Josh Segarra Gets to the Heart of Hollywood: “I’ll Never Stop Being a Fan of This Business” (2024)

Josh Segarra could be Hollywood’s biggest fan. The actor, who has been working steadily for the past 15 years — first with day gigs like a scene in the Homeland pilot shortly after his graduation from NYU, later with recurring roles on Chicago P.D. and Orange Is the New Black — is effusive, bordering on glowing, about the business. He remembers details about every guest spot he’s ever done, every executive or star who’s helped him to where he is today. Claire Danes was “so sweet and kind” and did crossword puzzles on set; John Leguizamo was “awesome”; Kevin Bacon offered some banter about the New York Giants to calm some nerves. “It hasn’t been lost on me when somebody can tell I’ve got stars in my eyes and takes the time to give me a hug,” he says. “It’s why I’ll never stop being a fan of this business.”

It’s hard to pinpoint Segarra’s breakout role, and it’s likely most of his fans would offer differing answers. He did a season-long arc on Arrow and starred on Marvel’s She-Hulk: Attorney at Law, two franchises that offered the actor, who was not a comic book devotee beforehand, an education in dedicated viewership. “Once I booked those roles, I immediately started getting texts from people in my life saying, ‘Welcome to the party, but don’t mess this up,’ ” he recalls with a laugh.

Growing up near Orlando gave Segarra the chance to form his own fandom attachments, most from the pop culture of your standard semi-elder millennial. First, it was Nickelodeon’s nighttime comedy lineup SNICK — studio tours of the Orlando lot, including the set of All That, are a treasured pastime. Then he recited lines from raucous comedies like Tommy Boy and The Mask into the mirror. He learned about NYU’s prominence after Mary-Kate and Ashley Olsen announced their enrollment. Much like his mental Rolodex of generous co-stars, he has vivid memories of the people who early on helped him realize —and conceive of —his dream to become an actor. “I had a high-school teacher, Mrs. Mueller, who totally changed the trajectory of my life just from the way she taught us to treat the theater,” he says. “And my parents never made me think that there was anything I couldn’t do if I put my mind to it.”

This year, he’s been seen in Scream VI and The Big Door Prize, the Chris O’Dowd-starring Apple TV+ dramedy. But it’s The Other Two that he’s here, mostly, to talk about. The HBO Max comedy from former SNL writers Chris Kelly and Sarah Schneider centers on a Justin Bieber-like YouTube star turned mega-celebrity named Chase Dreams, whose momager (Molly Shannon) becomes famous in her own right.

Segarra, 36, plays Lance, a fashion designer dating Chase’s older sister and manager, Brooke (Heléne Yorke). He serves as the goofy antidote — he thinks it’s still cool to dab — to the show’s blistering roasts of celebrity-worship culture. Segarra is more suave than his onscreen counterpart, but they share the same good nature, especially when it comes to the source material. “I’m a Belieber. I saw [2011 concert film] Never Say Never in theaters,” he says. He isn’t sure Bieber has seen the show (“He’s got to at least know Molly Shannon”), but he welcomes the chance to open that door. “I’d definitely tell him he has to watch our little comedy,” he says. “I think he would appreciate what we have to say [about fame].”

Josh Segarra Gets to the Heart of Hollywood: “I’ll Never Stop Being a Fan of This Business” (3)

On the third season that premieres May 4, Lance finds a new calling as a nurse, having given up fashion design in order to “make a difference” after the pandemic — much to Brooke’s annoyance. She starts a spite-search for a new career “doing good” outside of the industry; in typical The Other Two absurdist fashion she becomes (literally) invisible to agents, managers and celebrities now that she’s a normie. Segarra is often awestruck by the lengths to which the jokes go, but has never felt nervous about a storyline’s reception. “It’s a testament to the creators’ genius that they know exactly where the line is,” he says. “But if only you could see our text messages when we get the scripts. I love watching them find humor in a place where other people haven’t yet.”

As soon as this interview wraps —and his Bloody Mary is finished — Segarra will fly back to Atlanta, where he’s already shooting the second season of The Big Door Prize. Where The Other Two is heart and bite, Prize is nearly all heart. Created by Schitt’s Creek alum David West Read, it takes place in a small town after a mysterious video game shows up at the general store; it dispenses cards detailing each player’s true life potential, often much to their dismay. Segarra offers his characteristically gushing sentiment here, too: “I was so excited to meet Chris O’Dowd, and he’s just been the coolest guy. That’s my buddy. I love him.” Episodes of the first season are still rolling out, so he can’t say much at all about what’s planned for this go-around beyond that it keeps building on the story of a town thrown off-kilter by its citizens’ dreams deferred or entirely unrealized. “The whole town is going through this midlife crisis together, and it’s kind of like what the world went through during the pandemic,” he says.

But there’s no midlife crisis at this breakfast table. Segarra is beyond content: with his role as a father, with the way his career is going, with the Bloody Mary. Despite the razor’s edge of the jokes that The Other Two delivers, and the dark elements of the business they potentially expose, he believes that the show is rooted in (what else?) a deep fandom, and that it’s all love. “Our business can get a haze on top of it,” he says. “And sometimes you’ve got to wipe it down clean to see the heart inside of it.”

A version of this story first appeared in the April 26 issue of The Hollywood Reporter magazine. Click here to subscribe.

Josh Segarra Gets to the Heart of Hollywood: “I’ll Never Stop Being a Fan of This Business” (2024)
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