Jack Black
Role: Dan Landsman
James Marsden
Role: Oliver Lawless
Kathryn Hahn
Role: Stacey Landsman
Jeffrey Tambor
Role: Bill Shurmur
Kyle Bornheimer
Role: Randy
Henry Zebrowski
Role: Craig
Donna DuPlantier
Role: Taj
Denise Williamson
Role: Alyssa
Han Soto
Role: Dale Harkin
Dermot Mulroney
Role: Dermot Mulroney
Mariana Paola Vicente
Role: Hot Girl
Kendra Waldman
Role: Hotel Employee
Russell Posner
Role: Zach Landsman
Charlotte Gale
Role: Renina
Danielle Greenup
Role: Heather
Nicole Barré
Role: Holly James
Adria Tennor
Role: Classmate - Wendy
Terence Rosemore
Role: Employee #1 - Reggie
Liann Pattison
Role: Employee #2 - Lillian
Todd Blumenfeld
Role: Mulroney Guest
Jazzy Ellis
Role: Flight Attendant
Daniella Short
Role: Stripper #1
Cynyon Dawn Rodriguez
Role: Stripper #2
Joseph Lee Anderson
Role: Hollywood Bar Waiter
Reginal Varice
Role: Cab Driver
Adam Weinstein
Role: Kent Drazen
John-Paul Flaim
Role: Sports Talk Host
Eric Bickel
Role: Sports Talk Host
Jason Bishop
Role: Sports Talk Host
John Auville
Role: Sports Talk Host
Chris Angerdina
Role: Reunion Classmate (uncredited)
John L. Armijo
Role: Cab Driver (uncredited)
Jon Arthur
Role: Confused Airplane Passenger (uncredited)
James Howard Askin
Role: Reunion Classmate (uncredited)
Charles Barber
Role: Reunion Classmate (uncredited)
Tom Bui
Role: Upscale L.A. Restaurant Patron (uncredited)
Julia Caron
Role: LA Club Patron (uncredited)
Julio Castillo
Role: Reunion Classmate (uncredited)
David Michael Cefalu
Role: Reunion Classmate (uncredited)
Joseph Cintron
Role: Mike (uncredited)
Michelle DeVito
Role: Reunion Goer (uncredited)
Ryan Dewerth
Role: LA Club Patron (uncredited)
Neil Durr
Role: Class Reunion Guest (uncredited)
Steffie Grote
Role: Reunion Classmate (uncredited)
Sadarias Harrell
Role: Reunion Classmate (uncredited)
Ryan Hebert
Role: Classmate (uncredited)