The late 2000s: They were the best of times, they were the absolute worst of times.

Although this period marked the glory days of the oft-romanticized blog era and a time before Karmaloop’s Chapter 11 filing and revival, it also saw the playbook for an entire way of life rewritten by the recession. Imbued with the optimism of Barack Obama’s historic presidential election in 2008, many resolved to figure it out by betting on themselves—existential dread and all. How to Make It in America, which premiered on HBO in February 2010, was guided by this spirit.

Created by writer/producer/director Ian Edelman, How to Make It in America peered into the lives of 20-somethings sorting through the mess in New York City at the turn of the decade. Ben Epstein (Bryan Greenberg) was the moody artist who couldn’t get out of his own way. Cameron Calderon (Victor Rasuk) was a natural hustler and the yin to Ben’s yang. On a “fuck it” impulse, the duo founded a clothing brand, Crisp, which was inspired by 1970s New York City. 

How to Make It in America was certainly not for everyone. GQ cut it down for signaling “cool” without earning the distinction. A HuffPost critique frankly dismissed it as “a gimmick.” Criticism notwithstanding, How to Make It in America resonated with kindred spirits, as many related to the insatiable desire to “make it” in myriad ways. HBO gave it a second season featuring a bigger budget, a wider purview, and higher stakes. There were more famous guest stars and high-profile cameos (Pharrell; Isaac Mizrahi; Pusha-T), but, above all, improved storylines and structure. 

And just like that, it was gone. 

HBO sent How to Make It in America to the gallows in December 2011, canceling it a month after the second season concluded. The cast has since joined fans in calling for a revival of some sort, as both the people responsible for making the show and the audience it captured seek closure. Did Ben remain his own worst enemy? Did the industry leave Cam jaded? Did Crisp survive the 2010s? Maybe we’ll get these answers one day, maybe we won’t. In the meantime, here’s the next best thing: The story of How to Make It in America, as told by the people who made it. 

Large play button icon