This was Charlie Korsmo's first on-screen appearance since Hook ou la Revanche du capitaine Crochet (1991). He was attending MIT when he was offered the role.
Melissa Joan Hart was in the middle of filming the 2nd season of Sabrina, l'apprentie sorcière (1996) at the same time. She took B12 vitamins to stay energized during the all-night shoots. Jennifer Love Hewitt was skeptical when Hart offered them to her, because she was convinced they were drugs.
Deborah Kaplan and Harry Elfont wrote the role of Kenny Fisher with Breckin Meyer in mind. Because of scheduling conflicts filming Studio 54 (1998), Meyer had to turn the role down. He took a smaller, uncredited role as Lead Singer of Loveburger. The role of Kenny Fisher went to Seth Green.
The fraternity on Trip McNeely's polo shirt is Delta Iota Kappa ("DIK").
Breckin Meyer: as the Lead Singer of Loveburger. Meyer and co-writer/co-director Deborah Kaplan later married in real life.
Melissa Joan Hart: as the Yearbook Girl. This role is her theatrical film debut, although she was already well known for her roles on television, on which she had been acting for thirteen years up to that point.
Jenna Elfman: as "Angel" the exotic dancer i.e. stripper, who cites herself as a dancer. In real life, Elfman is a classically-trained ballet dancer, although she does not dance in this movie.
Jerry O'Connell: as Trip McNeely, the high school's Big Man on Campus of a previous graduating class.