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
as Ellis Moonsong
Will Ferrell
as Hobie
Jonny Lee Miller
as Lee
Radha Mitchell
as Melinda Robicheaux
Amanda Peet
as Susan
Chloë Sevigny
as Laurel
Wallace Shawn
as Sy
David Aaron Baker
as Steve
Arija Bareikis
as Sally Oliver
Josh Brolin
as Greg
Steve Carell
as Walt
Stephanie Roth Haberle
as Louise
