Chris Messina as Ira Black

Jennifer Westfeldt as Abby Willoughby

David Margulies as Dr. Arnold Friedman

Kali Rocha as Tracy

Kevin Sussman as Lenny

Marylouise Burke as Janice

Judith Light as Arlene Black

Robert Klein as Seymour Black

Fred Willard as Michael Willoughby

Frances Conroy as Lynne Willoughby

Malachy McCourt as First Justice of the Peace

Modi as Marvin the Limo Driver

Ramón Rodríguez as Julio the Subway Mugger

Jason Alexander as Dr. Morris Saperstein

Chris Parnell as Dr. Ronald Silverberg

Jon Hamm as Ronnie

Darrell Hammond as Dr. Lawrence Rosenblum

BD Wong as Party Guest

Spiro Malas as Greek Waiter

Brad Bellamy as Henry

Michael McGrath as Tony the Doorman

Toni Di Buono as Woman Mugged on Subway

Ed Blank as Harry Goldfarb

Jennifer Albano as Movie Theater Cashier

Maddie Corman as Lea

Matthew Del Negro as Seth

Ken Barnett as Bobby, Jingle Singer # 1

Gregory Jbara as Jingle Singer # 2

Robert Bagnell as Jimmy the Sound Guy

Joe Buck as Himself

Robert Levine as Second Justice of the Peace

Asa Somers as Gus

Ilana Levine as Dr. Aurora Finkelstein

Amy Wilson as Female Patient

Hayden Adams as Man Mounted on Subway

Donna Murphy as Dr. Betsy Goldman