In two movies this fall, can be seen pushing himself in new directions as an actor, finding idiosyncratic, serio-comic tones to explore characters who find themselves in midlife crises and at crossroads perhaps not so far from where Stiller may currently also find himself.
In both “Brad’s Status” and “The Meyerowitz Stories (New and Selected),” Stiller plays men at a moment of self-reflection and reassessment, taking stock of their lives. Both performances have a richness of character detail, a nuance of emotion and are shaded by subtle comedic underpinnings.
Admitting he didn’t at first naturally connect the two roles himself, Stiller noted how it has become meaningful to him that in “Brad’s Status,” written and directed by Mike White, he plays a father struggling to relate to his son, and in “The Meyerowitz Stories,” written and directed by Noah Baumbach, he plays a son trying to get closer to his father.
“That was the delineation I think that I felt,” he said, “and I happened to be at a place in life where I have an older father and I have a young son, so there’s that place where you’re dealing with both and figuring out how to navigate that. And I felt like each movie had a different aspect of being a father or being a son.”
Stiller is talking on the phone while sitting in the back of a car somewhere in Yonkers, N.Y., in the middle of a tech scout for “Escape at Dannemora,” an eight-part Showtime series he is directing that stars , Patricia Arquette and Paul Dano and tells the story of a 2015 prison break in upstate New York.
The last few years ave been particularly tumultuous for Stiller both personally and professionally. He dealt with prostate cancer in 2014. His mother, actress Anne Meara, died in 2015. Earlier this year, Stiller and Christine Taylor, his wife of 17 years, announced their separation. (The couple have two children.) And last year, “Zoolander 2,” which he directed, produced, co-wrote and starred in, came out to withering reviews and box office disappointment.
For “Brad’s Status,” Stiller got the script by mistake. He was supposed to be receiving the script for a CGI children’s film White had written but instead was sent the story of a man coming to terms with his life as he takes his high school-age son on a tour of potential colleges while also grappling with the outsize successes of his own old college buddies.
White did not write the part with Stiller in mind, but once the actor had read the script and became interested, White became hooked by the notion too.
“There is an element that feels like a Ben Stiller vehicle. [With the character’s] urban anxiety and ambition — he is somebody who obviously comes to mind,” said White. “And I knew that he would do a great job, but also because the movie has some melancholy, some different tones than I’ve seen from him, it seemed like it might be exciting to present him in a way that seems like a more familiar Ben Stiller movie and then kind of subverts that with more existential dread.”
Stiller, 51, is known as a comedic superstar with movies such as the “Meet the Parents” series, the “Night at the Museum” franchise and the “Madagascar” animated films all to his credit. He has also directed pictures of incredible ambition and scale: the war movie send-up “Tropic Thunder” and the action-fantasy romance “The Secret Life of Walter Mitty.” So to see Stiller explore uncertainty and self-doubt with such knowing depth can be a bit of a surprise.
“I do feel like everybody can connect to that,” said Stiller. “I think we all have those same feelings to a certain extent, no matter how people might perceive you from the outside.”
Baumbach wrote the part of the driven, successful business manager in “The Meyerowitz Stories” with Stiller very much in mind, and he did the same for in the part of his underachieving sad-sack brother. In the film, the two compete for the attention of their father, a sculptor who’s never received the acclaim he feels he deserves, played by Dustin Hoffman. Baumbach said the first few people he showed the script to, including Stiller, thought the roles of the brothers were intended for the opposite actor.
“I felt like it was an opportunity for Ben to play something closer to who he really is,” Baumbach said. “And when Ben clicked into that, I think it was very gutsy of him to reveal that on-screen.”
“The Meyerowitz Stories” is the third film Baumbach and Stiller have collaborated on, following “Greenberg” and “While We’re Young.” Stiller now seems fully attuned to the specific rhythms of Baumbach’s writing, the movement and blocking that happens within the shots, and the subtle shifts in tone that can occur within a scene.
“My movies tend to not delineate what’s funny and what isn’t. Which I’ve heard as both praise and a criticism. But I like it. I like for that stuff to exist simultaneously,” Baumbach said. “But it’s something that he understands implicitly, and because he’s a comic as well as a terrific actor, he can innately convey both at the same time. Which is one of the many reasons I like working with him and why I think he works very well with my material.”
But now, Stiller has to get back to his tech scout — “I’m going to go in the sewer tunnel now,” he said dryly by way of a sign-off — making time for one final question before he does. Given that these two films have an air of midlife reassessment and considering how much he has been through in the last few years, has it all brought him to a new perspective on himself?
“Sure, that’s a totally valid point,” he replied. “I feel like I’m at a place right now where I’ve wanted to get to for a long time personally in terms of where I know the work that I’m doing is just about something that I find personal and creatively challenging and that’s it.
“Without getting into it too much, I have been around for a while and been through a lot of ups and downs, and I feel really fortunate to have that sense of myself now, that what I’m doing creatively can connect with me somehow inside. That’s really important to me. And how you get to that — whatever your own personal thing is — that’s where I’m at right now.”
This story is part of The Times’ fall 2017 movie preview. Check out the .