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Jennifer Aniston
Brooke Meyers

Vince Vaughn
Gary Grobowski

Joey Lauren Adams
Addie

Ann-Margret
Wendy Meyers

Jason Bateman
Riggleman

Judy Davis
Marilyn Dean

Vincent D'Onofrio
Dennis Grobowski

Jon Favreau
Johnny O

Cole Hauser
Lupus Grobowski

John Michael Higgins
Richard Meyers

Justin Long
Christopher

Ivan Sergei
Carson Wigham

Keir O'Donnell
Date (Paul)

Geoff Stults
Date (Mike)

Jane Alderman
Mrs. Grobowski

Jacqueline Williams
Shondra

Peter Billingsley
Andrew

Jane Hu
Diane

Rebecca Spence
Jen

Mary-Pat Green
Mischa

Jessica Vilchis
Hot Girl

Lisa Pace
Hot Girl

Samantha Albert
Debbie

Jessica Stramer
Poker Girl

Ashley Giancola
Poker Girl

Lanae Sahs
Poker Girl

Sharon Vaughn
Boat Tourist

Nydia Rodriguez Terracina
Boat Tourist

Phil Ridarelli
Boat Tourist

Rhett Miller
Old 97's

Murry Hammond
Old 97's

Ken Bethea
Old 97's

Philip Peeples
Old 97's

Eric Bradley
Tone Ranger

Eduardo N. Martinez
Hot Dog Vendor

Chuck Stubbings
Country Clubber

Linda Cohn
ESPN Sportscaster (voice)

Arden Cho
VIP Party Guest (uncredited)

Mercedes Mason
Goblet Girl (uncredited)