It’s early November, the second night of Chicago’s inaugural 312 Comedy Festival, and the city’s own Hannibal Buress is preparing to take the stage at the Chicago Theatre in just a few hours. It’ll be the Austin native’s fourth time headlining the historic venue (his first since 2018), and he’s making himself quite at home backstage.
Backstage, after passing a series of hallways autographed by past performers, Buress gets tucked away with two laptops in a quiet dressing room.
Buress is simultaneously running through quippy lines and big beats ahead of this special performance night that will see him pulling double duty asrevered comic and a burgeoning music act. In addition to an hour of stand-up, Buress’ rapper alter ego, Eshu Tune, will also get a dedicated set, the two personas sharing equal billing on the marquee outside.
A 20-year veteran comic and actor — his most memorable stints including TV shows “The Eric Andre Show” and “Broad City” and specials like 2014’s “Live From Chicago,” and his latest film work voicing Genghis Frog in the 2023 animated “Teenage Mutant Ninja Turtles: Mutant Mayhem” — Buress switched lanes in 2022, debuting the Eshu Tune project with a self-titled, semi-self-produced hip-hop album.
The momentum has carried over into this year, most notably a slot at Riot Fest performing on the same stage as Corey Feldman and Insane Clown Posse, a setup dying for its own joke.
His tracks released so far, like “Veneers” and “Knee Brace,” have become blog fodder, praising Buress’ artistic spin that pairs his comedic voice with impressive rhyme-spitting, a combination that is largely untapped and begs the question:
Who is Hannibal Buress, really, and where’s he going with all of this?
Over the course of an eight-hour period at the theater, the Sun-Times was invited to find out.
We explored his newfound passion for music, his thoughts on the state of comedy, and how much he really loves Potbelly.
2:30 p.m.
The laughs began early at soundcheck. Buress isn’t on-site quite yet. Word is he’s still getting ready at the Robey Hotel in Wicker Park where he’s been staying the past few days. (His current home base is Los Angeles). But his presence is already felt. The seven-piece Eshu Tune live band, comprising a full horn section, keyboardist, guitarist, bassist and drummer, is running through a section of the gut-busting track, “Tallest Person at This Mexican Party.” Some of the crew and venue passersby can’t help but chuckle hearing the track on repeat — a good sign for later.
3:15 p.m.
Buress arrives and quickly scans the entire theater, jumping down from the stage to walk through the first section of aisles, seemingly to channel how the audience might feel. As he would later share in a sit-down, for him, everything centers on the live experience.
“Because I come from stand-up, which is all about the live element, I bring that into the music, too.”
It soon becomes clear that Buress likes total control over his shows. After rapidly running through verses, he gets a good look at the graphics behind him. A variety of images scroll by, including one of Buress’ face superimposed over the Chicago skyline, fitting for his local takeover as of late.
In addition to tonight’s gig and Riot Fest in September, Buress the comedian opened for Dave Chappelle at the United Center in October.
“But I got some new local material for tonight,” he promises. “I have very specific Chicago experiences … and there’s people in the crowd that went to the same high school [Steinmetz], or, at the bare minimum, know what school I’m talking about.”
3:30 p.m.
Buress is back in the dressing room on his laptops prepping for the night, but is happy to talk shop. That includes discussing his foray into music, which became a quasi-midlife reinvention that happened shortly before he turned 40 this year, and was prefaced around the time he became a first-time father in 2021. But to be fair, music is not necessarily a new hobby.
While enrolled at Southern Illinois University, alongside fellow alum and now frequent collaborator Open Mike Eagle, Buress began participating in rap battles. Even as his comedy took off, he flexed his musical muscle, performing with The Cool Kids and Chance the Rapper (Buress once directed a Chance music video). He’s also appeared in music videos for Jay-Z and Anderson Paak.
“Music happened before comedy, but not in a way where I was doing it much. I was around it, though,” Buress shares. “When I got into comedy early on, I was having positive experiences, and it was just easy to keep doing it. … I think a lot of it was partially identity, too. You know — I’m a comedian. But I appreciate that now [with music] I’m able to go into it at a high level and know that, if nobody else books me, I’m going to book me.”
It’s an MO Buress is looking to extend as a new club owner himself. He recently took over the former Knitting Factory space in New York City and will be moving to the East Coast soon to get it off the ground.
“I used to host a show there from 2009 to 2016. It was a really popular Sunday night show. And then the opportunity popped up to lease it.”
When asked if he would consider doing it in Chicago, Buress says, “I’d like to, down the line.”
As he’s talking, a blare of horns and drums rises from the stage below and Buress excuses himself to head back to the action.
4 p.m.
Watching Buress from the wings of the during the second rehearsal, it’s apparent just how much of a natural he is as a musician. It doesn’t hurt that his band is exceptional, too. As the ensemble runs through several of the songs, Buress makes cuts to the set list in real time. Most of the show is well-rehearsed, but naturally there are some improv moments, too.
The lines between comedy and music easily blur for Buress. Even during rehearsal, the dark stage, jazzy undertones and everyone dressed in black is disorienting for a few moments: Are we at a jazz club or a comedy club?
The style of music Buress chose for Eshu Tune is very intentional; rather than stick to percussive-based rap beats, he wants a full live group. As he says, “Certain instruments just hit different emotions for people. The horns in particular have a mostly triumphant connotation.”
Buress turns his focus to a stool on the stage. While some comics use it as a go-to prop, Buress is considering adding it to the performance of the cheeky track “I Lift Weights!!” — as in doing bicep curls with it. But he quickly abandons the idea.
“Do you want real weights instead?” a band member asks. “Stereotypical buff guy s - - t?”
5 p.m.
That’s the thing, says Buress, as we head back to the dressing room — the songs may seem funny on first take, but there’s messages in them.
“There’s serious topics in there. A song like ‘Veneers,’ it’s talking about teeth, but it is a serious placeholder for whatever other things people use to cover up insecurity, like alcohol, a nice car — it’s all veneers. The message and the tone can be totally different.”
Though he took a bit of a pause from stand-up while focusing on Eshu Tune, and finding post-pandemic comedy gigs to be rusty, he’s happy to be returning at a time when the field is so promising.
“The business is in a huge place right now,” he declares. “There’s a lot more people doing arenas right now, a lot more people doing big theaters and multiple nights, really because of podcasting and YouTube. It’s still a huge deal if someone plays Madison Square Garden or United Center, but there’s more people doing that than there used to be.”
“I could write really whenever I want if I just really sit back and think,” he says. “I don’t really get [writer’s] block, but if I do, I got lots of different things to look at that can be developed. Just reading a book or reading a random travel magazine.”
As we wrap up our session to give him time for a dinner break, the question of food comes up, specifically his favorite spot when returning to Chicago.
“I hit up Potbelly a lot,” he says with a huge belly laugh, though he’s dead-serious. “For real, this is not me trying to get sponsored. I’m trying to tell you the Potbelly Perks app — every two purchases they’re giving me something free.”
He opens up the app as proof. “I got 355 points to my name.”
7 p.m.
People start filtering into the theater lobby amid random chatter about the last time they saw Buress (some even remembering when he opened for Chris Rock at the same theater).
Across from the bar, merch is set up like any music star might have.
Inside the auditorium, the lights start dimming, and an announcer comes on the stage to advise there’s a “no phones policy” and to “keep heckling to zero” before the night’s two warmup acts — both local — take the stage.
The first is Marilee, who, like Buress, shows off the full breadth of her vocal chops. She offers bits about her penchant for dating old men and parlays the jokes into ad hoc blues songs that get a hearty round of applause.
Next is Leon Rogers (also part of the WGCI Morning Show crew) who has some ditties about a Make-A-Wish Foundation for adults and what he’d do if he won the lottery. Rogers hypes up the crowd for the main act, remembering the days when Buress used to open for him.
7:30 p.m.
Backstage, Sun-Times staff photographer Ashlee Rezin gets some extra time with Buress and his crew and recounts details of the talent getting stage-ready. Rummaging through his roller suitcase, Buress settles on an ensemble he bought from resale shop Crossroads in Wicker Park earlier that day. It includes a pair of tan pants, an orange mock neck shirt and a floral vest that doesn’t exactly scream “rap star.” He asks if his outfit looks OK as he rips the tags off each item and laces his new shoes.
Drummer Jesse Williams (aka Drum Smoke) quickly pops in to give a pre-show hug, and Buress starts hashing out how he was randomly gifted the clothes.
While in line at Crossroads, Buress realized his Apple Pay wasn’t working, telling the clerk to hold the items and he’d be back soon. Upon returning a few minutes later, Buress was informed that the guy who was behind him in line purchased the outfit, resulting in an incredibly awkward gifting.
“I don’t need fans buying my clothes for me,” Buress says, as the room of people surrounding him backstage cracks up.
After Williams leaves a few minutes later, bassist Izzy Johnson comes into the room and Buress tells the story yet again, eliciting more laughing fits. The bit eventually makes it into the show, and it becomes evident that Buress telling stories is really an exercise in testing out material.
By 7:45, Buress is back in show mode, furiously memorizing Eshu Tune lyrics logged into the Notes app on his computer. He notes that the audience might not realize it if he gets the lyrics wrong, but the band would notice him mumbling.
Then, he pops a pill.
“I gotta make sure the Sun-Times sees me taking my Adderall,” he tells the Sun-Times photographer. In the middle of his performance on stage later in the evening, he lets the audience know when its effect kicks in.
8 p.m.
Buress has moved to the wings of the stage. Opener Marilee gets a photo with him as he flashes a wide smile, but it quickly fades. He’s tense with anticipation and concentration, pacing 20 feet in every direction like someone in a hospital awaiting news on their family member.
Not fazed in the least by the photographer documenting his every move, Buress checks his phone, puts it in his pocket, checks it again, puts it back in his pocket, then runs upstairs to study the Notes app lyrics one more time. When he returns to the wings, Buress continues warming up — physically, this time — placing both hands on his head, stretching, then tilting his head back and pinching his temples. For a good 10 minutes, no one says a word to him or approaches him, giving him space as if they’ve done this drill before.
Buress takes one quick peek out at the audience, and as his hype man introduces him, trots out to the stage, his smile returning.
8:15 p.m.
A career reel starts playing all of Buress’ résumé high points, including various talk shows he’s been on and magazine features he’s appeared in, such as Variety’s list of “Ten Comics to Watch.” As he takes the stage, a deafening cheering erupts in the theater.
The smile on his face reads: “There’s nothing like a hometown show.”
From the get-go, he launches into timely material about the city being in turmoil and comments on the migrant population, sharing that he visited one of the protests at Amundsen Park when he was in town opening for Chappelle.
But what becomes apparent is just how much music fills in the nooks and crannies of Buress’ material, even before he morphs into Eshu Tune. He waxes on Eminem and his daughter Hailie’s lackluster podcast; he has a hilarious section about 2 Chainz asking higher powers for a set of wheels; he discusses opening a club in Mississippi with his cousin — called Playa’s Palace — in which Drake’s dad is randomly featured on an outdoor mural.
9:15 p.m.
After an hour of hilarious monologues, an abrupt transition takes place for Act II — one that clearly wasn’t rehearsed — as the curtain awkwardly lifts to unveil the Eshu Tune band. Shrugging it off, Buress shapeshifts into his rapper alter ego with ease, using many of the same spoken interludes he did at Riot Fest .
“This is the hardest song about bowling,” he says to introduce “1-3 Pocket.” For the diss track “Lamp Me,” he shares the Twitter feedback he got from a Brit who didn’t like Buress’ take on a U.K. accent and threatened violence. A few people get up to leave at this point (by now it’s nearing 10:30 p.m. after a long night of laughs).
“The brothers always start leaving when I put out the accent. But it’s OK, I like knowing the songs people leave to, it’s like focus group research,” he admits on stage.
It’s something that came up earlier during our interview, too.
“That’s the thing I’ve learned over the last year. You still have to guide folks in, lead them into wanting to know the songs. I’m still finding ways to make the music digestible to somebody new.”
