Al Franken as Stuart Smalley

Laura San Giacomo as Julia

Vincent D'Onofrio as Donnie

Shirley Knight as Mom

Harris Yulin as Dad

Lesley Boone as Jodie

John Link Graney as Kyle

Marjorie Lovett as Aunt Paula

Walter Robles as Smalley Uncle

Erik Cord as Smalley Uncle

Denver Mattson as Smalley Uncle

Grant Hoover as Young Stuart

Cory Milano as Young Donnie

Michelle Horn as Young Jodie

Harris Laskawy as Mr. Dimmit

Tom Dugan as Ajax Spokesman

Camille Saviola as Roz Weinstock

Bess Meyer as Laurie

Julia Sweeney as Mea C.

Patrick Kerr as Makeover Artist

Aaron Lustig as Fred

Fred Applegate as Carl

Darrell Larson as Jerry

Dakin Matthews as Intervention Counselor

Jeffrey Joseph as Lawyer

Marte Boyle Slout as Madelyn Doyle

Joe Flaherty as Cousin Ray

Robin Duke as Cousin Denise

Lewis Arquette as Cemetery Official

Mike Hagerty as Cop

PJ Torokvei as Minister

Allen Garfield as Maitre D'

Pamela Brull as Female Diner

Walter Olkewicz as Larry Skoag

Jeremy Roberts as Brad Skoag

Steven Kampmann as Stan Brunner

Robert Curtis Brown as Andy

Violet Ramis as P.A.

Aloma Wright as Autograph Seeker

Rachel Miller as Woman with Subpoena

Kurt Fuller as Von Arks

Walter S. Beaver as Orville Egeberg

Michael C. McCarthy as Merl Egeberg

David Pasquesi as Tollefson

Richard Riehle as Judge

Michael Haley as Bailiff

Ted Raimi as Hal

Rogan Wilde as Ted

Gerrit Graham as Male Diner (uncredited)

Phil Hartman as Announcer (voice) (uncredited)

Kevin Michael Richardson as Man (uncredited)

Justin Roberts as Neighbor (uncredited)

Ken Tipton as Neighbor (uncredited)