Emily & Tim

Olympia Dukakis

Emily (Segment 6)

Louis Zorich

Tim (Segment 6)

Adam Rose

Posnick (Segment 1)

Luke Brandon Field

Lerner (Segment 1)

Thomas Mann

Tim (Segment 1)

Zosia Mamet

Emily (Segment 1)

Jeremy Jordan

Phayer (Segment 1)

Alexis Bledel

Emily (Segment 2)

Cara Buono

Emily (Segment 3)

Kal Penn

Tim (Segment 2)

Andre Braugher

Tim (Segment 5)

Phylicia Rashād

Emily (Segment 5)

Kathleen Turner

Narrator

Drena De Niro

Sheilda Posnick (Segment 4)

Dana Eskelson

Sarah (Segment 4)

Dre Davis

Jo Ann (Segment 1)

Dominic Fumusa

Tim (Segment 3)

Adepero Oduye

Meg (Segment 5)

Jennifer Damiano

Helayne Specter

Alexis Molnar

Meg Hanratty (segment 'Betrayal')