Ben Stiller

Walter Mitty

Kristen Wiig

Cheryl Melhoff

Sean Penn

Sean O'Connell

Shirley MacLaine

Edna Mitty

Adam Scott

Ted Hendricks

Kathryn Hahn

Odessa Mitty

Patton Oswalt

Todd Maher

Adrian Martinez

Hernando

Ólafur Darri Ólafsson

Helicopter Pilot

Gunnar Helgason

Hotel Keeper

Terence Bernie Hines

Gary Mannheim

Alex Anfanger

Ted's Toner Box Associate

Gary Wilmes

Walter's Dad

Jon Daly

Tim Naughton

Gurdeep Singh

Cab Driver

Paul Fitzgerald

Don Proctor

Grace Rex

Cheryl's Co-Worker

Amanda Naughton

Female Editor

Joey Slotnick

Retirement Home Administrator

Amy Stiller

Rich's Friend's Mom

Ari Matthíasson

Trawler 1st Mate

José Alcántara

Chilean Sailor

Kai Lennox

Phil Melhoff

Conan O'Brien

Conan O'Brien

Andy Richter

Andy Richter

Anthony Desio

Mover

Lhakpa Sonam Sherpa

Soccer Playing Sherpa

Walter Mudu

TSA Skeleton #1

Liz Mikel

TSA Skeleton #2

Dion Graham

TSA Officer #2

Richard DeDomenico

Piano Wholesaler

Matt Levin

Board Meeting Guy

Craig 'Radioman' Castaldo

News Stand Guy

George Aloi

Life Magazine Employee (uncredited)

Greg Cipes

Time Life Employee (uncredited)

Gary Ferster

Time Life Employee (uncredited)

Rosemary Howard

1940s Winter Pedestrian (uncredited)

Alex Kruz

Time Life Employee (uncredited)

Anna Kuchma

Business Pedestrian (uncredited)

Raymond Mamrak

Office Worker (uncredited)

Shade Rupe

Pedestrian (uncredited)

Joshua Schubart

Mover (uncredited)

Tara Strong

Airport Passenger (uncredited)

Barbara Vincent

Businesswoman (uncredited)

Hynden Walch

Time Life Employee (uncredited)

Kelsey Wang

Time Life Employee (uncredited)