On The Road With Hannibal Buress, Comedy’s Most Respected Slacker

Hannibal Buress is about halfway through his second set of the night in Denver when he turns to his DJ, who is sitting a couple of feet behind him, fiddling with his turntables. "Hey Tony," he says with a subtle wince, "play some music." And then he walks offstage.

Nobody is expecting this, least of all Tony. But the DJ puts down his drink and searches for a song as the crowd begins to murmur. Is he coming back? Is this part of the act? Did you hear what happened in Philadelphia? Eventually, they accept the intermission as an expression of Hannibal's eccentricity. After all, how many comedians travel with their own DJ? There's also the fact that he's just told a joke, which he prefaced by warning that it was totally unrelated to the jokes that came before and or would come after it, about taking a handful of ejaculate to a palm reader and asking about his future.

This sudden exit wasn't part of Hannibal's routine when I last saw him, a few weeks earlier, performing a sold-out show in the Brooklyn Academy of Music's regal opera house. There was a triumphant swagger to Hannibal's every move that night, as longtime fans from his adopted borough marveled and delighted at how the comedian's droll, deadpan style had brought him here. He's been an underground favorite for years, the type of guy you would see around town at bars or concerts or hosting his D.I.Y. comedy showcase a few miles away at the Knitting Factory. Now, legends like Chris Rock and Louis C.K. tip him as the future of comedy. As Hannibal strolled across that vast, fabled stage in Brooklyn, it felt like an intermediary moment before the next level of fame, when he's starring in his own movies and playing arenas.

But right now he's here in Denver, midway through the second of ten sets spread across four nights at a club called Comedy Works, where he's taking a break of sorts from the seemingly endless theater tour that's had him criss-crossing the nation for months. It's a taxing schedule, but he kept adding gigs because people kept buying tickets. The only thing he didn't account for was Denver's altitude. Right now, Hannibal can't breathe. Escaping backstage, he fishes his inhaler out of his coat pocket, takes a few puffs, then shuffles back, as though nothing has happened.

"Three shows a night is a different kind of mental endurance," Hannibal sighs, after the set is properly over and he's back in the green room. Out in the main room, the Comedy Works staff worms their way through the aisles, picking up stray cups and straightening loose chairs. He's got one more show left to do tonight. Hannibal sits next to a heat lamp, his hood pulled over his eyes. The thin, cold air has rendered him a sluggish, perpetually thirsty version of his normal self. There's a bottle of Jameson, a bucket of beers and sodas, plates of quesadillas and fries. There's also a spread of fresh vegetables—the influence of past tours with the comparatively health-conscious Aziz Ansari—and a small bowl of diced pineapples—the influence, he chuckles, of Rick Ross. He drinks water instead of the whiskey or beer, for fear alcohol will exacerbate his dehydration. He's deliriously tired, barely audible. His friend Al Jackson, a Los Angeles comedian who's flown in for the opening slot of these Denver dates, asks if Hannibal wants him to make his set a bit longer, but Hannibal says he'll be fine.

It's hard to distinguish altitude-induced sluggishness from Hannibal's naturally subdued vibe. When he's not on stage, he's withdrawn and disarmingly quiet, almost to the point of seeming perpetually bored. As his friend and collaborator Eric Andre tells me later, "He's the lowest key on the piano." They met around 2006, back when they were just a couple of broke stand-ups taking any gigs they could get. "I loved his act," Andre recalls. "He had a real unique point of view. You would think the joke was going one place, and it would go another place." But what really drew him to Hannibal was his unusual charisma. Small talk seems to pain Hannibal. At one point backstage, a bizarre public access show on TV catches his attention. It's a low-budget music video that never quite evolves into the bad softcore porn everyone is expecting it to become. A fan who has wandered in seems troubled that we're watching something so awful. "How do you think I write jokes?" Hannibal answers impatiently. "By looking at shit." "What's your joke about it?" she challenges. He doesn't say anything to her for the rest of the night.

Things have been good lately for the 32-year-old. After short stints writing for Saturday Night Live and 30 Rock, Hannibal has found a home in front of the camera, acting in memorable supporting roles on Comedy Central's Broad City and Adult Swim's The Eric Andre Show. He's released three acclaimed comedy albums, including last year's Live from Chicago. And this spring, he'll finally star in his own series on Comedy Central.

But the thing he's most famous for is Bill Cosby. Last October, a fan uploaded a video of Hannibal onstage in Philadelphia joking about Cosby's pattern of alleged sexual assault and abuse. It wasn't bad enough that Cosby had somehow managed to sweep these claims under the rug for 14 years, Hannibal told the crowd. What made it even worse was Cosby's smug, annoyingly moralistic "old black man persona." "'Pull your pants up, black people. I was on TV in the '80s!'" he mocked. "Yeah, but you raped women, Bill Cosby. So, brings you down a couple notches." It's not as if these were fresh revelations. "You leave here and Google 'Bill Cosby rape,'" Hannibal said. "It's not funny. That shit has more results than 'Hannibal Buress.'" Ironically, a joke about the comedian's relative obscurity ended up making him unimaginably famous.

To those familiar with Hannibal's work, the bit captured something essential about his point of view as a comic, the way his jokes rely on bemusement, skepticism, a kind of made-you-think discomfort. But it also accomplished something unexpected, thanks to the capricious whims of the internet: for the first time, it really got people talking about the elder comedian's dark side. The ensuing controversy cost Cosby dearly: he lost an NBC series, a Netflix stand-up special was postponed, and reruns of The Cosby Show were taken off TV Land. To the Cosby loyalists that sent Hannibal hate mail and death threats, he seemed like an opportunistic, young black comic making his name by taking shots at a legend.

Hannibal's intention hadn't been to launch an international campaign—"I guess I want to just at least make it weird for you to watch Cosby Show reruns," he'd told the original crowd in Philadelphia. Between sets in Denver, when I ask him about the fallout, he still seems shaken, if not slightly irritated, by all the unwanted attention. Beyond describing the situation as "weird" about a dozen times in the course of a minute, he's not interested in revisiting it.

All of which brings us to the lonely grind of life on tour. The road is meritocratic: they either laugh or they don't. "There's more control," he says. "You don't have to run your ideas past anybody. You get to travel." The road is what drew him to comedy in the first place, back when he was starting out in Illinois, dreaming of doing three or four sets a night all across Manhattan. The road is where he returned after a two-year stretch during which he seemed to have climbed to the top of the comedy mountain, living in New York and working as a writer on big network shows. And it's where he is now, after Cosby and just before superstardom: living out of a rolling suitcase, tired and wheezy, punching up jokes.

Hannibal grew up on the west side of Chicago, in a predominantly black neighborhood called Austin. His father worked for the Union Pacific Railroad and his mother worked as a teacher's assistant. He never figured he would end up in show business, though he always enjoyed performing. "I think any black kid in Chicago, you have a group of friends who roast each other and talk shit," he explains over a pre-show burger. "It's necessary to be funny." As a student at Steinmetz College Prep, a public school in the northwest of Chicago, Hannibal played football and excelled at debate, a pastime he credits for helping feed and refine his argumentative nature. A few years ago, the Chicago Debate League named him their Alumnus of the Year. At the ceremony, his high school debate coach, Peter Bavis, remarked that Hannibal possessed the same "cool grit" during cross-examinations "that he now deploys to take on hecklers during his stand-up shows." (There's a great YouTube clip of Hannibal accepting this award from a hotel room, still harboring a grudge at the judge who voted against him in the city semifinals.)

In 2000, Hannibal enrolled at Southern Illinois University in Carbondale. He figured he would just study business or something that might result in a steady paycheck. But he started performing, first with a campus group called OOPS! Entertainment, then at local open mics and talent shows. He cracked wise about typical college concerns: dorm food, campus security, funny things rappers say, random stuff he would see on ESPN. He became so fascinated with stand-up that he left school, moving back in with his parents to see if he could hack it in Chicago as a comic. "They were iffy at first," he explains, "especially since I didn't get my degree. They weren't openly horrible to me about it. They weren't like, 'What the fuck are you doing telling these jokes?'" He chuckles to himself. "It was kinda just… silent doubt." He would try and play as many clubs as he could on any given night—a challenge, he explains, given his reliance on public transportation. With the train and bus routes near his parents' home, it was a lot more convenient to play clubs on the north side of town, which catered to predominantly white audiences.

By the mid-2000s, he was regularly visiting New York, refining his measured, disinterested style of delivery and working every open mic he could. He finally moved for good in 2009, after a brilliant set on Late Night with Jimmy Fallon caught the attention of producers at Saturday Night Live. He was hired as a writer—an unusual opportunity, given his lack of experience. As it turned out, his background in stand-up and improv didn't much prepare him for the challenge of writing for a show like SNL. "The first day," he remembers, "they said, 'Here's your office. Just write a bunch of commercial parodies.' Okay. Can somebody show me what the format for a commercial parody is?" He left after a year, during which he got just one sketch on air—about Charles Barkley's mesmerizingly bad golf swing. "I could have definitely worked harder at it," he says, "but I still think it wasn't right for me at the time." Maybe things would have been different had he been hired as a performer. "I would have been better on camera," he says. "But there wasn't time for me to really prove that."

In 2010, he released his first stand-up album, My Name Is Hannibal, and before long, he was writing for 30 Rock, where he also got some experience acting on TV. (His recurring character was an outspoken homeless guy.) While the prefab structure of 30 Rock was a better fit for the young writer, Hannibal eventually realized that writing for someone else's show simply wasn't what he wanted to be doing in his twenties. He started to catch cabin fever. "I left 30 Rock to focus on my stand-up," he explains, "but I also left to beat them to the punch of potentially firing me."

When Hannibal is enjoying himself on stage, it can feel like time is moving at half-speed. It's in the way he carefully and coolly patrols the stage, in his comfort with silence, his ear for language. During one of the night's sets, he tells a joke about how, in every city he visits, there's always a local dude who assures him, "Whatever you need, I GOT YOU." So he imagines a scavenger hunt worth of things he'd like for this guy to find—including the answer to the question of why Hannibal's incapable of living in the moment. Later, a joke about RiFF RAFF's penchant for rapping over his own vocal tracks leads to Hannibal wondering what it would be like to do comedy that way. He cues Tony, who starts playing pre-recorded jokes, including the aforementioned bit about the palm reader. Hannibal vibes out, playing his own hype-man, shouting along to the last word of every sentence.

A lot of Hannibal's jokes depend on careful delivery—his peculiar phrasing, for example, when he tells an old white couple he suspects of trying to coax him into a threeway, "I ain't down with that cuckold life"—and back-to-back sets like these offer the chance to compare the effects of subtle changes. At times, it feels like he's trying to test out a more relaxed cadence, finessing the threshold between animation and expressionlessness. Sometimes, he swaps out a reference to a city or a sports team just to see if it sounds funnier, or he changes the register of his voice when he's doing an imitation. In March, he's scheduled to do the Comedy Central roast of Justin Bieber, so he rehearses some in-progress burns for the crowd. "They say that you roast the ones you love," he starts, pretending to address the pop star, "but I don't like you at all, man. I'm just here because it's a real good opportunity for me." Then he just starts riffing, testing out kernels of jokes. He brings up our hotel, which is currently overrun by high school volleyball players. He's not sure what to do with this image, so he just starts running through his observations. "Volleyball pays for hotels?" he wonders innocently. The bit isn't coming off. He doesn't panic. He takes a few steps and says, "We need lulls in life."

Hannibal's set changes every time, as jokes come and go, but there's always a bit that arrives about three-quarters of the way through. At first it seems like a typically self-deprecating joke about dating, fear of intimacy—fairly normal stuff. What's going on, he wonders, with all these women who are suddenly interested in me? I'm still the same dude I was a few years ago. "What's your game?" he whisper-growls. "Did Bill Cosby send you?"

The applause always sounds a bit different at this point—shocked, cathartic, even a little righteous. "That situation got out of control," he offers, with a slight trace of earnestness. One time, someone shouts back, "It was your fault!" He tells her it'll be his fault, too, when he boots her from the premises.

The next morning, I ask Hannibal how he decided to structure this new Cosby bit, why it comes when it does. "I used to do it at the beginning in a harsher way," he explains. It got Cosby out of the way early, but he wanted a subtler and less predictable way to get to the question on everyone's mind. "The jokes would still work but there was less finesse to it. By moving it to the end, it seems to come from nowhere."

He explains that that situation, of wondering if a woman he met was an agent of Cosby, came from reality. "That was a real, honest feeling I had for a little while," he says. "In October, there was times when I would be like"—his voice drops to a conspiratorial low—"What is she up to? Cause it was still raw and weird. I was very paranoid about situations. That's just honest."

After the scandal broke, he turned down interviews as well as TV and movie roles he felt he was getting purely because of his newfound notoriety. He tried to stay off the internet but couldn't. He had been a comedian on the verge for a few years. He had made decisions that were about retaining control and relying on nobody but himself. Was it all going to disappear?

"It was just weird, man," he says. "It was just weird to see people talk shit about you. I saw people I thought I was cool with bashing me online. People were writing me. It was a weird thing. I had somebody from high school write me on Facebook like, 'Oh congrats—I saw you on Inside Edition.' I've been on television for eight years," he chuckles. Then he abruptly stops. "Yeah. I was not excited to be on Inside Edition. It had me a little weird about fame and all that stuff. I was feeling weird about show business in general."

After this tour wraps up in April, his next major project is Why? with Hannibal Buress, the Comedy Central series. Production will begin in May, and it will begin shooting and airing a couple months later, debuting on July 8th. He's not quite sure how to explain its premise. "It's like Weeds meets Breaking Bad meets Chelsea Lately," he says. The network, he adds, isn't going to love that description.

Later, I run the comment by Hannibal's manager, Dave Becky. He's silent for a split-second then explodes into laughter. He describes the show as a combination of stand-up, man-on-the-street excursions, and interviews taped in front of a studio audience, all driven by Hannibal's perspective on something happening in the news that week, whether it's terrorism or the maniacal genius of Russell Westbrook.

Becky is a legendary talent-spotter; his other clients include Louis C.K., Amy Poehler, and Kevin Hart. He was drawn to Hannibal's ability to bring his low-key wit to bear on any subject under the sun. The challenge, he says, has been figuring out how to harness the comedian's skill set. "In managing someone like Hannibal," Becky explains, "you kind of try to subtract things." Between writing and producing, TV and movies, touring and stand-up specials, there have to be compromises. Part of that challenge includes figuring out how to retain the subtleties at the heart of his humor—his casual crassness, eye for seemingly banal detail, and appreciation for the meta—while growing his audience. Hannibal has sold a few network sitcom treatments in the past, including an ABC series that went to pilot last year, featuring Hannibal as a fish-out-of-water, small-town cop. It wasn't greenlit, and it's hard to imagine him recalibrating his laid-back style to suit network TV's frenetic pacing.

When you're a young black comic with a cutting sense of irony, comparisons to Chris Rock or Dave Chappelle are inevitable. But Hannibal's style is a bit more inward and perverse. He's more of a witness than a critic. His humor doesn't depict a larger social world so much as it fixates on how that world occasionally intersects with the strange contours of his own life. He always maintains a quality of baffled incredulousness, which is what makes the characters he plays on TV so relatable: Broad City's Lincoln Rice, so steady and pragmatic while everyone else around him is impulsive and reckless; and the chill, skeptical sidekick he plays on the surreal meta-talk show The Eric Andre Show.

More than anyone else, his career is beginning to recall that of Louis C.K., particularly in the way his material so intimately reflects the evolving oddities of his day-to-day life. His jokes used to reference roommates and drunken all-nighters; now he talks about being able to afford Lasik ("These ain't no Kickstarter eyes"), or being on set for a movie, or his mother's desire for him to "rawdog" a girl in order to provide her with some grandchildren. It's easy to imagine Hannibal ending up like Louis, someone who always seems like he's portraying a version of himself. Perhaps Why?, as a vehicle for Hannibal's many talents, will finally provide him with the big audience he deserves.

On the second night of Hannibal's Denver run, he feels good. He's finally adjusting to the altitude, at least enough so that he can enjoy a sip of Jameson before his set. (Contrary to popular belief, he doesn't actually smoke much weed.)

He strays from the previous night's structure a bit, plugging in old jokes—there's one about an Asian dictator and Hannibal's accidental misreading of a "FREE SUN TAN" sign—and smoothing out new ones. Someone in the crowd keeps yelling out that she finds him sexy. "Women didn't say shit like that before Broad City," he shoots back. "I was just some dude talking shit in front of 600 people." Then he looks at the ceiling, thinks for a moment, and detours his set through a cluster of jokes about sex and relationships. He wonders if the altitude will affect his stamina—"I'll give you 90 seconds in this high altitude"—before conceding that he's actually "not a good first fuck." "My dick is like the Yeezus album," he offers: though he might at first seem an underwhelming lay, he merely requires patience, careful study, and maybe an open-minded spirit. "Oh shit," Hannibal says. "There's different levels to this!"

Maybe Hannibal could have arrived at this stage of his career earlier. Maybe, with so many bigger shows scheduled, he doesn't need to be here in Denver at all. Maybe there's a reason so many of his jokes draw on feelings of paranoia and insecurity, the sad humor of missed opportunities. "There's stuff I could have done earlier on to progress faster," Hannibal tells me. "Like with old TV deals that I didn't handle as well. Stuff like that. I probably should have had my own show earlier, or at least shot pilots earlier on." He trails off. "Just having fun doing stand up and not writing."

Then again: maybe he's just been busy enjoying the spoils of life on the road, being up all night and up for anything. It's brought him to the Gathering of the Juggalos and the Cleveland Cavaliers' locker room, where he got to be an NBA beat reporter for a day. When he's on tour, he goes to the movies, checks out local rappers and strip clubs. At SXSW this spring, he went on Twitter and volunteered to play drums for any band okay with allowing a comedian incapable of drumming onstage with them. (Speedy Ortiz invited him out for a song.) Earlier this year, he nearly bought the website Hipster Runoff, just to see what he could do with it. He missed the final minutes of the auction because he was at a bar, hanging out with some friends.

The only coherence to his career and its digressions is a sense of curiosity, as well as an abiding, almost stubborn faith in doing things his own way, at his own pace. It's why he no longer goes to work each day at NBC, and it's why he turned down the chance to capitalize on the Cosby bit. Right now, it means grinding through theaters, mastering the form, working harder than is probably necessary.

At around 11PM, Al Jackson is closing out his second opening set of the night with a crowd-pleasing bit about pubic hair. Hannibal's DJ finishes his quesadilla and returns to his decks. Hannibal is sitting on the couch, staring at the TV's other channel, which is a feed of the Comedy Works stage. He takes a sip of his drink and stands up, noticing himself in the mirror. "I just realized I wore the wrong fucking jacket": he cocks his head back, lets out a hearty laugh that dissolves into a raspy scribble. Then he walks on stage.

Pre-order Hannibal Buress' issue of The FADER now. It hits newsstands on May 12th.

Styling Deidre Dyer. Grooming Rachael Ghorbani.