Ben Stiller has lived many lives in Hollywood. He was an Emmy-winning writer before turning 30, thanks to his short-lived variety series The Ben Stiller Show . By 40, he was toplining comedy box-office smashes, including Meet the Parents and Zoolander. Then he turned toward prestige, from an Emmy-nominated turn poking brutal fun at himself in Ricky Gervais ’s Extras to a Spirit Award nomination for his acerbic work in Noah Baumbach ’s Greenberg. All along, Stiller was directing too—breaking out with the Gen-X classic Reality Bites before making movies as varied as industry satire Tropic Thunder and earnest fantastical drama The Secret Life of Walter Mitty . A guide to Hollywood’s biggest races Arrow

In 2025, as Stiller openly discusses on this week’s Little Go

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