Don't Think Twice

Keegan-Michael Key

Jack

Gillian Jacobs

Samantha

Chris Gethard

Bill

Kate Micucci

Allison

Tami Sagher

Lindsay

Mike Birbiglia

Miles

Richard Masur

Lou

Sondra James

Bonnie

Richard Kline

Mr. Coughlin

Emily Skeggs

Shy Sarah

Brandon Scott Jones

Audience Chuck

Sunita Mani

Amy

Glenn Wein

Psychiatrist

Neil Fleischer

Pianist Seth

Erin Darke

Natasha

Gary Richardson

Gary

Steve Waltien

Hugh Finn

Kati Rediger

Alicia Bonham

Hallie Bulleit

Audience Claudia

Garth Kravits

Doctor

Jason C. Brown

Studio Page

Pete Holmes

Self

Seth Barrish

Timothy

Miranda Bailey

Producer

Adam Pally

Robbie

Matthew Star

Improv Student

Josh Rabinowitz

Josh

Maggie Kemper

Liz

Lena Dunham

Self

Ben Elkins

ELEL

Jo-Jo Jackson

ELEL

Tim Cook

ELEL

Zach Tichenor

ELEL

Steve Frederick

ELEL

Frderick Weathersby

ELEL

Alex Mojaverian

ELEL

Gavin Speiller

Autograph Speaker

Ben Stiller

Self

Jordan Kenneth Kamp

Audience Jim

Colby Minifie

Audience Neil

Rachel Pegram

Audience Sarah

Tim Martin

Audience Tony

Robert King

Heckler

Kevin Barnett

Writer Terry

Brian Edwards

Bouncer

Jo Firestone

Jo

Connor Ratliff

Connor

Elise Edwards

Improv Intern (uncredited)

DeWitt Fleming Jr.

Subway Bucket Drummer (uncredited)

Ira Glass

Man on TV (uncredited)

Annamaria Sofillas

Audience Member (uncredited)

Sean Toney

Audience Member (uncredited)

Jo Yang

Sewing Lady (uncredited)