Quentin Tarantino had originally intended to include "My Sharona" (The Knack) on the soundtrack to Pulp Fiction (1994), but when he went to obtain the rights he found the song had already been licensed to this movie.
Director Ben Stiller cast Steve Zahn after seeing him perform on stage in New York City. Ethan Hawke was in the production with Zahn.
Screenwriter Helen Childress was 19 years old and a freshman at USC when she completed the script.
Ben Stiller was told he could include Lisa Loeb's "Stay" on the soundtrack only if he agreed to put "Baby, I Love Your Way" (remade by Big Mountain) on the soundtrack as well.
The psychic friend who Lelaina calls is voiced by Ben Stiller's real-life sister, Amy Stiller.
Dave Pirner, Soul Asylum front-man and boy-friend of Winona Ryder during that time, is visible in some of the "home-made" videos.
The scene in which Michael and Lelaina discuss the Big Gulp on the back of Michael's car was originally supposed to have the song "Beth" by 'KISS' playing. Ben Stiller couldn't secure the rights to the song so they opted for "Baby I Love Your Way" by Peter Frampton instead. Peter Frampton was an upstairs neighbor of Ben Stiller during filming of the movie.
Lisa Loeb's song, "Stay", was included on the soundtrack after Ben Stiller was given a tape of the song by Ethan Hawke, who was a personal friend of Loeb.
Original drafts of the script included a subplot involving Lelaina's alcoholic sister Patty, who was in rehab. A couple of those scenes were actually filmed but ended up getting cut. Patty was played by screenwriter Helen Childress' real-life sister, Patricia Childress.