“Do you like your job?”
That’s how my interview with Jason Segel begins — him beating me to the punch, asking the first question. It perfectly sets the tone. Because like me, he likes his job a lot.
“I don’t like the parts of my job that require permission. That’s why I started writing. No one can tell you no, no one can say you can’t,” says Segel. “The best piece of advice I got was to try to remove as many of the systems of permission along the way as you can.”
Segel has worked hard to get to this point. Currently, he’s promoting Apple TV+’s “Shrinking,” a dark comedy he leads and co-created with Bill Lawrence and Brett Goldstein. There’s freedom in working on a project as a co-creator, but that wasn’t always the case.
He got his start as strictly an actor, breaking through in 1999 with the role of Nick Andopolis in “Freaks and Geeks.” When the NBC series was axed after one season, Segel followed the advice of producer Judd Apatow: Write.
Five years later, he landed a leading role in CBS’ “How I Met Your Mother,” a sitcom he never thought would run for 208 episodes. He appeared in every single one, while simultaneously starring in box office hits, like “Knocked Up” and “I Love You, Man.” He wrote his first movie, “Forgetting Sarah Marshall,” just as “HIMYM” began. While writing allows him the most control, it’s acting that he finds to be the easiest.
“Writing’s a war between you and yourself. Every day you wake up, you’re the one who is choosing to write or not write, so there’s a bit of self-loathing built into it,” he says.
For acting, he’s able to fully prepare before filming begins. “The actual acting process to me is the most peaceful, simplest time of my life. Your job is to make sure you know your lines perfectly, and show up there on time,” he says — and he’s always prepared. “For everything else, someone else’s in charge — including the scene. You can’t really have too firm a plan, because then you’re not leaving space for what Harrison Ford’s going to do. If your plan is too firm, you’re not going to have the magic.”
Over the last two decades, Segel has had many shifts in his career — including those that came in 2014.
“I had a very natural life change moment when ‘How I Met Your Mother’ ended. That was a decade. It was like coming out of a tunnel, where you enter in one person, and then it was truly non-stop for about 10 years, and then you come out,” he says. “All of a sudden, you have — for the first time in a decade — three months off. I was like, ‘Oh, my gosh.’”
At the time, he realized that the movies he was writing and starring in — mostly about “being scared of girls in some capacity” — didn’t apply anymore. “I’m a man who is successful and doing well at his job,” he says, recalling looking at the mirror and asking, “Why are you still writing about a 24-year-old?”
It was also time to make a shift in who he was working with; it used to be all about working with his friends — and he’s got a lot of talented ones: Apatow, Paul Rudd, Jonah Hill, Seth Rogen. So he decided to make a change.
“I was on this track where every year, I was doing ‘How I Met Your Mother’ for eight months of the year, writing a movie during that year which would then shoot during the hiatus. It was amazing, but there wasn’t much time to think about approach or to be too conscious about stuff that I now look at. I wasn’t being as thoughtful as I am now,” he says. “Around 33, I realized I was going to shift from working with friends as the priority to working with people I admire, so that I could learn from them.”
For about seven years, he took roles strictly to learn from people he looked up to and made it his mission to learn from them by continuously asking questions.
“It was a weird decision, but it all led me to how I feel now when I’m acting in ‘Winning Time’ or ‘Shrinking.’ I feel as though I have built together a backpack of advice. I have a lot of different, really smart people’s words in the back of my head,” he says.
And now, he’s a bit of a mentor himself. On the set of “Shrinking,” young co-stars Lukita Maxwell and Luke Tennie asked him questions about the craft and the business.
“I have a teenage daughter on a TV show!” exclaims Segel, who enjoys playing the dad now after years of playing the bachelor. “You don’t want to be the dude at the singles bar with, like, an earring, an old Corvette and frosted tips. You don’t want to be the acting equivalent of that.”
But again, it took time to get there.
In 2020, Segel hit another pivotal point in his both his personal life and career. It’d been six years since he wrote something (“Sex Tape,” which he also starred in alongside Cameron Diaz), and that didn’t sit well.
“I was not sure that I could write anymore. I was not interested in the stuff that I was previously writing or known for writing or expected to write. Even when I would try, nothing interesting would happen. It may be the same stuff was happening, I just wasn’t interested anymore,” he says. “I wasn’t quite sure what the point of it was for me.”
Then he watched “The Institute,” a documentary about an alternate reality. The way it made him feel — and the questions that arose — inspired him.
“It felt playful, dangerous, spooky, alive, mysterious and provocative. It was making you ask yourself questions about what you want your experience of life to be like. I was like, these are the questions I’m asking myself. What this guy has created is what I am going through right now,” he says.
As he was puzzled by how to adapt it, the fear — “the degree of it being dumb was so possible” — is what drove him to create “Dispatches From Elsewhere.” While the AMC series only ran one season, that doesn’t matter. Steering the offbeat show was one of the toughest jobs he’s ever had, and one of the most meaningful.
Cult favorite “Freaks and Geeks” also only lasted one season. “Maybe these things are exactly the length they’re supposed to be,” he says now.
It’s unknown how long “Shrinking” will run, but Lawrence has storylines planned for at least three seasons. While focusing on grief — Segel’s Jimmy is finding a way to move forward as a single father after the death of his wife — it also explores the different ways of getting through it.
As Segel notes, it asks the question of how people can make real emotional progress.
That was important to dive into, especially with the world we live in today. Now, he says, people like to name their trauma or, as Segel puts it, what is inside their “backpack full of shit.”
“A lot of people think naming it is where you get to stop. They’re like, ‘I have this so I get to be an asshole,’” he laughs. “I have a lot of shit I could name, but I want to be happy. So what do I do to actually make progress in my life?”
But what’s the answer? For Segel — much like it is in the “Shrinking” universe — it’s about community and finding those who help you feel less alone with whatever you’re going through.
“Counter to what we think is an inspirational message, I actually think that finding out that you’re not so unique that nobody has gone through what you’ve gone through is a really heartening idea,” he says. “It’s pretty amazing when you find out there are people who have already walked the path for you who can give you a little roadmap.”
Every role Segel has taken on — from the naked Peter Bretter (“Forgetting Sarah Marshall”) to everyone’s favorite husband Marshall Eriksen (“How I Met Your Mother”) to messy therapist Jimmy Laird — has a piece of him inside it.
“When we were writing Jimmy, I said I want him to have Michael Keaton energy — that kind of I’m pretty sure that I can keep it together. But there’s a chance I can’t,” he says of his “Shrinking” character. “That’s kind of where that character is centered, where you’re just really, desperately trying for there not to be a scene.”
This interview took place before the writers strike began.