Larry David as Boris Yellnikoff

Evan Rachel Wood as Melodie St. Ann Celestine

Michael McKean as Joe - Boris' Friend #3

Conleth Hill as Leo Brockman

Patricia Clarkson as Marietta

Ed Begley Jr. as John

Carolyn McCormick as Jessica

Henry Cavill as Randy James

John Gallagher Jr. as Perry

Christopher Evan Welch as Howard

Adam Brooks as Boris' Friend #1

Lyle Kanouse as Boris' Friend #2

Clifford Lee Dickson as Boy on Street

Yolonda Ross as Boy's Mother

Samantha Bee as Chess Mother

Marcia DeBonis as Lady at Chinese Restaurant

Willa Cuthrell-Tuttleman as Chess Girl

Nicole Patrick as Perry's Friend

Olek Krupa as Morgenstern

Jessica Hecht as Helena

Lindsay Michelle Nader as Television Voice (voice)

Armand Schultz as Television Voice (voice)

Kristen Ruhlin as Melodie Club Friend #3 (uncredited)