Owen Wilson as Jack Ryan

Morgan Freeman as Walter Crewes

Gary Sinise as Ray Ritchie

Sara Foster as Nancy Hayes

Willie Nelson as Joe Lurie

Vinnie Jones as Lou Harris

Bebe Neuwirth as Alison Ritchie

Charlie Sheen as Bob Rogers, Jr.

Harry Dean Stanton as Bob Rogers, Sr.

Andrew Wilson as Officer Ned Coleman

Gregory Sporleder as Frank Pizzarro

Brian Keaulana as Barry Salu

Anahit Minasyan as Number 9 (Virginia)

Butch Helemano as Hawaiian Priest

Terry Ahue as Worker #1 (Jimmy Opono)

Pete Johnson as Worker #2 (Con Nuuiwa)

Mike Renfro as Worker #3

Anthony Dorsett as Worker #4

Wendy Thorlakson as Wendy the Party Planner

Beate Antares as Waitress Celia / PBN Girl

John John Florence as John John Florence

Lita Weidenbach as Lady with Shotgun

Leigh French as Lady with Shotgun

Kala Alexander as Kala Alexander

Kelly Slater as Kelly Slater

Steve Jones as Dick, Coleman's Lover