Michael Showalter as Elliot Sherman

Elizabeth Banks as Caroline Swann

Michelle Williams as Cecil Mills

Justin Theroux as Bradley Lake

Zak Orth as Wendall Wimms

Michael Ian Black as Ed

Catherine Lloyd Burns as Stella

Peter Dinklage as Benson Hedges

Paul Rudd as Dan Abbott

Katharine Powell as Sonya Simmons

Jon DeVries as Alan Swann

Donna Mitchell as Judy Swann

Haviland Morris as Kate Lewis

David Wain as Louis Lewis

Jim DeMarse as Leonard Sherman

Leslie Lyles as Sheila Sherman

A.D. Miles as Bar Baxter #1

Joe Lo Truglio as Bar Baxter #2

Seth Herzog as Bar Baxter #3

Jonathan Marc Sherman as Deaf Bar Baxter

Peter Stadlen as Young Elliot

Abby Wathen as Kimberly

Gabriel Millman as Max

Sarah Drew as Serena

Chris Spain as Tanner Bates

Marylouise Burke as Delores

Ken Marino as Jack Mechanic

Audrie Neenan as Pastor Pritchard

Bobby Tisdale as Emcee

Michael Portnoy as Interpretive Dancer

Maya Goldsmith as Muffy

Jenny Maguire as Peg

Jack McBrayer as Elliot's Friend