Songfacts®:

• This song is about the novel of the same name by the American author Jack Kerouac. "Tristessa" is the name of the book's central character and is taken from the Spanish word for sadness, "tristeza."
  
  Kerouac is best known for On the Road, one the most important and culturally impactful novels in American history. He wrote 14 novels, with Tristessa generally not considered one of his major works.
  
  Tristessa (the book) takes place in Mexico in the mid-1950s. Like all Kerouac's novels, it's largely biographical, with only names and some details changed to obscure that fact and to protect identities. In the story, Kerouac tries to help a heroin-addicted prostitute. The events in the book aren't the driving force so much as the author's spiritual reflections and philosophical musings over the events. The spirituality of the book fits well with Pumpkins frontman Billy Corgan's explanation that Gish is "an album about spiritual ascension."
  
  It's a book about the tragic aspects of human existence. The story is reflected in the song's lyrics, though we don't know if Corgan was writing directly about the novel or using it as a window into something more personal.
• "Tristessa" was the second single Smashing Pumpkins released, following "I Am One." The "Tristessa" single included "La Dolly Vita" on the B-side, as well as "Honeyspider" on UK editions.
  
  Of the original single pressings, roughly 4,000 were pink, the rest were black, and around 100 were gray due to technical errors. Those 100 gray versions are collectors' items today.
  
  Following "Tristessa" (but probably mostly resulting from the success of "I Am One"), major record labels started jockeying for position to sign the Pumpkins. Caroline Records won out.