We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

Hannibal Buress has quietly been a staple of Chicago’s independent hip-hop scene for the past 20 years.

At this point, he’s is a towering figure in standup, who’s racked up many of comedy’s biggest resume lines: an SNL stint, a beloved sitcom character (Lincoln, Ilana Glazer’s doofy fuckbuddy on Broad City), an Adult Swim swim hit (his laconic presence helped make The Eric Andre Show), helping take down a sexual predator (Bill Cosby), five standup specials, and joining the Marvel Cinematic Universe.

Throughout it all, Buress has been writing verses and starring in videos for his college buddy Open Mike Eagle, as well as Jean Grae and Quelle Chris, Serengeti, BJ The Chicago Kid, and Chance The Rapper. A music enthusiast, he’s interviewed everyone from Mitski to Lizzo on his podcast The Handsome Rambler, where he and guests freestyle and mess around on theremins and synthesizers while they chat. He’s toured with his DJ project, DJ Burgerfeet. He hired Flying Lotus to be the house DJ on his short-lived Comedy Central show Why? With Hannibal Buress. His comedy has skewered hip-hop, with parody songs like “Gibberish Rap” and indie rock (see his “Move to Philly” monologue or the Ariel Pink episode of The Eric Andre Show). He’s shared the stage with, and seems to know, just about everybody in hip-hop.

Buress is now attempting to make the tricky transition from music-adjacent comedian to rapper. He released his first self-titled EP under the moniker Eshu Tune (named for a trickster god from Nigerian mythology) in May, and last week, dropped a new single “Knee Brace.” Standup and acting, which Buress has repeatedly said he’s bored of and flat-out “doesn’t like” respectively, are on hold as he tours his music — popping out to play his tracks at friends like Danny Brown, the Roots and Robert Glasper’s shows, and seemingly DIY booking his own gigs around the country.

The lines between musical comics, comics with music side-projects, musicians who do comedy, and musicians who are just funny, are flimsy and overly-fussy. Especially in hip-hop, where there are traditions of comedy rap from Fresh Prince to Odd Future, full-fledged crossover successes like Childish Gambino, and comics guesting or being sampled on songs. Buress has arguably been and done all of the above. But while there’s an ongoing boom in musical comedy (Bo Burnham, Whitmer Thomas, Zack Fox, Cat Cohen, James Acaster, Dylan Adler, Jaboukie Young-White), Eshu Tune is firmly planted in the music world.

Eshu Tune songs are funny, but Buress can rap. This has been clear since his feature on Open Mike Eagle’s “Doug Stamper” in 2014, which showed that his nerdy offbeat persona and nonchalant delivery works as well on a rap verse as it does playing a dentist. Buress always plays himself and he’s not putting on a front in his rap. The main refrain of “Knee Brace” goes: “Hit it from the back with my knee brace on/ The velcro part keep catching the thong.” He later adds over a clean, mid-tempo club beat, “Shawty acting all bumfuzzled/ Everything is cattywumpus.” Other songs lean into silly, meta bits about veneers, bowling, and how to sample.

Eshu Tune’s funniest tracks, though, are the more serious ones, which transpose his off-kilter humor onto earnest topics like being a new parent. On “Kept About 3,” he raps through an anxiety spiral about accidentally losing his baby in a bet. “Donde Esta” and “Back In The City” are classic origin story songs, where he reflects on Cosby, his issues with alcohol and gambling, and building up the confidence to finally do music.

While Buress can’t escape the shadow of his own name or wildly successful comedy career, he’s admirably committed to starting over as a rapper. If that career suggests anything, it’s that he’s smart, funny and a good enough performer to do his thing in any medium. Buress chatted with us about getting bored with comedy and revisited some of the many musical highlights of his career.

Eshu Tune and “Knee Brace” (2022)

Why did you create Eshu Tune, and what made you want it to be a standalone project from your comedy?

HANNIBAL BURESS: Once everything was shut down in 2020, it allowed me to really focus on it. ‘Cause everything else was weird. Standup gigs were weird. The TV and movies that were active at the time, they were weird. You had to have a wristband, take tests every day. You stay in this resort, the crew stays in this resort. I realized, “Oh, I don’t like acting that much. I don’t even like money that much. So I’m gonna just go to Hawaii and go to the studio and do this.”

I always wanted to do music. I dabbled in it and recorded. On my old podcast, The Handsome Rambler, we’d veer off and freestyle a lot. We’d also started making jingles for our advertisers, ’cause I hated just doing regular ad reads. So we would kind of over-deliver and produce our own songs, instead of reading the copy. That’s actually where my school of writing hooks comes from, writing ad jingles every week.

Once stuff started to open up, that allowed me to test the songs and see how people respond to stuff. That forced me to start structuring things better, learn how to select songs for the set, curate, see what people respond to. Just in the last week, I feel like I’ve got my live set down.

Is it interesting to be an amateur again? Going from the top of your game, being able to do virtually whatever you want, to playing small rooms, all this 101 stuff?

BURESS: Yeah, it’s really fun. I do open mics, I perform for, like, six people sometimes. But I just have that feeling of momentum, of: Who knows what’s about to happen. I haven’t had that in a long time. ‘Cause I really don’t know. There’s a lot of cool stuff happening. Everytime I pop out somewhere, people say “Oh, I didn’t even know you rapped.” And I say, “That’s why I’m here, to let people know that I’m rapping.” It’s been cool ‘cause I’m not operating on autopilot, and I was in that space with standup. With standup, I was at a place where it was more of a show-me-the-money type mentality [Laughs]. ‘Cause I’ve been doing it since I was 19. It wasn’t really fun anymore. Even when stuff opened up, I just didn’t feel like taking many gigs even though they were out there. I’m doing one in December, but that’s it. Now I just look at standup as a way to convert people to the music. It’s my only comedy club of the entire year. I’m really just planting a lot of seeds for touring next year and festivals and releases.

I’m also producing. I produced the first half of the Eshu Tune EP. That gets kind of lost a little bit just because of the whole system — that gets lost a lot anyways with producers — but also because I’m the face and shifting from standup, people don’t even realize, “Oh, he made beats on this shit.” I’m learning keys, I’m learning other stuff that makes the live stuff better too. ‘Cause beyond anything else I want the live show to be dope.

Some of your songs could easily be standup pieces, like “Knee Brace.” But others are a lot more serious. Is Eshu Tune about making space to be more earnest or serious?

BURESS: It’s just a way to compartmentalize. Once I found a name, it was just a way to go: This is this, and this is that, and this is what we do over here. Maybe they work together sometimes. Even in the silly songs, being able to get some messages in there, or different frustrations. You know “Knee Brace” is a little bit about people giving me pushback within this space, and not getting support from a couple people.

Is there an artistic difference to you between comedy music and funny songs?

BURESS: There’s just a difference in flow and performance. When I’m doing comedy live, it’s really tough for me to get into flow-state. Because processes are kinda delicate with the audience. If somebody yells out, you know, it disrupts a story, especially if it’s a longer piece. Especially if I’m in a small venue, and somebody is filming me, it’s super disruptive. I stop the whole shit. Like, please stop. When I’m doing music, I don’t care. If you’re filming, as long as they’re not blocking my camera guy, I can still lock in and do my shit. For the music shows, the conversation is already set. I’m doing these songs, I got a set list. I might veer off, the banter might be something, but it’s set. Whereas, in comedy, you’ve got stuff planned but the audience can shift it. Over time I started developing more set pieces that had more predictability like “Gibberish Rap” or a DJ with sound cues or something on a screen, stuff I can depend on, that works no matter what, that helps people see what’s in my brain a little bit better.

Winning A College Rap Battle Against Open Mike Eagle At Southern Illinois University (2002-2004)

You were in a rap scene when you were in undergrad, at Southern Illinois University, which is where you met Open Mike Eagle. You once beat him in a freestyle battle. How did that go down? Back then, were you ever considering the music route instead of comedy?

BURESS: I don’t think I considered it then, seriously, because it didn’t seem as feasible or accessible as comedy. You know, 2002, rap was very mainstream, very record deals-oriented. There were independent scenes, but the alternative or independent hip-hop game was definitely a grind. You know, that was when Nelly popped, that was when Ludacris was popping.

Open Mike wasn’t even doing songs yet. At that time, he was just a really dope freestyle rapper and battle rapper. But yes, I did beat him once in a freestyle battle … somehow [LaughsLaughs]. I knew battle rapping was all about the reaction from the crowd. So I took that opportunity to get up there and be funny. And I was the better overall rapper at the time, or in that moment, that crowd thought so.

“Gibberish Rap” (2012)

“Gibberish Rap” was one the first times music really showed up in your set. You’d perform it live like, five times in a row and bring ballerinas out to dance to it. It became kind of a cornerstone of your live show.

BURESS: Yeah, that was when Tony [Trimm, DJ and co-host of The Handsome Rambler] had his mixtape Charcuteries And Champagne. I hosted it and he was playing different beats and I was freestyling, talking. And I was like “I like that beat a lot.” It just had a lot of momentum to it. Even now, these days, that’s the kind of beat I connect to you. Just driving, that pace, a lot of stuff I really like is around that BPM, which I’m guessing is in the 140s.

Do you feel like that song was the blueprint for your music now?

BURESS: Well, what happened was — ’cause there’s other stuff on there, some other freestyles on that project. But that was the one where I was like “Oh, that’s something.” Even though… [Laughs] I should’ve finished the words, but I just felt like my energy on there was right. At the time, creatively, I think I felt really fearless or something. Because we just did it and I was really hyped to put it on SoundCloud, send it around, media started covering it.

Yeah, and then when it came to doing it live, I wanted to have dancers … because I was confident in it, but I wasn’t fully confident in it yet [Laughs] So to protect my own brain and the song a little bit, at first I was like, let’s have some typical hip-hop dancers and whatnot. But then I saw this video of my friend Jabari [Johnson], who used to throw these parties, R&B Only, which was this really dope touring/concert series. And he had these ballerinas, and they were dancing to “Bandz A Make Her Dance” by [Juicy J]. The ballerinas were probably inspired by Kanye. I just liked seeing ballet juxtaposed with that type of music, so I reached out and I asked about those dancers, so he linked me with them, and they came by and we did it for the first time at the Front Bar at the Knitting Factory.

How’d it go over?

BURESS: I mean it was a spectacle. People like activity for their brain, you know? If you came to see me, you’re not expecting ballerinas to pop out, especially at the front bar of the free comedy show. I mean, I’d like to hear from people who saw it [Laughs].

I actually saw you do it when I was in college. It was really unexpected and really funny.

BURESS: Yeah, sometimes it didn’t go over. Which I mention on “Back On The City.” That was the last song I recorded and that’s me … I realized that I did that kind of joke song because I didn’t feel like I could fully do music yet. That track is kind of me expressing that.

“Get Yourself Together, Man. Move To Philly…” Monologue On The Eric Andre Show (2012)

Another iconic music-related bit of yours is the “get yourself together, move to Philly” monologue from The Eric Andre Show. Where did that come from? Were you surprised when it blew up?

BURESS: Yeah … no, I didn’t realize or expect it. A ton of stuff has gotten repurposed from The Eric Andre Show after the fact. Because how the internet functions is so different. I’m from the era of TV where, there’s TV, and then it’s on TV, like that was it. So that started happening a couple years later. It’s always wild to see. That and the “Who killed Hannibal.” That was weird because it’s like, I’d just be on the internet and randomly see myself getting shot. Just like, “Oh … this is not what I thought this would be.” But yeah, “Move to Philly…” that’s what we introduced our Philly show with. You know, move to Philly, buy a loft. It kicked off the Philly show in a dope way.

I know you interviewed Animal Collective once. Did you guys discuss it?

BURESS: I did interview Animal Collective at MoogFest. You know, I wasn’t as prepared for that one [Laughs] as I should have been. Some of those interviews, where I didn’t need the preparation because I had a relationship with them, like Flying Lotus or Open Mike. But that one … we were kinda rippin’ and runnin’. That one was very, uh, loose.

Directing Chance The Rapper’s “NaNa” Music Video (2013)

How did you meet Chance and how did that end up happening? It’s kind of a parody video, in the same vein as “Gibberish Rap.”

BURESS: So that came through Jash, which was an old YouTube channel … I think it was run by Sarah Silverman and Reggie Watts and some other people. Jensen Karp put that video together. He reached out and said, “Do you wanna direct a video for Chance?” It was between “NaNa” and “Favorite Song.” That video was another time where uh … I put a higher premium on preparation now, if I don’t know how to do something. I didn’t know about treatments, none of that stuff. We got $5,000 and I was just like “Let’s wing it through the streets of LA.” I was into costumes at the time because I was doing costumes at the time for “Gibberish Rap.” So I was like, let’s hit Hollywood Boulevard and dance with them, okay okay, let’s hop on a double decker bus and shoot on this bus. Then we passed the Laugh Factory, and I was like, I think I can get us in there. We just knocked on the door and they let us and we just moved around like that. It was fun.

Sounds like you’ve become more of a perfectionist over the years.

BURESS: I still love improv and winging it. But you can do that within a dope structure, with a dope plan. You know, I haven’t gotten any offers to direct since then. I’m using this, this is me saying I want to direct videos, I want to get back into that, now that I got some other skills and all that.

Interviewing Mitski on The Handsome Rambler (2017)

How did Mitski end up on your podcast? Were you a fan?

BURESS: So no, I didn’t know her music at the time. But I’d seen a clip of an interview with her and thought she was really funny and interesting and just thought she’d be a good get. So I just reached out cold. Sometimes I booked off stuff like that. We had a great talk. It flowed really nicely, super chill and casual. It’s been crazy watching, she really blew up over the past few years. You know, that episode is one of the ones that still gets a lot of hits.

Sitting In On Drums With Speedy Ortiz At SXSW (2015)

BURESS: Yeah that was … you know, I wanted to play drums as a kid. But yeah, it’s tough to jump in and drum live with people. Especially when you don’t even drum privately.

You look like you’re having an amazing time.

BURESS: I mean, I might have been able to do alright if I had listened to some songs before. Obviously there’s levels to it, drumming, but a lot of times you can keep it kind of simple and hold it together is what I’m learning. Everything don’t gotta be [Mimes complex jazz drumming]. Sometimes it’s just “dum dum bop” and holding that steady. But I didn’t know that at the time. Now I got a kit at the crib so I can hold some steady shit for a little bit, just basic “kick kick smash.”

The next year, I did it again. I tweeted out that I wanted to play keys and I stopped by and played with some band, while I was in space, on some … stuff.

Playing Himself In Jay-Z’s “Moonlight” Music Video (2017)

How did you get cast in that? What did you think of your role, as the guy calling Jerrod Carmichael out for being a sell-out?

BURESS: They reached out about that. I don’t know nothing beyond that. Initially, I was supposed to play Ross actually, I was supposed to be in the Friends cast. But then I got changed into the hater [Laughs]. Recently an editor put together all my music video cameos … to put them together that was cool to see. And yeah, that was wild, being in a Jay-Z video. I’ve been listening to him since Reasonable Doubt, which I think was in ‘96, when I was in junior high. To have that progress that way, that was really wild. I watched my cameo in that for the first time in the past couple weeks. It’s wild.

How did you feel about getting switched from Ross to yourself?

BURESS: I didn’t mind, I like playing myself, or a version of myself anyway. Because then it just means that I ain’t gotta … I can just chill. That’s an honor [Laughs]. For someone to be like “Just do what you do.” You ain’t gotta stretch much or like, [Putting on voice] “This is the backstory of this character, da da da da.” Just talk how you talk, you can make up some stuff. Do ya thing.

Imitating MF Doom At Adult Swim Fest (2019)

https://twitter.com/_mfdream/status/1195594066932617217

Whose idea was that? What was it like to be MF Doom for a minute?

BURESS: That was Lotus’ idea. I just went with it. I wish I knew that song a little better so my rap hands would’ve been on point. It was one of those where … It was cool to do in the moment. You hear the crowd, but you don’t feel the impact of it ’til after, when you see all the stuff about it, the coverage, people’s messages. The fact that people still kind of talk about it, it’s one of those, where you get the feel of it, and how people felt about it in that moment later. I like that type of stuff, obviously. So it was an honor to be the last Doomposter.

Performing as Eshu Tune with Danny Brown, The Roots, Robert Glasper (2021-2022)

You’ve performed with a lot of musical icons in the last year. Danny Brown in Detroit, the Roots at Pitchfork Fest, Robert Glasper at Blue Note. Does doing stuff feel different now being on stage as a fellow musician, not a hype guy or a comedian or a friend? Was there any recent performance that’s really memorable?

BURESS: It’s been really … all of them were memorable, in different ways. Danny Brown at Detroit Thanksgiving, that was sick because it was November 2021, so that was after being in quarantine for a while, I wasn’t super active at that point. Actually, that was the first time I popped out somewhere as a surprise guest. Danny liked “Veneers,” and initially I was gonna do more, but then I saw how the crowd was, and I was like, “You know, I’m just gonna do ‘Veneers.’” Cause I didn’t have a ton of other stuff that bopped then. Danny hyped me on it and helped bring the energy. That was cool to have that energy and just seeing that the stuff worked live. So that one was really special, because it was the boost to go into 2022.

Recently with Glasper, that was really cool because I just saw he was in town. I was doing the Mirage, I did it Monday or Tuesday and ended up just staying in New York so I hit up Glasper and asked if I could pop out and he said yeah. Doing those tracks now being more confident, especially in a jazz club where people really are listening, seeing the lines really hit with them. Initially I was kinda worried about doing songs that are goofy and songs that are sentimental. and I was like “Oh, can I do these different types of songs?” But I’ve just realized I gotta do what I enjoy and trust in that.