Don't Think Twice

Keegan-Michael Key

As Jack

Gillian Jacobs

As Samantha

Chris Gethard

As Bill

Kate Micucci

As Allison

Tami Sagher

As Lindsay

Mike Birbiglia

As Miles

Richard Masur

As Lou

Sondra James

As Bonnie

Richard Kline

As Mr. Coughlin

Emily Skeggs

As Shy Sarah

Brandon Scott Jones

As Audience Chuck

Sunita Mani

As Amy

Glenn Wein

As Psychiatrist

Neil Fleischer

As Pianist Seth

Erin Darke

As Natasha

Gary Richardson

As Gary

Steve Waltien

As Hugh Finn

Kati Rediger

As Alicia Bonham

Hallie Bulleit

As Audience Claudia

Garth Kravits

As Doctor

Jason C. Brown

As Studio Page

Pete Holmes

As Self

Seth Barrish

As Timothy

Miranda Bailey

As Producer

Adam Pally

As Robbie

Matthew Star

As Improv Student

Josh Rabinowitz

As Josh

Maggie Kemper

As Liz

Lena Dunham

As Self

Ben Elkins

As ELEL

Jo-Jo Jackson

As ELEL

Tim Cook

As ELEL

Zach Tichenor

As ELEL

Steve Frederick

As ELEL

Frderick Weathersby

As ELEL

Alex Mojaverian

As ELEL

Gavin Speiller

As Autograph Speaker

Ben Stiller

As Self

Jordan Kenneth Kamp

As Audience Jim

Colby Minifie

As Audience Neil

Rachel Pegram

As Audience Sarah

Tim Martin

As Audience Tony

Robert King

As Heckler

Kevin Barnett

As Writer Terry

Brian Edwards

As Bouncer

Jo Firestone

As Jo

Connor Ratliff

As Connor

Elise Edwards

As Improv Intern (uncredited)

DeWitt Fleming Jr.

As Subway Bucket Drummer (uncredited)

Ira Glass

As Man on TV (uncredited)

Annamaria Sofillas

As Audience Member (uncredited)

Sean Toney

As Audience Member (uncredited)

Jo Yang

As Sewing Lady (uncredited)