On a painfully cold Thursday morning, Hannibal Buress—his sloped shoulders packed into a drab winter coat and his round cheeks peeking over its collar—arrives at the ABC studios on State Street for a talk show appearance. The 31-year-old comedian is the featured guest on Windy City Live, but as he weaves his way through the already assembled studio audience, he goes entirely unnoticed.

Backstage in the greenroom, Buress (pronounced BUR-ess) plops down in a chair and nurses a bottle of water while looking over a list of “trending topics” handed to him by a producer. These include Derrick Rose’s multimillion-dollar endorsement deals and Justin Bieber’s recent arrest in Florida for drunken drag racing. “Maybe I’ll just take an extreme stance on everything,” he says, his eyes twinkling with mischief, before tweeting the thought to his 180,000 followers.

When he walks onstage and joins the hosts in a panel-like configuration, Buress seems amused yet apprehensive. “You have a very interesting name. Where did your mom come up with your name?” asks Ji Suk Yi, one of the show’s contributors. “My dad named me after Hannibal Barca, the Carthaginian general who attacked Rome,” Buress says. “But nobody knows about him.” (A formidable military strategist, that Hannibal famously marched 37 elephants over the Alps in the third century BC in his ultimately unsuccessful attempt to sack the city.)

Val Warner, the show’s hyper, terrier-like ringleader, follows up with, “Is he proud of you, that you’re a comedian and maybe not, like, a general? There’s no disappointment?”

Buress pulls back in apparent surprise. “No, there’s not disappointment,” he says. “I’m doing really well!”

Things go downhill from there. When the 17-minute segment finishes, Buress darts for the door. As the day goes on, the steam builds. He tweets no fewer than five times. “Really zoned in,” he writes in one post, with a photo of himself looking exasperated. “Super engaged,” goes another, with a shot of the comedian solemnly staring at the desk as the hosts chat and laugh.

By the time Buress takes the stage at the Vic Theatre in Lake View 12 hours later, the pressure cooker is ready to blow. “Man!” he roars. “I did this dumb-ass show this morning! This goofy morning television show!” He pauses, absorbing the energy of the room, and then profanely recounts for the crowd how Val Warner asked if his dad was proud of him. “What?! Who says that?!” He takes a microbeat and starts a chant: “Fuck Windy City Live! Fuck Windy City Live! Windy City Dead!”

Buress is in town to tape his upcoming Comedy Central special, Hannibal Buress Live from Chicago, an hourlong one-man show scheduled to air on March 29. In it, Buress returns to his roots as a standup comedian after a somewhat quixotic detour through network television. He moved from Chicago to New York in 2008 and, after a hellish year of gigging around the East Coast, performed a set on Late Night with Jimmy Fallon that got noticed by Seth Meyers. Meyers soon tapped Buress for one of the most prestigious jobs in the business: writing for Saturday Night Live.

The first sketch Buress wrote had Megan Fox playing a horror-movie villain who kills her victims with jazz scatting. It never aired; in fact, only one of his sketches—a bit about Charles Barkley’s golf game—was ever shown. Buress left SNL after a year for an equally covetable position as a writer for 30 Rock, Tina Fey’s hit primetime comedy. Six months later, he quit. To many of his friends, Buress’s walking away from NBC was like the ski champ Ted Ligety taking a pass on Sochi: Gold medal? Naaahh.

“With sitcom writing, you’re trying to write stories,” he reflects as he sits at a window table at Encore, a hotel restaurant in the Loop. He picks at the remains of his salmon salad, then stares down at his plate of greens as if willing it to magically transform into a cheeseburger (“My girlfriend gives me health tips like ‘Hannibal, you’re gonna die!’ ” he says later). “And with 30 Rock, you’re writing characters and stories for the entire season. It’s way more complex [than sketch work]. But I didn’t see myself as a television writer. I saw myself as a comedian working as a television writer. It was great that they gave me a shot. But I like being on camera, and I like writing for myself.”

Since leaving 30 Rock, Buress has built a national cult following on the success of The Eric Andre Show, a bizarre fever dream of a talk show that is part of the lineup on Adult Swim, a cable comedy network. He has performed live in more than 50 cities, and last winter he filmed a pilot for show that’s a send-up of reality TV: In it, Buress does odd jobs (goat farming, coaching a basketball team), then riffs on them in a standup routine. He also makes fleeting appearances as a love interest on Comedy Central’s Broad City, a sitcom about two aimless white 20-something women living in Brooklyn. (Buress lives in the trendy Brooklyn neighborhood of Williamsburg.) And he plays a cop in Neighbors, a movie starring Seth Rogen and Zac Efron that will be released next month.

His upcoming special, Buress says, consists of a lot of drinking stories. “Of me,” he says, “being drunk. Looking at my set now, that is almost the thesis of it. About being a comedian and drinking. That’s my new special. Being a comedian, drinking, and traveling. And the things that come up.”

If that sounds lazily self-referential and underdeveloped, consider this: In 2010, Buress’s apparently-about-nothing set on Mash Up, Comedy Central’s showcase of young comedians, caught the attention of Jonas Larsen, the network’s senior vice president of talent and specials. “He’s such a prolific observational storyteller with such a unique take on the world around him,” says Larsen, who gave Buress his first TV special, Animal Furnace, in 2011. “He’s like the Muhammad Ali of comedy. He makes it look so easy. He dances around you, then gets you from the side.”

As one might expect, Buress’s story about how he became a comedian barely registers as anything at all, much less a creation myth. “In grade school, I had a funny group of friends,” he recalls. “In seventh grade, I went to [the Chicago magnet school] Whitney Young. And that’s when I started cutting up. Then I went to high school at Steinmetz [a public school on the Northwest Side].”

Which prompts Buress to ponder this somewhat backward-moving chapter of his life. “My group of friends at Steinmetz were real fuckups. They were real fuckups. They were cutting class, smoking weed, stealing, flipping the desk—a lot of crazy stuff. My last year of high school, I was on the debate team. Even while being a fuckup and doing goofy shit, I was still somewhat focused on going to college. I graduated with a 1.9 GPA.”

He pauses. “I think it’s also because I have ADD [attention deficit disorder] that was undiagnosed then. I think that’s all it was.”

The idea, like many of his observations, makes him laugh. He leans back, his shoulders hiked up and his head pitched toward the ceiling, and lets out a sardonic cackle that sounds like the evil laughter of a cartoon villain.

Whereas some comedians draw on dysfunction or extremism for their material, Buress’s obsession with life’s mundane aspects may be rooted in his rather undramatic upbringing. The youngest of three, he was raised on a stable, middle-class block in otherwise troubled Austin, the Far West Side neighborhood bordering Oak Park. His father, John, worked for Union Pacific Railroad—although Buress declines to remember exactly what his dad did for a living. (“I don’t know; I will never know,” he says, when pressed. “He worked hard for his family and now he’s retired.”) His mother, Margaret, was a teacher at St. Paul Lutheran School in Austin. “I skipped kindergarten because I was reading at a pretty high level,” he says. “That’s a weird and cocky thing to say, but I was real sharp and I knew that early on.”

However, Buress allows that he probably wasn’t ready to make the transition from a small neighborhood elementary school to Whitney Young, one of the city’s most rigorous and diverse academic centers. He flunked out after eighth grade. “I think it was an environment shock,” he says. “It wasn’t about the people. It was about changing classes.” Moving around the huge building from English to math to gym to science might have been too much freedom, he says, and he took advantage of it by skipping class.

In 2002, when he was a sophomore at Southern Illinois University, Buress made his first standup appearance at an open-mike night in the basement of the school’s student center. “I told a joke about how I was upset that the national spelling bee was on ESPN,” he says. “I remember my legs were shaking when I got offstage. After that I was really zoned in. The most focused I’ve [ever] been.” Buress says he mined his everyday life: complaining about living in the dorms, ridiculing students who worked as campus security guards, detailing the awfulness of cafeteria food, mocking rap lyrics. “I had a joke about how Nelly says he’s a sucker for cornrows and manicured toes,” he says. “And I was like, ‘No women get their toes pedicured!’ It was all still pretty easy stuff. I was 19, so I wasn’t really drawing from within yet. I didn’t have much life experience to talk from.”

He started doing comedy anywhere he could, once in a while making the five-hour journey from Carbondale to Chicago and finagling his way into booked showcases. One of the first comedy nights he cracked was at the dingy but popular bar Cherry Red in Lake View. “I was a brand-new comic, and I walked up and asked if I could get on the show,” he recalls. “And the guy working the door was like, ‘Nah, it’s a booked show. The lineup is set.’ I was like, ‘Dude! I’ll do three minutes! Let me do one minute!’ I was so fucking annoying. So needy.” But the persistence paid off: The club booked him several times, even though he was underage.

Buress stayed at SIU for four years but failed to graduate. “After I started doing standup, I couldn’t really focus on class,” he says.

So he moved back to Chicago, where, on any given night, you might find him trekking all the way from Jokes and Notes in Bronzeville to the Lyons Den in North Center to a late-night open mike at the Heartland Cafe in Rogers Park. “He always had this sort of I-don’t-give-a-fuck attitude,” says T.J. Miller, a standup comedian who met Buress in 2003. “I remember one time he said, ‘I’ve been going up and bombing everywhere. It’s great. I love it. It’s hilarious.’ He’s absolutely fearless in that respect.”

Some comedians work out their material at the desk; Buress says he does it onstage. “You have to figure out how to say something—what words to hit, where to pause, where to elaborate, where to cut out parts,” he says.

By the time Buress first performed at the Lincoln Lodge in 2004, the comedian had built a sizable following in Chicago. “The first time we booked him, Hannibal blew the doors off the joint. And instantly we started booking him in heavy rotation,” says Mark Geary, the producer. “I’ve been producing comedy for 15 years and I’ve seen hundreds of comedians, and most don’t come out the box that good.”

When Buress left for New York in 2008, he had amassed a solid arsenal of polished bits, including one about kicking pigeons: “I really want to kick a pigeon. They walk around like they untouchable. I’m like, ‘You not untouchable. I’m going to kick the hell out of you.’ But if I kick a pigeon, some lady is going to tell her husband that she saw a guy kicking pigeons in broad daylight. Her husband is going to tell his boss, who knows someone at the paper, and then it will say on the front page of the Times, ‘Black Dudes Are Kicking Pigeons.’ ”

Bert Haas, executive vice president of Zanies, the famous standup comedy club in Old Town where Buress eventually earned a slot in the rotation, says the comedian’s hopscotching résumé of late smacks of pure strategy: “I think Hannibal has an incredible sense of business. He went to SNL to write sketches, jumped to 30 Rock to learn how to write characters, and now he’s writing for his own show. Very savvy.”

Buress’s style today is rambling and unpredictable and can swing from cerebral mumblings to loud rants. Some of his friends in the industry liken him to British comics because of his willingness to walk a joke down a path even when it becomes surreal or kind of weird. They also note that Buress’s laid-back delivery is meticulously constructed and rehearsed. “Hannibal knows the places people will laugh,” Geary says. “He’s got this mix where he’s presenting what appears to be more of a freewheeling style of comedy, but he’s actually delivering something that’s very polished.”

The comedian’s best-known joke is probably his bit about pickle juice: “I have a situation in my apartment right now. I have a surplus of pickle juice in my apartment. . . . I don’t like throwing out the pickle juice. It just feels wasteful. So lately I’ve been dipping my fingers into the pickle juice and flick it”—here he mimes a full five-finger flicking motion—“on my sandwiches for flavor.” Buress says that to this day fans will e-mail him whenever pickles are mentioned in the news. “It’s fun to have jokes like that,” he says. “I’ve seen great comedians who have crushed it, destroyed harder than I ever have, but if you asked me [to remember] one of their jokes, I couldn’t tell you.”

Wondering out loud about his place in the pantheon of comedians, Buress ventures this: “For me, I just want to be very comical. It’s just different ways to make people laugh. So I like to have goofy physical jokes, something that’s real dumb and dirty, or just something about eating, or something political. I want to be able to do a little bit of everything.”

Then he finds a metaphor: “Like basketball. There’s a lot of different ways to get to the basket. Some people are 3-point specialists, where they just spot-up at the line. Some people are in the post: They’re big, they stay by the basket, they get rebounds, they put those back. Some people have a midrange jump shot. I want to be able to score in as many ways as possible.”

These days, Buress says, he’s fashioning his career after comedians-turned-entertainment-moguls such as Seth Rogen and Judd Apatow. And although he doesn’t avoid talking about himself as a black comedian, Buress doesn’t focus much on race in his jokes, nor does he seem to think of blackness as a defining trope. “I’ve been compared to a lot of people, white and black,” he says. “I just do comedy. I tell stories and I talk about stuff I think is funny. And I’m black. I’m a black man. That’s how I contextualize it.”

Buress worked the black comedy club circuit early in his career but acknowledges that his audiences since have been mostly white. However, he says that lately more African Americans have been coming to his shows: “I joke a lot saying that I’m doing a reverse crossover.”

Buress says he’d eventually like to have his own TV series and a production house while continuing to act and do standup. “The ultimate thing is creating your own stuff and making projects for yourself,” he says. “That’s what Seth Rogen does. He’s writing and producing a lot of the movies that he’s the lead in.”

Back at the Vic, Buress has the crowd wrapped around his finger as he jumps from stories about peeing himself at a dance club (the result of taking Ecstasy) to getting suckered into a Mexican time-share racket. He starts a story about teaching his niece and nephew how to gamble but is momentarily derailed trying to remember their ages. He begins to mutter into the mike but cuts himself off: “Nope. I am not going to say that dumb shit I was about to, because I do not have the IQ of a Windy City Live host!” The people in the audience howl. They are with him.

Buress runs with it—and his diatribe against the morning talk show is in full swing again. “This is a weird beef I’m starting right here,” he says, laughing. Then, as though reading a newspaper headline out loud at the breakfast table, he booms, “Hannibal Rails Against Morning TV Show!” He looks up for effect. “Doesn’t Hannibal have better shit to do?”