After a number of different production complications, producers of The Secret Life of Walter Mitty settled on the accomplished director of comedies, Ben Stiller, to both direct and star in the remake of James Thurber's classic story. Having previously directed a number of broad comedies such as Zoolander and Tropic Thunder, Stiller had an opportunity with The Secret Life of Walter Mitty to return to more tonally nuanced material, for the first time since his breakout hit Reality Bites.
In an interview about his process directing the film, Stiller told Variety, “I love acting, but what I love is the freedom you have as a director to tell all different kinds of stories, where as an actor, to a certain extent you’re just limited to who you are and what you get cast in. The process is less vulnerable when you’re directing, because you’re supposedly in control.”
Stiller was drawn to the material of Mitty in part because of the opportunity it presented to tackle more adult themes. In spite of his proficiency as a film director, he still had to convince producers that he was the right man for the job, producing a five-minute short reel as evidence of his ideas for style and tone. Of his interest in the film, Stiller told NPR, "I definitely related to the moments in life where you try to be your best possible self, but you can't quite pull it off. Or you just aren't, in the moment, who you want to be. Or you think of that thing to say to somebody, the comeback for somebody, when you think of it 10 minutes later and they're gone."