John Cusack as Hoops McCann

Demi Moore as Cassandra

Curtis Armstrong as Ack Ack Raymond

William Hickey as Old Man Beckersted

Joe Flaherty as General Raymond

Tom Villard as Clay Stork

Billie Bird as Grandma

John Matuszak as Stain

Mark Metcalf as Aguilla Beckersted

Kimberly Foster as Cookie Cambell

Joel Murray as George Calamari

Matt Mulhern as Teddy Beckersted

Rich Little as Disc Jockey

Bobcat Goldthwait as Egg Stork

Kristen Goelz as Squid Calamari

Donald Li as Chrong Freen

Jeremy Piven as Ty

Bruce Wagner as Uncle Frank

Laura Waterbury as Crossing Guard

Rich Hall as Wilbur

Taylor Negron as Taylor

Linda Warren as Mrs. McCann

Grenville Cuyler as Graduation Orator

Sky as Boscoe

Jennifer Yahoodik as Andrea

Rachel C. Telegen as Brunhelda

Paul M. Lane as Biker #1

Don Ruffin as Biker #2

Gary Littlejohn as Biker #3

Pat McGoarty as Biker #4

Anthony Viveiros as Man on Ferry Boat

Isidore Mankofsky as Cameraman

Al Mohrmann as Yuppie Preacher

Sharon Hope as Aguilla's Maid

Donna Clements as Aguilla's Maid

Alberta Glover as Aguilla's Maid

Pamela Shaddock as Aguilla's Maid

Jerry Winsett as Big Man on Beach

Bill Hoversten as Medic #1

Donald Watson as Medic #2

Lisa Melilli as Ty's Girlfriend

Deborah Bial as Screaming Girl

Bob Gage as Dew Drop Inn Musician

Bob Duncan as Dew Drop Inn Musician

Herb Mingace as Dew Drop Inn Musician

Earl Blank as Dew Drop Inn Musician

Barry Doe as Giant

Scott Richards as Victim

Elizabeth Field as Beautiful Girl

Len Lawrence as Producer

Barry Karas as Doctor

John Blood as Patient

Joan Drott as Nurse

Jim Cooke as Regatta Judge

Robert Boardman as Man Overboard

John Fiore as Crewman