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

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

Joey Slotnick

Retirement Home Administrator

Amy Stiller

Rich's Friend's Mom

Stuart Cornfeld

Greeland Air Passenger

Makka Kleist

Bartender

Þórhallur Sigurðsson

Trawler Captain

Martin Lagos

Chilean Sailor

Kai Lennox

Phil Melhoff

Conan O'Brien

Conan O'Brien

Andy Richter

Andy Richter

Lhakpa Sonam Sherpa

Soccer Playing Sherpa

Walter Mudu

TSA Skeleton #1

Liz Mikel

TSA Skeleton #2

Brian Scott McFadden

TSA Officer #1

Dion Graham

TSA Officer #2

Richard DeDomenico

Piano Wholesaler

Matt Levin

Board Meeting Guy

Craig 'Radio Man' Castaldo

News Stand Guy

George Aloi

Life Magazine Employee (uncredited)

Jerome Brooks Jr.

Business Man (uncredited)

Brady Bryson

Boy in Park (uncredited)

Greg Cipes

Time Life Employee (uncredited)

Marmee Regine Cosico

NYC Pedestrian (uncredited)

Samantha Gelnaw

Pedestrian (uncredited)

Rosemary Howard

1940s Winter Pedestrian (uncredited)

Alex Kruz

Time Life Employee (uncredited)

Anna Kuchma

Business Pedestrian (uncredited)

Raymond Mamrak

Office Worker (uncredited)

Jennifer Leigh Mann

Time Life Editor (uncredited)

Ryan McBride

Movie Poster Boy (uncredited)

Ryan Nicolls

Pedestrian (uncredited)

Lil Rhee

New Yorker (uncredited)

Shade Rupe

Pedestrian (uncredited)

Tara Strong

Airport Passenger (uncredited)

Hynden Walch

Time Life Employee (uncredited)

Kelsey Wang

Time Life Employee (uncredited)

Nicole Neuman

Rachel (uncredited)