.
97. PET SHOP BOYS – “Can You Forgive Her?” (1993)
I decided on a one-song-per-artist rule in the Top 50, so there are a few duplicates lower down. This was one of the easier dilemmas, as [REDACTED] ultimately fit the shape of the list as it emerged a lot better, so “Can You Forgive Her?” was consigned to the lower end quite quickly. I think, with hindsight, this is the emergence of the Pet Shop Boys’ later style – you can’t imagine anything on Discography fitting onto, say, Hotspot, but you can see this doing so. Is that a good thing? I don’t know. This is a masterpiece, though, a song about the intolerable pressure of living in denial of who you actually are, an unusual subject for a genre in which confident self-expression tends to be a default.
96. SOPHIE B HAWKINS – “Damn, I Wish I Was Your Lover” (1992)
I didn’t intend this juxtaposition to work so well, but here’s more frustrated queer pop from a related but different angle – the agony of being in love with someone trapped in an abusive straight relationship. While “Can You Forgive Her?” is all about refusing pleasure, so its wordy structure and hammering riffs feel slightly ‘off’ as a functioning pop song, “Damn” absolutely demonstrates the liberation and bliss Hawkins is so desperately offering, with one of the most jubilant choruses of the era (“SHUCKS!”)
95. BONEY M – “Rasputin” (1978)
It’s easily overlooked what a total beast this is instrumentally – those drums! Had to be removed from the list 3 times and thrown into the Volga before it settled here, but there is disco to come.
94. GHOSTFACE KILLAH ft MARY J BLIGE – “All That I Got Is You” (1997)
Shameless weepie – there are lots of rap songs out there about loving your poor old mum but this one really hits home for me in a way the others don’t, maybe because Blige does such a beautiful turn giving the mothers’ perspective.
93. HOLE – “Malibu” (1998)
I heard “Celebrity Skin” in a club – well, a pub with people dancing in it – before finalising the list and thought “Wait! Have I made a terrible error?” (and then didn’t put “Malibu” in my Top 50 anyway). “Celebrity Skin” is the one likelier to do well in the overall challenge but the yearning and anger in “Malibu”, and the fact Courtney Love doing a broken-hearted power ballad is such a good idea, makes it the one for me.
92. DOUBLE TROUBLE ft THE REBEL MC – “Street Tuff” (1988)
YES. It’s the Rebel MC. When the list got down to about 200 I realised that it included basically every UK hit from the late 80s with any kind of hip-house element, because they’re all terrific. This is the British equivalent of Rob Base & DJ E-Z Rock’s “It Takes Two”, an unimpeachably joyful one-off which even rap sceptics (judging by the kids at my school) had no choice but to vibe to.
91. BROADCAST – “Echo’s Answer” (1999)
No other song on the list – and no other song I know, really – feels like this. It seems perverse that it was even a single, especially as this band could and did do extremely good singles that are also catchy pop songs not whatever radiophonic hauntology nursery rhyme is happening here. But that’s its beauty, asking you to imagine a sideways step into a mirror world where things like this are pop singles.
I may or may not get the next one of these up before the challenge officially starts on Monday night and I post the No.50 song, which I knew would be my first one the moment the challenge was announced.