Al Franken

Stuart Smalley

Laura San Giacomo

Julia

Vincent D'Onofrio

Donnie

Shirley Knight

Mom

Harris Yulin

Dad

Lesley Boone

Jodie

John Link Graney

Kyle

Marjorie Lovett

Aunt Paula

Walter Robles

Smalley Uncle

Erik Cord

Smalley Uncle

Denver Mattson

Smalley Uncle

Grant Hoover

Young Stuart

Cory Milano

Young Donnie

Michelle Horn

Young Jodie

Harris Laskawy

Mr. Dimmit

Tom Dugan

Ajax Spokesman

Camille Saviola

Roz Weinstock

Bess Meyer

Laurie

Julia Sweeney

Mea C.

Patrick Kerr

Makeover Artist

Aaron Lustig

Fred

Fred Applegate

Carl

Darrell Larson

Jerry

Dakin Matthews

Intervention Counselor

Jeffrey Joseph

Lawyer

Marte Boyle Slout

Madelyn Doyle

Joe Flaherty

Cousin Ray

Robin Duke

Cousin Denise

Lewis Arquette

Cemetery Official

Mike Hagerty

Cop

PJ Torokvei

Minister

Allen Garfield

Maitre D'

Pamela Brull

Female Diner

Walter Olkewicz

Larry Skoag

Jeremy Roberts

Brad Skoag

Steven Kampmann

Stan Brunner

Robert Curtis Brown

Andy

Violet Ramis

P.A.

Aloma Wright

Autograph Seeker

Rachel Miller

Woman with Subpoena

Kurt Fuller

Von Arks

Walter S. Beaver

Orville Egeberg

Michael C. McCarthy

Merl Egeberg

David Pasquesi

Tollefson

Richard Riehle

Judge

Michael Haley

Bailiff

Ted Raimi

Hal

Rogan Wilde

Ted

Gerrit Graham

Male Diner (uncredited)

Phil Hartman

Announcer (voice) (uncredited)

Kevin Michael Richardson

Man (uncredited)

Justin Roberts

Neighbor (uncredited)

Ken Tipton

Neighbor (uncredited)