Jeremy Piven as Don Ready

Ving Rhames as Jibby Newsome

James Brolin as Ben Selleck

David Koechner as Brent Gage

Kathryn Hahn as Babs Merrick

Ed Helms as Paxton Harding

Jordana Spiro as Ivy Selleck

Tony Hale as Wade Zooha

Ken Jeong as Teddy Dang

Rob Riggle as Peter Selleck

Alan Thicke as Stu Harding

Charles Napier as Dick Lewiston

Jonathan Sadowski as Blake

Noureen DeWulf as Heather

Wendie Malick as Tammy Selleck

Craig Robinson as DJ Request

Bryan Callen as Jason

Joey Kern as Ricky

Kristen Schaal as Stewardess Stacey

Chris Gartin as Selleck Customer - Husband

Jessica St. Clair as Selleck Customer - Wife

Mary Castro as Stripper

Gary Sanchez as Passenger Mariachi

Matt Walsh as Captain Ortiz

Samantha Albert as Selleck Auto Trader Customer

Ian Roberts as Selleck Customer - Gary

Jean Villepique as Selleck Customer - Mother

Brooke Lenzi as Karaoke Pretty Girl

Morgan Murphy as Karaoke Bartender

Gwen Stewart as McDermott Angel

Courtney Alain Bradshaw as McDermott Angel

T.J. Miller as Cessna Jim

Molly Erdman as Selleck Customer of Zooha

Paul Lieberstein as Selleck Last Customer

Erica Vittina Phillips as Selleck Customer - Teddy

Sabrina Renata Maahs as Don's Stripper

Brianne Van Cuyck as Brent's Stripper

Will Ferrell as McDermott (uncredited)

Gina Gershon as (uncredited)

Bradley Steven Perry as Young Don Ready (uncredited)

Nancy Young as Customer / Rioter (uncredited)

Cheryl Lyone as Excited Customer (uncredited)