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Ben Stiller is best known for his legendary comedy career—with unforgettable performances in Zoolander, Meet the Parents, Tropic Thunder, and There’s Something About Mary. But in recent years, Ben Stiller redefined himself as a powerhouse director and producer—especially with the critically acclaimed Apple TV+ thriller Severance.
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You laughing at me
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Yeah, no, I'm gonna fool you all, but tonight I'll be on headlines all over the world
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That is 21-year-old Ben Stiller in a 1986 Broadway production of The House of Blue Leaves
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He was still a couple of years away from finding fame and fortune in Hollywood, but even then he was effortlessly getting laughs. So it wasn't too surprising that a decade later
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he would become one of the biggest comedic stars in history. What was surprising, however
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was when he decided to sever himself from the world of comedy and become an auteur director
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And if you're wondering how that severance is going, well, we're gonna tell you all about it
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At age 12, I weighed 319 pounds. Now, I eat success for breakfast with skim milk
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Born in 1965, Benjamin Edward Mira Stiller is the second child of legendary showbiz couple
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Jerry Stiller and Anne Mira, who rose to fame in the 1960s as the comedy team Stellar and Mira
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Given who his parents were, young Ben found himself on sets for TV shows at a young age
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He had made his debut as an actor on the legal drama Kate McShane, which not coincidentally starred his mother in the title role
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but the series was canceled before Ben's episode aired. After seeing his first episode of Second City Television in high school
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he decided he wanted to do sketch comedy, and it is as a comedic actor that the world first got to know him
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He appeared in a short film called The Hustler of Money, that aired on an episode of Saturday Night Live in 1987
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In 1988, Stiller created the Ben Stiller Show for MTV. Then in 1992, Stiller broke through in movies
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by starring in the romantic comedy Reality Bites. After that, he was a pretty regular presence on the big screen
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You could trouble me for a warm glass of shut the hell up. Check out the name tag
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You're in my world now, Grandma. Appearing mostly in comedies, like There's Something About Mary
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Meet the Parents Zoolander Starsky and Hutch Dodgeball and the Night at the Museum films And Stiller was everywhere But unless you the kind of person who pays attention to directors you might have missed that Stiller was directing some of these movies as well
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I had no idea you could milk a cat. Oh yeah, you can milk anything with nipples
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I have nipples, Greg. Could you milk me? In fact, even his breakthrough film role in Reality Bites was one he directed himself
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That was quickly followed up by a directing gig on Jim Carrey's 1996 hit
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The Cable Guy. but after that, Stiller exclusively directed vehicles for himself. These include his 2001
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cult hit Zoolander, his 2008 mega hit Tropic Thunder, the 2013 adventure comedy The Secret
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Life of Walter Mitty, and the disappointing 2016 sequel Zoolander 2. Now, given every other film
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he's ever directed has been a box office success, you'd think the failure of that last one would be
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easy to shrug off, but Stiller took it very personally. Did you ever think that maybe there's
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more to life than being really, really, really ridiculously good-looking? The first Zoolander had become a cult classic, and according to Stiller, he only made the second
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one because he thought it was something everyone wanted. So when it was savaged by critics and
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ignored by fans, he blamed himself for the failure, telling himself, I must have really f***ed this up
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You guys look so lame. I love it, dude. You ninjas dressed up all old school just to meet me
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So Jedi. You guys suck. Both of you guys suck. You look great, man
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That, in turn, caused Stiller to begin to doubt his talents and his ability to tell what was funny
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In his own words, Had Zoolander 2 been a success, Stiller assumes he would have jumped into making Zoolander 3
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or some other big studio comedy. But its failure gave him pause to reevaluate his whole life and career
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Who am I? I don't know. I guess I have a lot of things to ponder
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Of course, Zoolander wasn't entirely to blame. At the same time, Stiller's marriage to actress Christine Taylor
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with whom he co in Dodgeball was on The Rocks should mate you okay fine I just threw up at my mouth a little rocks Married in 2000 the couple separated in 2017 Stiller looked inward to
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turn things around, and that started with some decisions about his acting. As he would later
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recall, I kind of made the choice a few years ago that I was only going to do something if it really
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hit me. And he meant it. In fact, not only did Stiller get choosier about his parts, he pretty
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much stopped starring in movies altogether. Sure, he still showed up for the occasional bit part or
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cameo, but between 2017 and 2024, Stiller didn't play the lead in a single feature film, comedy or
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otherwise. Look, no offense, but just, I mean, it's just not a good fit anymore. Instead, Stiller
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decided to lean into directing again, only he wasn't interested in comedies. On the contrary
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shortly after the separation, Stiller dove headfirst into helming the crime drama TV miniseries
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Escape at Dannemora for Showtime. Based on the real-life events surrounding the 2015 Clinton Correctional Facility Escape
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the series received near-universal acclaim from critics and would garner seven Emmy nominations
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It wasn't as surprising as it seemed. Stiller has always considered himself an auteur filmmaker
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who just happened to be pigeonholed into the world of comedy, and his first steps toward creating more dramatic stories
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really started with his work on The Secret Life of Walter Mitty. But Escape at Dannemora was a clear indicator of the new direction
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he was taking with his career. And more importantly, it would directly lay the groundwork
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for the more serious tone he would adopt in his subsequent project, Severance
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After reconciling with Taylor during the pandemic in 2020, Stiller was able to fully focus his attention on Severance
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A sci-fi psychological thriller, Severance follows the life of a man who works at a shady biotech corporation
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The company requires its employees to wear an implant that allows them to erase the employees' memories
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of the outside world when they're at the job, and vice versa a procedure known as severance The first two seasons contain 19 episodes and Stiller directs 11 of them Near the end I was like oh I hope people get it I hope they like it We been working on this thing for a couple of years This could be either good or it could
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just be like, oh. And while we're not going to give anything away, we will say that the
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stylish series quickly became a massive hit celebrated by both critics and audiences and
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is now widely regarded as one of the best shows currently on the air. Given that result, it seems
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like the changes Stiller underwent in his time off were for the best, and his decision to explore
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stories outside of comedies was a wise one. I love directing. I would be very happy to do this
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as long as I can do it. It's a professional transition very few performers have been able
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to make work, and it's really impressive that Stiller pulled it off, especially given how deeply
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he was associated with some very specific comedic archetypes of the 1990s and 2000s. And to be clear
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Stiller doesn't regret that. Looking back over his career, he has said
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It's only in retrospect that I can go, Wow, there was a thing happening that I was fortunate to be a part of
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You can look at 2000's comedies, and they were a specific kind of thing, a tone
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and there were a lot of great things in those comedies that we don't have now. He even returned to starring in comedies in 2024 by playing the lead role in David Gordon Green's Nutcrackers
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I farted. He farted. Oh, come on. No piece of poop. The bottom line is that when he was faced with failure, Stiller decided to follow his truth and pursue projects that were more genuinely interesting to him
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And more in line with the kind of artist he's always seen himself as
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Enduring a professionally embarrassing box office bomb at the same time as a personally devastating separation from one's spouse would be enough to drag anyone down
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But for Ben Stiller, it turned out to be an exciting second chapter in an already storied career
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My joy comes from working and being creative, being creative, but sharing that with my family
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I'm so much more appreciative of it