Emilio Estevez and Catherine O'Hara previously acted in films for which John Hughes wrote the story and screenplay. Estevez starred in The Breakfast Club (1985), and O'Hara co-starred in Home Alone (1990) and Home Alone 2: Lost in New York (1992).
Writer and director Steven Brill had previously written the screenplays for The Mighty Ducks (1992), D2: The Mighty Ducks (1994), and D3: The Mighty Ducks (1996), all of which starred Emilio Estevez.
Writer and director Steven Brill and Allen Covert had both previously acted in The Wedding Singer (1998) the year before this film's release.
Emilio Estevez and Reni Santoni had both previously appeared in movies alongside Ally Sheedy. Estevez co-starred with Sheedy in The Breakfast Club (1985) and St. Elmo's Fire (1985). Sheedy appeared with Santoni in Bad Boys (1983).