Freddie Prinze Jr. as Ryan Dunne

Jessica Biel as Tenley Parrish

Fred Ward as Sean Dunne

Matthew Lillard as Billy Brubaker

Brian Dennehy as John Schiffner

Jason Gedrick as Mike Dunne

Brittany Murphy as Dede Mulligan

Bruce Davison as Rand Parrish

Marc Blucas as Miles Dalrymple

Wilmer Valderrama as Mickey Dominguez

Christian Kane as Dale Robin

Corey Pearson as Eric Van Leemer

Cedric Pendleton as Calvin Knight

Gabriel Mann as Auggie Mulligan

Zena Grey as Katie Parrish

Susan Gardner as Marjorie

Beverly D'Angelo as Lusty House Mother

Jed Rhein as Pete

Hank Aaron as Self

Thunderbird Dinwiddie as Lauren Hodges

Randi Layne as Victoria Parrish

Mark Robert Ellis as Umpire

Tim Lucason as Hyannis Batter

Tammy Arnold as Vassar Graduate

Nikki Griffin as Auggie's Girlfriend

Kelly Cole Childers as Baseball Fan

Jason Davis as Fischer the Valet

John C. McGinley as Hugh Alexander

Robert Harris as Baseball Fan