Lewis Black as Oliver Porter

Wilmer Valderrama as Zach Van Bourke

Tyler James Williams as Charlie Goldfinch

Dyllan Christopher as Spencer Davenport

Brett Kelly as Timothy 'Beef' Wellington

Gia Mantegna as Grace Conrad

Quinn Shephard as Donna Malone

Paget Brewster as Valerie Davenport

Rob Corddry as Sam Davenport

Dominique Saldaña as Katherine Davenport

Jessica Walter as Cindi

Rob Riggle as Head Guard Hoffman

Michelle Sandler as Mary Lynn

David Koechner as Ernie

B.J. Novak as Desk Attendant

Mindy Kaling as Restaurant Hostess

Kevin McDonald as Guard in the Hall #1

Bruce McCulloch as Guard in the Hall #2

Mark McKinney as Guard in the Hall #3

Dave Allen as Gas Station Attendant

Steve Bannos as Tree Salesman

Tony Hale as Alan Davies

Cedric Yarbrough as Melvin Goldfinch

Kristen Wiig as Carole Malone

Nick Thune as Handsome Santa

Heather Beers as Flight Attendant

Allie Mac Kay as Perky Presenter

Sandra Tsing Loh as UM Room Attendant

Michael Maiello as UM Room Attendant

Wayne Federman as Airport Attendant

Annette Wright as Airport Attendant

Ben Falcone as Santa at Mall

Al Roker as Self

Stan Ellsworth as Huge Guy at Hotel

Stephen Liska as Hotel Desk Clerk

Lauren McKnight as Jetsetter

Noah Bastian as Jetsetter

Shareece Pfeiffer as Pretty Mall Girl

Darren Ewing as Admiral's Club Host

Joe Lookinland as Bully

Brooks Bedore as Bully

Lerin Porter as Owen Marks

Gary Morgan as Baggage Handler

Jim Wilkey as Baggage Handler

Hayden Holbrook as Bathroom Boy

Benjamin Ho as Bathroom Boy

Tyler Scott Drewes as Tough Kid

Kim W. Powell as Ivy League Santa

Micaela Nelligan as Beef's Mom

Conrad E. Palmisano as Santa

Haley Fife as Beef's Pretty Girl

Alisa Taylor as Girlfriend

Ana Queren Seabra as Girlfriend

Mallory Bouchard as Girlfriend

Thomas Conroy as Security Monitor

Cal Nguyen as Soldier (uncredited)

Teri Garr as Aunt Judy / Valerie’s Sister