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Kate Beckinsale

Donna Newman

Terry Crews

Singing Driver (uncredited)

Sean Astin

Bill

Rob Schneider

Prince Habeeboo (uncredited)

Cameron Monaghan

Kevin O'Doyle

Jennifer Coolidge

Janine

Christopher Walken

Morty

Jen Johnson

Bikini Girl (uncredited)

Jonah Hill

Ben at 17 years old

Katie Cassidy

Samantha at 27 years old

David Hasselhoff

Ammer

James Earl Jones

Narrator of Michael's Past (voice) (uncredited)

Henry Winkler

Ted

Julie Kavner

Trudy

Jorge Garcia

Ammer in SAP scene (uncredited)

Carolyn Hennesy

Kathy O'Doyle

Rachel Dratch

Alice / Alan

Dolores O'Riordan

Singer

Nick Swardson

Bed, Bath & Beyond Guy

Blake Clark

Roy (uncredited)