Edward Burns

Paulie

John Leguizamo

TC (Tony)

Matthew Lillard

Desmond 'Dez' Howard

Donal Logue

Jimbo

Jay Mohr

Cousin Mike Sullivan

Brittany Murphy

Sue

Heather Burns

Jules

Shari Albert

Tina Howard

Jessica Capshaw

Jen

John F. O'Donohue

Pops

Spencer Fox

Little Jack

Amy Leonard

Crystal

Arthur J. Nascarella

Mr. B

Joe Pistone

Top Cat

John Russo-Zirkel

Little Matt

Jamie Tirelli

TC's Dad

Kevin Kash

Strip Club MC

Tito Ruiz

Man in Bar

Marion McCorry

Paulie's Mom (uncredited)

John Mahoney

Paulie's Dad (uncredited)

Catharine Bolz

Dez's Mom (uncredited)

Isaac Gabaeff

Butter Tongue Roadie (uncredited)

Claudia L. Brown

Pole Dancer (uncredited)

Julie McNiven

Girl with Band (uncredited)