In one scene in the movie, Andy (Luke Wilson) goes into a bar with a bicycle wheel, saying that someone had stolen the rest of his bike. Writer, Director, and co-star Bruce McCulloch once performed a skit on The Kids in the Hall (1988), where he played a man whose bicycle wheel had been stolen, but the rest of the bike had been left behind.
This was not screened for the critics and the due date was repeatedly pushed back until Bruce McCulloch's other directorial feature Superstar (1999) was being released.
In the scene where the personal ads are being read, they refer to the 5'1" man as having the saddest name in the world. The man's name is Owen, which is Luke Wilson's brother's name.
Several bits from The Kids in the Hall (1988) that McCulloch wrote were recycled for this film, a portion of a bike being stolen, an attempt to put a funny message on an answering machine that accidentally worked out, reading personal ads, et cetera.
The movie was originally scheduled to be shot in Toronto in June 1997, but filming was delayed and didn't begin until October 1997.