In conversation, Buress is even more casual than he is on stage, a demeanor that signals his confidence, but also belies the fact that he's worked his ass off over the last decade to get himself on the doorstep of national fame.

He has served as a staff writer for Saturday Night Live and 30 Rock, is the co-host of the cult hit Eric Andre Show on Adult Swim, and is in the final stages of prepping a third live stand-up album (and second special for Comedy Central). Buress also has a growing portfolio of acting roles, including parts in the upcoming Zac Efron–Seth Rogen comedy The Neighbors and regular roles in the new Comedy Central show Broad City and the upcoming FX cartoon Chozen. And he's got his own pilot in production, also at Comedy Central, where he has an overall deal that has turned him into the network's jack of all trades.

Buress fits the profile of the modern comedian: In an era saturated with seemingly unlimited outlets spread across more mediums than ever before, piercing the dull buzz of endless options requires a wide range of talents and ability to pivot between every format imaginable. The diversity of Buress' résumé is especially impressive, considering he didn't begin even thinking about working in comedy until the moment he actually began working in comedy, when he decided to walk up to the stage at a college open-mic night.

It was the first risk in a career that has been defined, and greatly rewarded, by taking chances.

Before that fateful evening at Southern Illinois University, Buress' experience with crowds was limited to the football field, where he played special teams in high school ("I had no stats: no tackles, no catches, no rushing yards," he joked) and the scholastic debate club. But the moment he picked up the microphone at that little college talent show, he stepped into his future.

Comedy, and the pull of the stage, consumed him. His educational pursuits were rendered academic, and so Buress dropped out of school to focus on his act, shuttling back and forth between his parents' home in Chicago and wherever he could crash in New York City.

That was risk number two.

"I remember my first bit that I really liked and I thought was a killer: What if Jesus got high?" Buress said, laughing at those heady early days. "Would he be all philosophical, like, Oh, I always thought Joseph was my real dad, and My birthday isn't even on December 25? That was my first one that I thought would kill, and it did kill, and I loved it."

He still pokes plenty of fun at religion (much to his mother's chagrin), but Buress' routine has also expanded with age. Largely apolitical, his set generally consists of stories about dating (and failing at it), observational quips ("When people go through something rough in life, they say, 'I'm taking it one day at a time.' Yes, so is everybody. Because that's how time works"), reassessment of the mundane (he's got a popular bit about pickle juice), and good-spirited breakdowns of pop culture insanity (rappers beware).

More or less, he's focusing on everyday experiences and inanities, often with a detached bemusement. As Birbiglia noted, "He just is what he is. He's a brilliant joke writer. He comes on stage, and he's sharing it with you in this way that's kind of like, take it or leave it. You guys want some jokes? Here's some jokes."

But Buress has a kind of on-stage cool that is hard-earned, the sort of self-assurance built up over tens of thousands of miles and nonstop repetition.

By the summer of 2006, Buress' public profile (if not his bank account) was on the rise. He was still making sandwiches at Pita Pit, but he had also snagged spots in events of increasing credibility, like a comedy festival in Las Vegas and an NBC Stand-Up for Diversity showcase. He also had a good grip on the layout of the New York comedy scene. After arriving in Manhattan for one of his last visits as an outsider, the hustling would-be headliner made a beeline from Penn Station to three different open-mic spots…and then dropped in on his sister, who was raising a newborn baby in a small two-bedroom apartment.

That arrangement didn't work out — "I didn't even call her to say I was visiting New York; I just popped up with suitcases, and I came home late as shit" — and so he cleared out, sleeping on subways when necessary.

Call that risk number three.

"You just ride back and forth. People didn't wake me up that much," Buress recalled, shrugging and downplaying any danger he might have faced. "I'd go to bed, that shit was empty. And I woke up, people would be dressed up for work around me."

Older and wiser, the comedian tends to blanche whenever someone tries to mythologize his days crashing in subway cars, as if it were some big sacrifice made by a true dreamer. "It was just me being a stubborn 23-year-old," he insists. Either way, the hustle and extended hours spent kicking it in the makeshift MTA motel paid off, as the endless club hustle earned him his first huge opportunity: an invitation to sling some jokes at the famed Just for Laughs festival in Montreal, which begat his first TV appearance…in Amsterdam.