Matthew McConaughey as Ben 'Finn' Finnegan

Kate Hudson as Tess Finnegan

Donald Sutherland as Nigel Honeycutt

Alexis Dziena as Gemma Honeycutt

Ewen Bremner as Alfonz

Ray Winstone as Moe Fitch

Kevin Hart as Bigg Bunny

Malcolm-Jamal Warner as Cordell

Brian Hooks as Curtis

David Roberts as Cyrus

Michael Mulheren as Eddie

Adam LeFevre as Gary

Rohan Nichol as Stefan

Roger Sciberras as Andras

Elizabeth Connolly as Precious Gem Crew Nurse

Harli Ames as Precious Gem Crew Member 1

Tom O'Sullivan as Precious Gem Crew Member 2

Edwina Ritchard as Precious Gen Crew Woman

Duncan Young as Jim

Luke Pegler as Young

Xavier Fernández as Petruchio

Ra Mel El as Moe's Diver

Nicholas Cooper as Moe's Diver

Andrew Allen as Moe's Diver

Glenn Suter as Moe's Diver

Peter Whitford as Judge

Laurence Coy as Finn's Attorney

Linda Cropper as Tess' Attorney

Clementine Heath as Co-Ed Girl 1

Ashley Cheadle as Co-Ed Girl 2

Jason Dundas as Frat Boy 1

Todd Lasance as Frat Boy 2

Ray Bull as Vicar

Valentino del Toro as Barman - Key West

Frank Turner as Old Man 1

Bill Watson as Old Man 2

Henry Browne as Bartender - Topsail Cay

Hannah Hutchins as Hannah (uncredited)