Anytime someone asks me how I got to where I am now (wherever "a check away from homelessness and crippling depression as a Black husband and father in America" is), I give them this simple secret: You have to do the work. Nothing can replace getting your hands dirty on a project. You understand how systems work in your own language, and the more you do anything, the closer you get to mastering the craft. Money and bloodlines can get you far, but nothing trumps experience. It's a trait I saw in Hannibal Buress during the two Undock sessions we spent discussing the growing list of projects and ventures he's managing at the same damn time.

Want another simple secret? Hannibal Buress is fucking funny. He's been funny. I'm not sure of where I first saw Hannibal perform stand-up, but I do remember running through his first album, My Name is Hannibal. That was 10 years ago. Since then, I've followed him throughout his "mildly popular" (his bio's words, not mine) career, which has included numerous stints at Comedy Central (Broad City and his own series, Why? with Hannibal Buress), Adult Swim (The Eric Andre Show), and NBC (working on both Saturday Night Live and 30 Rock). He's done films (the Neighbors films, the Secret Life of Pets films, Spider-Man: HomecomingTag), been podcasting, and has been featured in two video games: Grand Theft Auto V and NBA 2K17. Hannibal's been in grind mode but has also been the catalyst for one of the more eye-opening scandals to come out of Hollywood in recent memory. I'm not surprised that, instead of trying to be more in the public eye—remember, Hannibal's the guy who paid a double five C-notes to work the red carpet for him—Hannibal would be spending more time working on the edits of his latest stand-up special, Miami Nights (which was a reference to his 2017 disorderly intoxication case, which he beat in 2018 and discusses at length during the hour) and a number of new projects and hobbies, from getting his 2K on and mastering the streaming service OBS to creating a new podcast, Splitting 10s, with his uncle, Kelven Stovall, a former casino card dealer.

Hannibal has been funny. You see it at the beginning of Miami Nights (which was released on July 3, 2020), where he shares some classic footage of his original stand-up incarnation, Hannibal Amir Natural. Being that Hannibal and his uncle are close in age (y'all know how it is when it comes to "young uncles"), they share a similar sense of humor. Based on the hands life has dealt them, they've gone down vastly different paths, but where Hannibal feeds Kelven's sense of humor, Kelven has some of the most intriguing tales based on the varying walks of life he's come in contact with. Their podcast is the most fascinating thing I've learned during quarantine, and feels like Hannibal's latest passion project, with products like Zoom allowing him to both connect with his uncle while turning passion into (potential) profit.

As quarantine evolves, it's intriguing to see how different people move. During our first conversation back in July (roughly a week after the release of Miami Nights), Hannibal was at an undisclosed location, in a studio space where I imagine he may have worked on some of the Auto-Tune bits for Miami Nights as well as recording whatever OBS-driven promo for the special, podcast demos, and other shenanigans. It's a smart investment for a landlord who is also a creative. For our follow-up, a week and some change later, Hannibal was back in his native Chicago, where he quite noticeably felt more at home and out of whatever quarantine fog he was in during conversation one. Not that the conversation suffered at all; you can just tell how new energies operate based on location during the pandemic. Our conversation spanned the work put into his new special, a car accident at a property he owns, maintaining a sense of regularity, and how he's combating his vices these days.

I spoke with Hannibal ahead of the announcement of his Let's See How This Goes drive-in theater tour—which kicks off on September 22 and touts being "masks required" while also maintaining social distancing rules.

Also Watch