Jason Segel Has Mastered Comedy. Now, He’s Digging Deeper.

Jason Segel has always been a goofball. The charming, 6-foot-4 fixture in Judd Apatow’s universe writes, produces and stars in mostly comedies. 

As a teen, Segel was a cast member of the critically acclaimed yet short-lived “Freaks and Geeks” before eventually appearing in other Apatow projects like “Knocked Up,” “Get Him To The Greek” and “This Is 40.” In between his series regular role as Marshall Eriksen on the CBS sitcom “How I Met Your Mother,” Segel penned a few scripts, including 2008′s “Forgetting Sarah Marshall,” in which a heartbroken composer (Segel) takes a vacation to Hawaii to process his recent breakup, only to discover his ex (Kristen Bell) is at the same resort with her new rockstar boyfriend (Russell Brand). Many noted Segel’s originality ― he composed and performed a Dracula puppet musical to wrap up the rom-com ― with The New York Times saying the breakup comedy did not “entirely play by the established conventions of its genre.”

But lately, Segel’s been searching for something deeper. 

In his late 30s, he found himself turning away from his tried-and-true genre, realizing he was making films he wouldn’t actually want to watch. 

“I reached a point of doing 10 or 15 years of a lot of really great comedy and, don’t get me wrong, I loved every minute of it … but I’m not exploring anything that I’m actually going through in my real life anymore. I’m exploring stuff that 24-year-old me was thinking about, still,” Segel said when I sat down with him over Zoom last week. 

That might explain why he’s confidently tossing his hat into the exclusive “Drama Actors” ring, his most recent role being that of Dane Faucheux in Gabriela Cowperthwaite’s “Our Friend,” in theaters and on demand Friday. 

“Our Friend” is based on a 2015 Esquire essay by widower Matthew Teague, who lost his 34-year-old wife Nicole to a battle with cancer. In the piece, Teague not only details Nicole’s diagnosis but pays tribute to their best friend, Dane, who dropped everything and moved from New Orleans to Fairhope, Alabama, to help take care of the couple’s two daughters. 

When casting the lovable yet internally conflicted Dane, Cowperthwaite had one person in mind: Jason Segel. 

“He obviously understands comedy probably better than anybody, but, for me, it’s this reservoir of emotion and sometimes darkness, sometimes even pain, that I can see, in his eyes,” she told HuffPost of the actor.

When I mentioned the comment to Segel, he laughed, questioning whether he should consider therapy. “None of us are just one thing,” he continued. “We all get food pellets from the universe for different parts of our personality, and mine was comedy. And so, you lean into that, and then the parts of you that aren’t being serviced probably start to try to leak out through the ol’ eyeholes.”

Cowperthwaite, best known for the 2013 documentary “Blackfish,” said Segel’s performance in “The End of the Tour” sealed the decision to pursue him for her second narrative feature. He impressed critics and audiences as David Foster Wallace in the 2015 indie, which chronicles the five-day interview between Rolling Stone reporter David Lipsky (Jesse Eisenberg) and Wallace right after the 1996 publication of Wallace’s magnum opus, “Infinite Jest.” Segel nabbed an Independent Spirit Award for Best Male Lead and was on a lot of Oscar shortlists. 

“The idea that the same person did that and ‘Forgetting Sarah Marshall,’ just, Jason can just go back and forth so seamlessly,” Cowperthwaite added.

Segel is familiar with the “funny guy goes serious” tale. He’s also familiar with the docket of “15 or so” names usually in the running to claim more high-profile roles. It took him a while to get casting agents to consider him for something other than comedies, but now that he’s opened his well of emotions, he’s not afraid to take risks. 

With “Our Friend,” Segel appreciated that he could infuse his humor into an intimate portrayal of a man dealing with grief and insecurity. Dane is the light of the story as well as a reminder that everyone is struggling in one way or another. Working a humdrum job at a retail store with no career prospects in sight, he leaves behind his unfulfilling life to move into the Teagues’ home and help Matt (Casey Affleck) as Nicole (Dakota Johnson) fights cancer. 

“This is a guy, very much like me in a way, who is there to make the room brighter, there to take the steam out of the vent. But when he goes home at night, he’s sad and dealing with this more complicated, rich, interior life,” Segel said. “I felt like I’d be good at that.” 

The film gave Segel the opportunity to flex all his creative muscles and work alongside longtime friend Johnson and Oscar-winning actor Affleck, who he says expects co-stars to be present and authentic in each and every frame.  

“Casey is really, I think intentionally on his part, very unsteady,” Segel explained. “Casey’s gonna do what he wants, and I mean that as a huge compliment. I didn’t really have a choice to make a plan. He very well may say in character, ‘Why are you doing that?’ And then you’re f ― I almost said a swear word, but yeah. You’re taking little bits and putting them in your toolbox.” 

Segel gives a warm, magnetic performance in an ensemble piece that will surely get those ol’ eyeholes flowing. As a documentarian, Cowperthwaite’s goal was to make the story feel as palpable as possible.

“We weren’t focused directly on the disease in question and what that means to that person, we were looking at the friend, who, right when the bottom drops out from your life and you’re going to fall, someone’s sort of throwing a pillow there to cushion it,” Cowperthwaite said. “It was shifting the perspective from the pure appearance of the grief to the anchor ― the person that’s anchoring you and making sure you don’t fall too far.” 

At 41, Segel is no longer just the onscreen, broken-hearted boyfriend. He’s made an effort to try new things (“The Discovery,” “Come Sunday”) and works with people he admires to pick their brains about longevity in the industry. 

“I asked a buddy, a really great actor, ‘How do you choose stuff? What do you think the point of all this is?’ And he said, ‘Art is performing an act of self-exploration on behalf of an audience.’ And I thought that was a really amazing model of how to choose or write stuff that I have never thought of,” Segel said. “[Instead of], ‘What will be funny? What will make a lot of money? What will be popular?’ I started to look at people that I admire and it’s just that ― they’re exploring a subject on behalf of all of us.”

That motivated Segel to create and star in “Dispatches From Elsewhere,” an anthology series that debuted on AMC in March. It co-stars Sally Field, Richard E. Grant, André 3000 and Eve Lindley and follows four people whose eyes are opened to a world of possibility and magic when they stumble across a puzzle hiding just beyond the veil of everyday life.

“I just went right at all of these things that I had been thinking about,” he said of the show’s premise. “I feel like we’re probably all lonely and rarely talk about it, and we all feel, like, so unique in our loneliness. If only we just all said that we’re lonely, maybe we could all be free of that idea? That was just really interesting to me to find out if that was true, like, if I say this, will anyone else say, ‘Me too’?” 

Next up, Segel, who is also an accomplished co-author of the “Otherworld” and “Nightmare!” book series, will star in Josephine Decker’s Apple original “The Sky Is Everywhere.” And he continues to write every day while mostly at home due to the pandemic.

“I’ve written more than I’ve written in a really long time, and thought about what I wanted to do,” he said. “There’s a great expression, ‘A crisis is a terrible thing to waste.’ How are you going to emerge from a period like this? Are you going to have learned something and emerge changed? Or is it just gonna be like you hibernated and made it through? I think one of the things that we’ve had the opportunity to do is really look at what was working and what wasn’t working in our lives. When you strip away all the BS, like, ‘Oh, is this making me happy?’ I ended up making a lot of changes based on that criteria.” 

“Our Friend” is in theaters and on demand Jan. 22.