Evan Rachel Wood
Melodie St. Ann Celestine

Michael McKean
Joe - Boris' Friend #3

Conleth Hill
Leo Brockman

Patricia Clarkson
Marietta

Ed Begley Jr.
John

Carolyn McCormick
Jessica

Henry Cavill
Randy James

John Gallagher Jr.
Perry

Christopher Evan Welch
Howard

Lyle Kanouse
Boris' Friend #2

Clifford Lee Dickson
Boy on Street

Yolonda Ross
Boy's Mother

Samantha Bee
Chess Mother

Marcia DeBonis
Lady at Chinese Restaurant

Willa Cuthrell-Tuttleman
Chess Girl

Nicole Patrick
Perry's Friend

Olek Krupa
Morgenstern

Jessica Hecht
Helena

Lindsay Michelle Nader
Television Voice (voice)

Armand Schultz
Television Voice (voice)