Jason Segel had won–hadn’t he?
He’d won in his early 20s, when he made a universally acclaimed film, Forgetting Sarah Marshall, establishing him not only as one of the key comedic voices of his generation both in front of and behind the camera. He won again when he followed it up quickly with a beloved role one of the most successful sitcoms of the century thus far—How I Met Your Mother.
Why didn’t any of it feel like winning?
“I had a really intense period of success in my 20s, up into my early 30s. When I hit 33, and How I Met Your Mother ended, it was the first time in my career since that period started where I had a minute to think, and breathe,” he tells Esquire Middle East.
“One of the things that I really realized was, by most people’s standards, I had sort of won. But I was very unhappy. I was not feeling the thing I was told I would feel if I had achieved all these things.”
Segel wasn’t sure what to think. After all—he’d done everything right–or more accurately, he’d done what he was told. But whatever it was wasn’t what he wanted. Frustrated, he started to think back to who he was when he wrote Forgetting Sarah Marshall.
“When I wrote Forgetting Sarah Marshall, I was 24 years old. And it was very authentic to what I was going through at the time. I just had a big break up, I was having really intense feelings about it, and I wanted to express that,” he says.
“What I didn’t understand is that, that what then happens, if you’re not careful, because this is a business, is take that success and stretch it as far as you can until the rubber band snaps.”
While he was stretching the rubber band on the film side, as much as he enjoyed the experience of making How I Met Your Mother, that show felt as stretched as thin as he was.
“It’s wonderful that it went nine seasons, but I don’t know that this is a nine-year story that needed to be told. You find ways to keep it going,” he says.
Segel had been consumed by commercial success, listening to everyone in his life that told him what the right business moves are, and lost touch with his own artistic impulses—and thus himself.
“I realized that I hadn’t done an artistic check-in since I was 24 years old. I looked at what I was making, and what I was writing, and it wasn’t really fair to call it art anymore, if art requires some amount of self-exploration,” Segel continues.
“I realize this sounds a bit artsy-fartsy,” he laughs.
Jason Segel moves forward
Segel then stopped answering the phone calls for parts that were exactly like the ones he’d been taking for the last 10 years, regardless of the amount of steady work it would afford him. After all, it didn’t allow him to grow, what was the point?
“I decided I was only going to take parts that put me near people that I admired, so that I could ask them questions about how they do it, and how they choose parts and—really reductive things,” Segel says.
“I wanted to ask the people I respected the most, ‘how long do you wait between roles? Do you think about money when you’re choosing your parts? Like, how do you do it?’ Because I had I really didn’t have an education in that way,” he continues.
“I came out of the gate, weirdly, making big studio comedies, which is a very particular thing. They sort of don’t exist anymore now.”
Segel is 42 now—nearly 9 years removed of the end of How I Met Your Mother, and since then, he’s stayed true to his word. Gone are the raunchy comedies that made him a household name. 2015 saw him take on the lead role as controversial real-life author David Foster Wallace in The End of the Tour, a performance that garnered him an Independent Spirit Award nomination for Best Male Lead.
From 2015 to 2020, he took on only three roles—The Discovery, Come Sunday, and Our Friend, each which tested him in different ways, before taking on the 10-episode series Dispatches from Elsewhere in 2020, a starring vehicle that was first thing he’d written since 2014’s Sex Tape. It was the herald of the new Jason Segel, a Jason Segel who had looked deeply at himself, and, in his own words, could finally make art again.
In 2022, Segel seems to be finally ready for another close up. This month will see the release of two major project from Segel—one his Netflix original film Windfall, starring Segel, Jesse Plemons and Lily Collins, from a story conceived by himself, Andrew Kevin Walker (Se7en), and the team behind The Discovery, Charlie McDowell and Justin Lader.
He’s also taken a key role in the excellent new HBO series Winning Time: The Rise of the Lakers Dynasty, streaming exclusively on OSN in the region, as ‘The Professor’ Paul Westhead, the American basketball coach with a penchant for quoting Shakespeare who led Magic Johnson and company to a championship in 1980.
Much like many of the Lakers teams of the 80s, the cast and crew is a murder’s row of talent—something Segel found too enticing to pass up.
“When I got sent the script, there were 15 people I admired in this cast that I was going to get to be near and ask questions to, and act alongside, and watch what they’re like when they’re between scenes, watch how they prep, watch how they act. Those are all things I want. That’s sort of what I’m all about at this stage of my career,” he says.
“I’m trying to—man, I’m trying to not miss it.”
“I always thought that it was about this final product, and how well it did or XYZ. Another neat thing about everything switching into TV is that these metrics of how well it does have sort of gone away. There’s just so much content. For me, it’s now about trying to not forget that this is my life. The making of this, the 10 months it takes to make this, is when I’m alive and it’s part of my life. It’s not bracketed from life—it is my life. I want to experience that. I want to act with Tracy Letts, I wanted to act with Adrian Brody, and all these people who I admire and want to learn from,” he continues.
There was also something in the character of Westhead himself—something that echoed the characters he’d once created in his broad comedy days that he couldn’t stop thinking about.
“I have done and have written also a lot of different versions of coming of age stories, and someone who is stepping into their adulthood. In a lot of ways, it’s what the style of comedy that I came up in was all about, for a long time. And comedy changes, as always. It always has. And that story, I think, had been told enough that it got left behind,” he says.
“When this came my way, it was presented to me in a more Shakespearean context, but in the same vein of somebody stepping into their manhood. I was really interested in approaching that same story at 42 that I had looked at when I was 25.”
“Paul Westhead, when we find him, is stuck. He’s stuck in a place that for most people is past the point of no return. As a younger guy who’s stuck, there is some hope that they’re just looking for their thing. Paul Westhead knew what his thing was, and it just didn’t take. They took away his coaching status. He was sort of relegated to purgatory of teaching Shakespeare, and thought that was going to be forever. And then circumstance forced him to step up. That was really interesting, somebody going to step up for what is probably their last at bat for glory,” Segel says.
Winning Time is now streaming exclusively on OSN in the Middle East. Watch here.