Stiller plays the title role and also served as the director of this latest adaptation of James Thurber's 1939 classic short story, which has left a resounding impact on pop culture over the decades -- although Stiller has said his film is more of a remake of the 1947 version starring Danny Kaye than the actual story itself.
According to the Merriam-Webster dictionary, a "Walter Mitty" is "a commonplace unadventurous person who seeks escape from reality through daydreaming," which certainly sums up Stiller's character.
The 48-year-old actor plays a Mitty for the modern age -- a mid-level employee at a fictionalized version of Life magazine who can't catch a break in his personal or professional life. He has a crush on one of his colleagues, Cheryl (Kristen Wiig
), but can only seem to connect with her in his surreal fantasies. Mitty's mother (Shirley MacLaine
) also grows concerned over her son's wild imagination.
But that all changes when a new manager ("Parks and Recreation" star Adam Scott) wreaks havoc in the office, forcing Mitty to go on a search around the world for a famous photographer, played in a cameo appearance by Sean Penn.
A significant portion of the film examines today's digital age, with more and more print publications like Life struggling to keep up with the times (the real-life Life
ceased printing new issues in 2007 and now exists only in online form).
Stiller says it was important for him to explore this topic.
"It hits home for me," Stiller said, "Because I am of the generation that remembers the 'analog world.'"
"I grew up in the 70s. I remember reel-to-reel tape recorders and Super 8 cameras and just real magazines. It's all going away. So this anaglog-to-digital transition that we're in I think is sort of sad."
Unlike most big-budget Hollywood productions as of late, Stiller shot "Walter Mitty" entirely on traditional celluloid.
"Everything that everyone does now with digital cinematography is about trying to replicate the look of film," he said. "Why do we need to replicate it when we can just still shoot on film?…I'll always be a film guy."
Watch video above to see Stiller talk more about his latest project, and to hear Wiig
describe what it was like shooting her first-ever full-fledged action sequence.