Tom Ewing’s Top 100 Singles of the 90s

“Whenever I get dressed up, I feel / Like an ex-con trying to make good” Not coincidentally, the most ingratiating thing Bill Callahan’s ever done, and the most awkward. “Ex-Con” starts with Jim O’Rourke’s solitary and rueful trumpet, chopped and processed to sound almost like a synthpop line. It’s a sound with a creepy pathos – unlike certain alternative mopers, “Ex-Con”s protagonist doesn’t blame society for how he feels. Hell no, he’d love to fit in! It’s just that every time he steps out of his flat he turns into a stalker or a (paranoid!) android, his suit feels bad, his tie’s trying to strangle him, he’s looking at kids in the supermarket and making vague plans to snatch them….if a shy, shuffly character from a Dan Clowes strip made a record, “Ex-Con” would be it. Come to think of it, in a Dan Clowes strip “Ex-Con” would go to number one.

In our duller, kinder world, no chance, but you can still pick up the single if you look. And the chances are you’d like it whether or not you can empathise. The soundworld O’Rourke and Callahan put together for Smog’s masterful Red Apple Falls album is a thing of severe beauty. Bill’s spartan, sardonic phrasing picks its way through Jim’s haiku production, which turns each track into a temple where every note is sacred. In this context “Ex-Con” is party music, though it’s been put together with just as much care as the rest of the LP. I think it’s fragile, catchy, charming and sad. Every indie band that doesn’t just insult the public makes the bogus claim that their music is really ‘commercial’, people just don’t buy it. “Ex-Con” is one of those rare, self-sufficient records where that assertion comes out touching instead of irritating.