Vince Vaughn as Ronny Valentine

Kevin James as Nick Brannen

Winona Ryder as Geneva Brannen

Jennifer Connelly as Beth

Queen Latifah as Dana

Channing Tatum as Zip

Clint Howard as Herbert Trimpy

Rance Howard as Burt

Laura Whyte as Sue

Amy Morton as Diane Popovich

Talulah Riley as Concept Car Spokesmodel

Chelcie Ross as Thomas Fern

Heidi Johanningmeier as Shoot the Puck Girl

Rebecca Spence as Jackie

Grace Rex as Cousin Betty

Mimi Sagadin as B & V Worker

Eduardo N. Martinez as Felix

Guy Van Swearingen as Saul

Troy West as Dr. Rosenstone

Mike McNamara as Cousin James

Tim Rhoze as Charles

Madison Dirks as B & V Worker

Michael Patrick Thornton as B & V Worker

Sandy Marshall as Medic at Gardens

William Smillie as Poissonier

Jillian Burfete as Restaurant Server

Katie Korby as Restaurant Server

Catherine Bruzzini as Restaurant Patron

Laura Cooper as Waitress

Mariko Hayashi-Hall as Vietnamese Parlor Owner

Cheryl Hamada as Vietnamese Parlor Worker

Gary Houston as Camera Clerk

Wendy George as Store Clerk

Keith Kupferer as Bank Customer

Kevin Bigley as Bank Customer

Christina Anthony as Bank Customer

Philip Rayburn Smith as Gilbert

Elaine Robinson as Mom

Noah Jerome Schwartz as Son

Chanté René Linwood as El Train Patron

Kielor Roberts as Diane's Son

Benjamin Toby Mullinkosson as Skate Rat

Nick Brade as Skate Rat

Michael Trnka as Skate Rat

Karen Aldridge as Receptionist

Gene Honda as Shoot the Puck Announcer

Brennan Buhl as Shoot the Puck Guy

William M. Connor as Disgruntled Fan

Christopher Meister as Concession Stand Customer

Charlie Hilbrant as Concession Stand Customer

DuShon Monique Brown as Weiner Circle Worker (uncredited)

Duke Czlonka as Restaurant Patron (uncredited)

Joe DeBartolo as Blackhawks Fan (uncredited)

Shannon Edwards as Palm Garden Docent (uncredited)

Jessica Starr Folger as Blackhawks Fan (uncredited)

Andrew Lee as Gambler (uncredited)

Matthew LeFevour as Ice Security (uncredited)

Ashley Lobo as Blackhawks Ice Crew Girl (uncredited)

Bernadette Lords as Jeep Auto Representative (uncredited)

Dave McNulty as Businessman in Lobby (uncredited)

Carmine Perrelli as Bar Patron (uncredited)

Eric Pierson as Bank Customer (uncredited)

Steven James Price as Chrysler Executive (uncredited)

Aaron Sauerland as Blackhawks Fan (uncredited)

Walt Sloan as Chrysler Employee (uncredited)

Jason Stebbings as El Train Rider (uncredited)

January Stern as Chrysler Executive (uncredited)

Stephanie Swearingen as Auto Show Attendee (uncredited)