Jack Black as Dan Landsman

James Marsden as Oliver Lawless

Kathryn Hahn as Stacey Landsman

Jeffrey Tambor as Bill Shurmur

Mike White as Jerry

Kyle Bornheimer as Randy

Henry Zebrowski as Craig

Corrina Lyons as Lucy

Donna DuPlantier as Taj

Denise Williamson as Alyssa

Han Soto as Dale Harkin

Dermot Mulroney as Dermot Mulroney

Mariana Paola Vicente as Hot Girl

Kendra Waldman as Hotel Employee

Russell Posner as Zach Landsman

Charlotte Gale as Renina

Danielle Greenup as Heather

Nicole Barré as Holly James

Adria Tennor as Classmate - Wendy

J.T. Rowland as Steve

Terence Rosemore as Employee #1 - Reggie

Liann Pattison as Employee #2 - Lillian

Todd Blumenfeld as Mulroney Guest

Jazzy Ellis as Flight Attendant

Daniella Short as Stripper #1

Cynyon Dawn Rodriguez as Stripper #2

Joseph Lee Anderson as Hollywood Bar Waiter

Reginal Varice as Cab Driver

Adam Weinstein as Kent Drazen

John-Paul Flaim as Sports Talk Host

Eric Bickel as Sports Talk Host

Jason Bishop as Sports Talk Host

John Auville as Sports Talk Host

Chris Angerdina as Reunion Classmate (uncredited)

John L. Armijo as Cab Driver (uncredited)

Jon Arthur as Confused Airplane Passenger (uncredited)

James Howard Askin as Reunion Classmate (uncredited)

Charles Barber as Reunion Classmate (uncredited)

Tom Bui as Upscale L.A. Restaurant Patron (uncredited)

Julia Caron as LA Club Patron (uncredited)

Julio Castillo as Reunion Classmate (uncredited)

David Michael Cefalu as Reunion Classmate (uncredited)

Joseph Cintron as Mike (uncredited)

Michelle DeVito as Reunion Goer (uncredited)

Ryan Dewerth as LA Club Patron (uncredited)

Neil Durr as Class Reunion Guest (uncredited)

Steffie Grote as Reunion Classmate (uncredited)

Sadarias Harrell as Reunion Classmate (uncredited)

Ryan Hebert as Classmate (uncredited)