Keegan-Michael Key

Jack

Kate Micucci

Allison

Gillian Jacobs

Samantha

Pete Holmes

Self

Sondra James

Bonnie

Richard Masur

Lou

Richard Kline

Mr. Coughlin

Seth Barrish

Timothy

Miranda Bailey

Producer

Erin Darke

Natasha

Mike Birbiglia

Miles

Brandon Scott Jones

Audience Chuck

Emily Skeggs

Shy Sarah

Sunita Mani

Amy

Gary Richardson

Gary

Chris Gethard

Bill

Tami Sagher

Lindsay

Glenn Wein

Psychiatrist

Neil Fleischer

Pianist Seth

Steve Waltien

Hugh Finn

Kati Rediger

Alicia Bonham

Hallie Bulleit

Audience Claudia

Garth Kravits

Doctor

Jason C. Brown

Studio Page

Andy Bohn

Executive Producer