Stuart Smalley

Al Franken

Julia

Laura San Giacomo

Donnie

Vincent D'Onofrio

Mom - The Smalley Family

Shirley Knight

Dad - The Smalley Family

Harris Yulin

Jodie

Lesley Boone

Kyle - The Smalley Family

John Link Graney

Aunt Paula

Marjorie Lovett

Mea C. - Chicago Public Access

Julia Sweeney

Smalley Uncle

Walter Robles

Announcer (voice) (uncredited)

Phil Hartman

Smalley Uncle

Erik Cord

Smalley Uncle

Walt Robles

Smalley Uncle

Denver Mattson

Young Stuart

Grant Hoover

Young Donnie

Cory Milano

Young Jodie

Michelle Horn

Mr. Dimmit

Harris Laskawy

Ajax Spokesperson

Tom Dugan

Roz Weinstock

Camille Saviola

Judge

Richard Riehle

Laurie

Bess Meyer

Hal

Ted Raimi

Makeover Artist

Patrick Kerr

Fred

Aaron Lustig

Carl

Fred Applegate

Jerry

Darrell Larson

Intervention Counselor

Dakin Matthews

Lawyer

Jeffrey Joseph

Madelyn Doyle

Marte Boyle Slout

Cousin Ray

Joe Flaherty

Cousin Denise

Robin Duke

Cemetery Official

Lewis Arquette

Cop

Michael G. Hagerty

Minister

PJ Torokvei

Maitre d'

Allen Garfield

Female Diner

Pamela Brull

Larry Skoag

Walter Olkewicz

Brad Skoag

Jeremy Roberts

Stan Brunner

Steven Kampmann

Andy

Robert Curtis Brown

Production Assistant

Violet Ramis

Autograph Seeker

Aloma Wright

Woman with Subpoena

Rachel Miller

Von Arks

Kurt Fuller

Orville Egeberg

Walter S. Beaver

Merl Egeberg

Michael C. McCarthy

Tollefson

David Pasquesi

Bailiff

R.M. Haley

Bailiff

Michael Haley

Ted

Rogan Wilde

Male Diner (uncredited)

Gerrit Graham

Harris Laskaway

Man (uncredited)

Kevin Michael Richardson

Neighbor (uncredited)

Justin Roberts

Neighbor (uncredited)

Ken Tipton