Sessa is admittedly a little itchy to move past the retro bildungsromans now. “I’m kind of done with the ’70s,” he says, laughing. (To be fair: He really has ’70s Face.) “It’s not that I want to be playing these mopey teenage boys all the time.” But in the meantime, as his next chapter comes into focus, Sessa is the best big-screen avatar for the perils of young manhood that we have right now.
One key to his genius at this particular type of role? He’s also living it in real time. “It’s that feeling of, like, you’re young and it’s okay to not know,” he says. “It’s okay to not have a clear direction. But I have the sense of wanting to feel that way, so it gets the best of you sometimes.”
If The Holdovers hadn’t turned him into an overnight sensation, Sessa had a few different career paths in mind: plastic surgeon, teacher, finance guy. When he’s really being honest with himself, though, Sessa admits that he’s always had something of a performative streak. Growing up in southern New Jersey, that manifested itself in a bunch of different ways. “I feel bad for my parents now,” he says, “because I just wanted so much attention all the time and would do anything to get it.” That included running around the house butt naked and singing at the top of his lungs, before his folks decided to channel that energy into extracurriculars—first dance classes, and then ice hockey.
He got good enough at the sport that—not long after his dad died suddenly at 46, when Sessa was just 14—he was accepted to the prestigious Massachusetts boarding school Deerfield Academy on an athletic scholarship. Just weeks before his first hockey season, though, Sessa suffered a career-ending femur injury. That led him to fall back on his natural talent for getting a laugh.
“At my high school, you were either the kid of someone really rich or famous, or you were a varsity lacrosse player,” Sessa says. “I was neither of those things, so I knew I had to kind of be the class clown.” His sense of humor was shaped, in large part, by the slew of Jackass and Sacha Baron Cohen movies his dad showed him at an (arguably too) early age.
Before long, he fell headfirst into Deerfield’s theater productions, and by the time his senior year rolled around, he found himself cast in The Holdovers with the prospect of a real career as an actor suddenly on the horizon.
The Holdovers dropped Sessa right into the center of the Hollywood buzz machine, shuffling him through a gauntlet of red carpets and award ceremonies as critics breathlessly compared him to The Graduate–era Dustin Hoffman. “It was so gratifying,” he says. “But even at that time I still had stress about, like, ‘Can I still do this? Can I even do another movie? Was this just a fluke?’”
The three films he made in quick succession after that awards run helped assuage those fears: the Rose Byrne vehicle Tow, in which Sessa aged up as a sympathetic lawyer; Michael Showalter’s holiday romp Oh. What. Fun., which let him flex his comedic instincts; and Now You See Me: Now You Don’t, where he got to smoke a joint in Woody Harrelson’s trailer and get career advice from Jesse Eisenberg. “He really made a point about just living in the moment, enjoying it, taking things as they come, because anything can happen in this industry,” Sessa says of the latter. “We’re so lucky to be able to do this, so don’t treat it like shit.”
