Melinda and Melinda
While dining out with friends, Sy suggests the difficulty of separating comedy from tragedy. To illustrate his point, he tells his guests two parallel stories about Melinda ; both versions have the same basic elements, but one take on her state of affairs leans toward levity, while the other is full of anguish. Each story involves Melinda coping with a recent divorce through substance abuse while beginning a romantic relationship with a close friend's husband.
Chiwetel Ejiofor
Ellis Moonsong
Will Ferrell
Hobie
Jonny Lee Miller
Lee
Radha Mitchell
Melinda Robicheaux
Amanda Peet
Susan
Chloë Sevigny
Laurel
Wallace Shawn
Sy
David Aaron Baker
Steve
Arija Bareikis
Sally Oliver
Josh Brolin
Greg
Steve Carell
Walt
Stephanie Roth Haberle
Louise
Shalom Harlow
Joan
Geoffrey Nauffts
Bud
Zak Orth
Peter
Larry Pine
Max
Vinessa Shaw
Stacey
Brooke Smith
Cassie
Daniel Sunjata
Billy
Matt Servitto
Jack Oliver
Andy Borowitz
Doug
Neil Pepe
Al
Michael J. Farina
Man With Dog
Christina Kirk
Jennifer
Alyssa Pridham
Acting Student
Katie Kreisler
Director
Quincy Rose
2nd A.D.
Rick Holmes
Party Guest
Michelle Durning
Party Guest
Rob Buntzen
Antique Shop Owner
Daniel Sunjata
Billy Wheeler
Vinessa Shaw
Stacey Fox
Lauren Adler
Waitress (uncredited)