Matthew Modine as Dave Goldman

Randy Quaid as Vic Damico

Paul Reiser as Donny Carson

Janeane Garofalo as Lucille

Amy Brenneman as Susan

Eliza Dushku as Emma

Ed Flanders as Walter Sims

Maria Pitillo as Kim

Lindsay Crouse as Grace Damico

Ross Malinger as Ben

Johnny Whitworth as Max Cooper

Wendell Pierce as Hector

Cameron Boyd as Jed Damico

Mae Whitman as Michele

Amber Benson as Meg Damico

Rob Reiner as Dr. David Townsend

Danny Masterson as Mikey

Jack Black as DJ at Party

Jayne Brook as Claire

Dana Wheeler-Nicholson as Heidi

Pamela Dillman as Sheila

Brad Hall as Phil

James Arone as Waiter in Italian Restaurant

Karlie M. Gavino Brown as Lindsay

Kirstie R. Gavino Brown as Lindsay

Marguerite Weisman as Sarah

Max Ornstein as Ring Bearer at Wedding

Dean Williams as Wedding Photographer

Caroline Lagerfelt as Mother #1 at McDonalds

Christopher Curry as Dad #1 at McDonalds

Dan Weisman as Boy at McDonalds

Stephanie Shroyer as Mother #2 at McDonalds

Michael Bofshever as Dad #2 at McDonalds

Christina Massari as Girl at McDonalds

Brian Frank as Screener

Shang Forbes as Engineer

T.K. Meehan as T-Ball Coach

Mina Kolb as Dorothy

Stephen Root as Awakened Neighbor

Woody Woodhall as Gerald

Michael Spound as Mike

Joe Basile as Father #1 at Dad's Day Out

Dennis Bowen as Grandfather

Kate Williamson as Grandmother

Nicholas Davey as Heidi's Son

Justin Garms as Sheila's son

Lauren Kopit as Sheila's Daughter

Keaton Simons as Party Dude

Juney Smith as Security Guard

Ellen Bry as Debbie

Christina Laskay as Kelly