Tristessa

"Tristessa" is the second ever release by The Smashing Pumpkins, and their first, and only, release on Sub Pop. Sub Pop released it as their "Single of the Month". It was written by Billy Corgan and later re-recorded for their debut album, Gish. The title is a direct allusion to Jack Kerouac's 1960 novella of the same name. There were about 4,000 of the original 7" single pressed in pink vinyl, while the rest were pressed in black vinyl. A failure to change the wax color between pressings resulted in about 100 that were pressed in grey-colored wax. These are especially rare and have sold for several hundred dollars apiece.

Following the release of "Tristessa", the Smashing Pumpkins were targets of a bidding war by multiple record labels, and ended up signing to Caroline Records. Unlike "I Am One", which was also re-recorded for Gish, "Tristessa" did not receive a second single release, and neither version of the song appears on the 2001 greatest hits collection, Rotten Apples.

Background
Corgan got the title from a Jack Kerouac book someone had given him that was written about a Mexican prostitute. Corgan said he loved the idea of a girl named Tristessa.

In a 2020 Instagram video, Corgan said that while he loves the guitar tones on the song, he never thought much of the composition compared to the other tracks. He as far as to say that it's the song he regrets the most, and felt later songs such as "Drown" would have been a better fit.

The song was written in around 2 to 3 days, and was performed live before releasing it as a single on Sub Pop. The Gish re-recording "brought no improvement on arrangement" and was "complete insanity", but that he's grateful helped build such a successful record.

Critical reception
CMJ called it "a grinding, drawled-out, lascivious rocker with a chisel-sharp pop aesthetic". The Chicago Sun-Times said it was an "epic rocker". In 2007, Spinner wrote, "a decade after the onset of diminishing returns, 'Tristessa' remains an absolute monster".