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"I was very into Jack Kerouac, and I read a little book by Jack Kerouac called Tristessa, which was about a Mexican prostitute. And although the song's not about a Mexican prostitute, I thought it was such a cool title for a- I've always like girls' names in songs. Always been attracted to that. Um, like "Caroline, No", that kinda stuff. So um, I dunno, it's kinda vague. I think it's about an LSD trip, I'm not really sure.
What I like about Tristessa, in hindsight, is it's probably similar to Siva as- Siva & Tristessa probably more than any other 2 songs on Gish sort of point the way where the Pumpkins are headed, this very electric, kinetic style. The use of the guitar as almost like, as Eastern instruments, pulling on the strings, & taking them out of tune, & kind of playing with the harmonics of the guitars, & a lot of open strings, & that whatever, you know. People used to say, when they'd come see us live, they'd be like, "I can't believe there's only 2 guitars playing." Because the style we would play, it would almost sound like there were 3 guitars. And James & I really learned how to do a certain kind of technique that would sort of make the band sound bigger than the other bands that we might be playing on the bill on. So, Tristessa sorta captures that, that technique & that style. And uh, still play it live, still like the song, so- it must not be too bad." -BC, Matt Pinfield interview, Nov. 2011
"Lifted from author Jack Kerouac's book of the same name, written, I think, about a Spanish prostitute. I see myself not as a whore but as a mirrored reflection in the feminine creative mind. I will await the artist within to come out to play. I call out her name longingly, coyly. Maybe I know that the artist in me is indeed meant to be a whore? Our second single this was, re-recorded to try to clarify an earlier version. In the trade-off something vital gets lost. I won't even bother to try to make it better, a shrug of ambivalence. I have already moved on from her." -BC, Gish 2011 re-issue liner notes