Unbeatable Harold

Gordon Michaels

Harold

Nicole DeHuff

Wanda Livingston

Dylan McDermott

Jake Salamander

Henry Winkler

Fullerton

Gladys Knight

Phyllis

Taryn Manning

Sandy

Phyllis Diller

Mrs. Clancy

Lin Shaye

Jeannie

Charles Durning

Harold's Father

Tim Russ

Diner Manager

Michelle Phillips

Erma

Annabella Gutman

Groupie #1

Amy Weber

Cocktail Waitress

Lourdes Benedicto

Cinnamon

Mark Engelhardt

The Loser

Joleigh Fioravanti

Bar Girl #1

Pat Germano

Gas Attendant

Amy Hill

Secretary

Fiona Horne

Cherry

Michael John Hurley

Drive-thru Guy

Erin Keegan

Harold's Mom

Mike N. Kelly

Donnie James

Jennifer Kincer

Gail Harstead - Newscaster

Bill Kirchenbauer

Short Order Cook

Conchita Leeflang

Ursula

Willam Belli

Anita Boner

Michael B. Silver

Father

Herb Santos Jr.

Sports Book Guy