The movie was actually shot and completed in 1998.
Shannon Elizabeth filmed this before American Pie (1999) though it was released after that film. After filming this she got breast implants before being cast in American Pie. That's why there is a noticeable difference in her breast size in both movies.
All three male leads, Sean Astin, Matthew Lillard, and Brian Dennehy have starred in movies with Burt Reynolds. One of Denney's first movies was Semi-Tough (1977) starring Burt Reynolds. Sean Astin not only starred along side the bandit but was directed by him in The Last Producer (2000), which was re-titled as The Final Hit for home video release. And of course Matthew Lillard shared the screen with the legendary Reynolds in Without a Paddle (2004).
This is the first time Sean Astin and Matthew Lillard worked together. They also starred in the romcom What Love Is (2007). Astin was also in 2 episodes of Scooby-Doo and Guess Who? (2019), for which Lillard provided the voice of Shaggy Rogers among other characters.