Jennifer Aniston as Brooke Meyers

Vince Vaughn as Gary Grobowski

Joey Lauren Adams as Addie

Ann-Margret as Wendy Meyers

Jason Bateman as Riggleman

Judy Davis as Marilyn Dean

Vincent D'Onofrio as Dennis Grobowski

Jon Favreau as Johnny O

Cole Hauser as Lupus Grobowski

John Michael Higgins as Richard Meyers

Justin Long as Christopher

Ivan Sergei as Carson Wigham

Keir O'Donnell as Date (Paul)

Geoff Stults as Date (Mike)

Vernon Vaughn as Howard Meyers

Elaine Robinson as Carol Grobowski

Jane Alderman as Mrs. Grobowski

Jacqueline Williams as Shondra

Peter Billingsley as Andrew

Jane Hu as Diane

Rebecca Spence as Jen

Mary-Pat Green as Mischa

Tiffany L. Addison as Waitress

Jessica Vilchis as Hot Girl

Lisa Pace as Hot Girl

Samantha Albert as Debbie

Susan Messing as Tourist

Wayne A. Brown as Tourist

Maynard Love as Tourist

William Dick as Waiter

Jenna Hurt as Poker Girl

Jessica Stramer as Poker Girl

Ashley Giancola as Poker Girl

Lanae Sahs as Poker Girl

Sharon Vaughn as Boat Tourist

Nydia Rodriguez Terracina as Boat Tourist

Phil Ridarelli as Boat Tourist

Rhett Miller as Old 97's

Murry Hammond as Old 97's

Ken Bethea as Old 97's

Philip Peeples as Old 97's

Eric Bradley as Tone Ranger

Eduardo N. Martinez as Hot Dog Vendor

Chuck Stubbings as Country Clubber

Linda Cohn as ESPN Sportscaster (voice)

Arden Cho as VIP Party Guest (uncredited)

Mercedes Mason as Goblet Girl (uncredited)

Jennifer A. Goodman as Cubs Fan (uncredited)