Matthew McConaughey
Ben 'Finn' Finnegan
Kate Hudson
Tess Finnegan
Donald Sutherland
Nigel Honeycutt
Alexis Dziena
Gemma Honeycutt
Ewen Bremner
Alfonz
Ray Winstone
Moe Fitch
Kevin Hart
Bigg Bunny
Malcolm-Jamal Warner
Cordell
Brian Hooks
Curtis
David Roberts
Cyrus
Michael Mulheren
Eddie
Adam LeFevre
Gary
Rohan Nichol
Stefan
Roger Sciberras
Andras
Elizabeth Connolly
Precious Gem Crew Nurse
Harli Ames
Precious Gem Crew Member 1
Tom O'Sullivan
Precious Gem Crew Member 2
Edwina Ritchard
Precious Gen Crew Woman
Duncan Young
Jim
Luke Pegler
Young
Xavier Fernández
Petruchio
Ra Mel El
Moe's Diver
Nicholas Cooper
Moe's Diver
Andrew Allen
Moe's Diver
Glenn Suter
Moe's Diver
Peter Whitford
Judge
Laurence Coy
Finn's Attorney
Linda Cropper
Tess' Attorney
Clementine Heath
Co-Ed Girl 1
Ashley Cheadle
Co-Ed Girl 2
Jason Dundas
Frat Boy 1
Todd Lasance
Frat Boy 2
Ray Bull
Vicar
Valentino del Toro
Barman - Key West
Frank Turner
Old Man 1
Bill Watson
Old Man 2
Henry Browne
Bartender - Topsail Cay
Hannah Hutchins
Hannah (uncredited)