Arye Gross as David Crown

Courteney Cox as Carrie Davenport

Kevin Pollak as Eli

Julie Brown as Zoe

Mitchell Ryan as Kenneth Davenport

Mitzi McCall as Freida Crown

B.J. Ward as Giselle Davenport

Philip Bruns as Irv Crown

Jack Carter as Rabbi

Tess Foltyn as Hanna

David DeCastro as Beer Vendor

Donald Brown as Crackerjack Vendor

Aaron Lustig as Movie Bully

Connie Sawyer as Waitress from Hell

Steven Brill as George / French TV Announcer

Davis Guggenheim as Pitcher

Craig Alan Edwards as 1st Baseman

Rob Youngblood as Adam

John DeMita as Chipper

Lisa Waltz as Lizbeth

Kimberlin Brown as Leeza

Kevin West as Tour Guide

Justin Shenkarow as Buddy

Mindy Mittleman as Cindy

Jensen Daggett as Cheerleader

Amanda Foreman as Waitress

Kimber Sissons as Tracy

Larry Poindexter as Carrie's Date

Frank Birney as Priest

Johnny Most as Basketball Announcer

Carrie "CeCe" Cline as Teenage Sunbather (uncredited)