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Photograph: Anna Schori; Jacket: Marc Jacobs; T-Shirt: Earnest Sewn; Jeans: Rag & Bone

The HBO hit How to Make It in America has taken Bryan Greenberg’s career to new heights — and new countries.

“I’m so sick of being cool and broke,” Bryan Greenberg says between bites of a banana. “Like, I want to get paid. I want to be big.”

He’s relating the newly adopted mindset of Ben Epstein — the character he plays on HBO’s How to Make It in America, which kicks off its sophomore season next month — but he could just as easily be talking about himself a decade ago when he was still a struggling actor.
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Photograph: Anna Schori; Suit: Shipley & Halmos; Shirt: Burberry London

The parallels aren’t lost on the 33-year-old St. Louis native. Like Ben, an aspiring fashion designer forced to make ends meet in other ways, Greenberg endured his fair share of odd jobs — waiting tables, tending bar, working for a mortgage broker “helping other people buy their dream houses” while he could barely cover his own rent — before landing breakout roles in movies like Prime and on shows like One Tree Hill. Greenberg also shares his character’s understated approach to success, preferring quiet determination to shameless self-­promotion. “I’m not good at the schmoozing thing,” he says. “I do the work and try to let it speak for itself.”

But while Ben frequents hip parties in Manhattan lofts packed with willowy model types, ­Greenberg’s early experience in the Big Apple, where he attended NYU’s Tisch School of the Arts before decamping to L.A., wasn’t nearly so glamorous. “I was at those parties,” he says with a laugh. “But I was catering.”

He also admits to being considerably less style-savvy than his on-screen counterpart, though his ready familiarity with the designer brands on hand at his American Way photo shoot forced him to acknowledge that his character’s sartorial sensibilities had started to rub off on him. “I’m a jeans-and–T-shirts guy,” he confesses. “I’m learning how to dress just from being on the show.”

Another bonus: getting to co-star with rapper/actor Scott “Kid Cudi” Mescudi, who earlier this year lent his musical talents to Greenberg’s second self-released album, We Don’t Have Forever. That’s right, Greenberg sings too — a hobby that he says affords him a unique perspective on fame.
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“I get to go on the road and meet fans in Iowa or Minnesota, and most actors don’t know what that’s all about,” he says. “I was on tour in Toronto and Vancouver, and they were loving How to Make It. I didn’t even know it was on there!”

Perhaps that’s where Greenberg differs the most from his character: He’s got no plans of stopping at the 50 states.