“I think, for me, probably the biggest realization was how much I enjoyed directing and not acting at the same time,” says Ben Stiller as we sit down at the offices of The Hollywood Reporter to record an episode of THR‘s Awards Chatter podcast and begin discussing his Emmy-nominated work on the acclaimed Showtime limited series Escape at Dannemora. Of working on the project about a real 2015 prison break in upstate New York — which is Emmy-nominated, as are all of its aforementioned stars, and Stiller, for producing and directing — the 53-year-old continues, “It was really freeing for me. On the first day of shooting, I just had this feeling inside like, ‘Oh, this is really what I should be doing. I should not be trying to do both things at the same time.’ I still love acting, [but I love this, too]. And then not having the pressure of it being a comedy? It’s a whole different world. I had one of the best experiences I’ve ever had, working on it.”
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LISTEN: You can hear the entire interview below.
Past guests include Steven Spielberg, Oprah Winfrey, Lorne Michaels, Barbra Streisand, George Clooney, Meryl Streep, Robert De Niro, Jennifer Lawrence, Eddie Murphy, Gal Gadot, Warren Beatty, Angelina Jolie, Snoop Dogg, Jessica Chastain, Stephen Colbert, Reese Witherspoon, Aaron Sorkin, Margot Robbie, Ryan Reynolds, Nicole Kidman, Denzel Washington, Julia Louis-Dreyfus, Matthew McConaughey, Kate Winslet, Jimmy Kimmel, Natalie Portman, Chadwick Boseman, Jennifer Lopez, Ricky Gervais, Judi Dench, Quincy Jones, Jane Fonda, Tom Hanks, Amy Schumer, Justin Timberlake, Elisabeth Moss, RuPaul, Rachel Brosnahan, Jimmy Fallon, Kris Jenner, Michael Moore, Emilia Clarke, Lin-Manuel Miranda, Helen Mirren, Tyler Perry, Sally Field, Spike Lee, Lady Gaga, J.J. Abrams, Emma Stone, Ryan Murphy, Julia Roberts, Jerry Seinfeld, Dolly Parton, Will Smith, Taraji P. Henson, Sacha Baron Cohen, Carol Burnett and Norman Lear.
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Stiller, the son of Jerry Stiller and Anne Meara, one of the all-time great comedy teams, grew up with a serious sensibility. “As a kid, I was sort of trying to find my own way,” he says, noting that he spent much of his childhood shooting Super 8 movies and reading American Cinematographer magazine. “And then eventually I came back to comedy, because I think it is genetically part of my makeup.”
After briefly studying at UCLA’s film school, Stiller dropped out and landed a small part in The House of Blue Leaves, a theatrical production which moved to Broadway in 1986. During his time backstage, Stiller made a pseudo-documentary short about the show’s lead, John Mahoney, which he showed at the cast party, and which went over well. “That was probably the first time I really thought I could do this,” he says of directing.
Around that time, Steven Spielberg saw Stiller in the show and cast him in 1987’s Empire of the Sun (for which Stiller lost 35 pounds). Not long after, Lorne Michaels saw a 16mm film that Stiller had made and hired him as a featured player on Saturday Night Live (he lasted just six weeks because, he says, “I just wasn’t that good at it”). And then MTV offered him the chance to make a half-hour variety sketch program, The Ben Stiller Show, which was later rebooted at Fox with Judd Apatow as his collaborator. It was short-lived, but it brought Stiller a writing Emmy in 1993, and a host of other opportunities.
Stiller directed and played supporting parts in Reality Bites (1994), an indie sensation, and The Cable Guy (1996), a big-budget flop (on which he first crossed paths with frequent collaborator Owen Wilson). In 1996, he also played a small part in Happy Gilmore, opposite Adam Sandler, and a big part in David O. Russell’s Flirting With Disaster, opposite Patricia Arquette.
Post-Cable Guy, when Stiller’s stock as a director was lowest, he was approached about starring in a comedic film unlike anything he had done before: Peter Farrelly and Bobby Farrelly‘s There’s Something About Mary. “I remember reading the script and laughing out loud and thinking, ‘This movie is either going to be one of the funniest movies ever or it will be horrific,'” he says with a chuckle. “And it was, luckily, I think, the former.'”
Despite the reluctance of 20th Century Fox, Stiller was cast as Ted opposite Cameron Diaz‘s Mary, and the film — which includes scenes involving a zipper and “hair gel” that are now considered classics — was released in the summer of 1998 and became a global sensation. Stiller recalls, “It was the first time that I’d ever been a part of anything, either as a director or actor, where people just kept on coming up and going, ‘That movie’s so funny!’ I was like, ‘Oh, cool!'”
Mary made Stiller a star, which came with its own complications. “It was the first time I was ever in a movie that made money, and that was an interesting experience because it really does change things for you as an actor, not necessarily for the better,” he explains. “Up to that point, I really was happy. I was having fun. And then all of a sudden it was another world of box office and all that stuff.” He continues, “It was definitely something I wasn’t used to and I don’t think I knew how to navigate it. All of a sudden, people were bringing movies to me and saying, ‘Hey, they’ll do this movie — if you say yes to it.'”
The problem was that the only films people seemed to want to make with Stiller were others in which he would portray a goofball man-child experiencing broad physical humiliations — plus, pressure to “open” a movie now fell on him. He made many such movies over the ensuing years, several very popular, including Meet the Parents (2000), Zoolander (2001), Along Came Polly (2004), Dodgeball: A True Underdog Story (2004), Starsky & Hutch (2004), Tropic Thunder (2008) and Tower Heist (2011), plus a couple of kid-friendly franchises, which originated with Madagascar (2005) and Night at the Museum (2006). But he was not content.
“I was wrestling with it, for sure,” says Stiller. “It was something that I didn’t feel that great about at the time.” He elaborates, “I don’t think I didn’t want to do them; I think what it was was that I wasn’t prepared for them to have that much of an impact that there would then be this sort of — not a backlash, but people saying, ‘Well, that’s what this guy is.'” He adds, “My sense of humor was not as much that mainstream kind of thing. [It was] weirder stuff. As I did these other kinds of comedies, I was sort of trying to figure out my own identity.”
Stiller began to gravitate towards roles that were different — darker and more eccentric — several in indies directed by Noah Baumbach — Greenberg (2010), While We’re Young (2014) and The Meyerowitz Stories (New and Selected) (2017) — on which Stiller didn’t feel the same sort of box office responsibility that he did on studio films. As for studio films, he increasingly signed up for them only to get studios to give him a chance to direct them, too — that was the case with Zoolander, Tropic Thunder (the most expensive R-rated movie ever, and one so politically incorrect that Stiller says, “I don’t think it would have gotten made today, for sure. … It’s a totally different world today”) and 2013’s The Secret Life of Walter Mitty.
In 2014, Stiller — the father of two children with actress Christine Taylor, from whom he separated in 2017 — was diagnosed with prostate cancer. “It’s that moment in time when you go, ‘Oh, my God, there’s nothing if I’m not around, and how do I go forward with that?'” he says. By 2016, Stiller was given a clean bill of health — “I was really, really lucky,” he acknowledges — and it seems that, at that time, he was as clear as ever that he would henceforth only take on the sorts of projects that creatively fulfilled him.
That is in no small part how he wound up directing all seven installments of Dannemora — totaling eight hours of screen time, the equivalent of five or six feature films — while leaving on-camera duties to Benicio Del Toro and Paul Dano, who play prison inmates, and his old pal Arquette, who plays the prison guard that helps them try to escape. Stiller’s direction of the series has been hailed as revelatory, not least a nine-minute tracking shot that opens the fifth installment, which was shot over six months and features 17 different shots seamlessly stitched together.
“Sure, it was scary,” he says of the project, which was partially shot inside the actual Clinton Correctional Facility from which the inmates escaped, and was unlike anything Stiller had ever done before. “But whether or not people would accept that I could do it was not something that I thought about a lot. As we went through the process, people would be like, ‘Oh, it’s weird you’re doing this’ or ‘Wow, it’s great you’re doing this’ or ‘You know, that’s different for you!’ And, in my mind, I hadn’t really thought of it that way, because I’ve always loved directing, and in my head I was like, ‘Yeah, I’m gonna make something like this,’ and I just never had done it. And then the actual process of doing it felt really good and really natural.”