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For as much as we have a collective love-hate relationship with social media, one of the undeniable benefits of this era is how it has empowered truly creative people on all corners of the Internet. Comedians seem to have benefited the most from the short form and far reach of platforms like Vine and Twitter (besides white supremacists, I guess?), and as our outlook on society becomes increasingly bleak, we turn to humor for transgression, release, and catharsis. Comics like Rob Delaney, Zack Fox, Megan Amram, and (Bentzen Ball alum!) Aparna Nancherla have mastered comedy in the digital age, and all have become darlings of the “always online” set.

While there’s no objective way to measure this, there is one name that stands out: Jaboukie Young-White, self-described “Short King”, and arguably, the funniest person on Twitter. Jaboukie’s rise has been meteoric and well-documented elsewhere – but suffice to say, his rising digital notoriety led to writing for the Netflix show Big Mouth and an on-air gig as a correspondent on The Daily Show. Depending on who you ask, he might even be entering mononym territory – rarified air that Millennials usually reserve for women from Houston like Beyoncé and Jia. We had a chance to chat with Jaboukie over the phone last week in anticipation of his return to BYT’s Bentzen Ball.

Jaboukie Young-White is performing at Washington DC’s Lincoln Theatre on Friday October 25 as part of The Bentzen Ball Comedy Festival Presents: The New Negroes. Tickets are available here

Brightest Young Things: I saw you perform at Bentzen Ball 2018 and you were a total fucking highlight. I’m really glad to see how things have taken off for you. How have the last few years been since you “sounded so white” that Megabus, of all companies, bought you a roundtrip plane ticket to North Carolina?

Jaboukie Young-White: [Big laugh] Wow, that’s a throwback. That’s a throwback! You know, it’s not something that I really think back on that often. I still haven’t taken stock of everything that has transpired in the last few years. There are moments where I stop and realize everything is crazy, but I don’t think the full weight of it has settled in and I don’t think it will for a while. Honestly, one thing I have noticed is that shit started happening to me before my brain was fully developed. [Laughs] I don’t think I had the depth to fully understand what was going on at that time. It’s funny to look back on things like that. But yeah, it’s really good. I can’t complain at all.

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BYT: A few bands and artists I’ve spoken to over the years have mentioned how grateful they were to have encountered fame at a later point in their life, because they didn’t know how they would have handled it in their early twenties.

Do you have any rituals for self care, or staying sane and grounded? So much of your humor is in that relatability – of being in that state of flux that is your twenties. How are you managing?

Young-White: [Pauses] Um, Zoloft? [Laughs] That’s dope. But other than that, I’m in therapy, I make sure I exercise. Honestly what throws me off is having a really erratic schedule, which is literally in the job description of what I do. Little things that keep me grounded – when I was touring in college and doing shows on the road, I told myself that at least once this week I had to work out or go see a museum. Just like, make time for myself. I find that what I’m doing doesn’t even matter; I do a lot of hippie-dippie holistic shit that very well could not even work. But I think the fact that I’m taking time to do something for myself – that in and of itself is enough. The specifics don’t really matter to me, I just need to take time to replenish myself and put energy into myself. My body can’t solely be a tool or vessel to make things. Trying to fill myself back up – whatever way that is – is how I stay grounded.

BYT: Do you have a preferred workout you like to do? Are you a spin person, do you go for a run, or jump rope or whatever? Or do you mix it up?

Young-White: It has to be high intensity training. I have to feel like I’m almost going to die. Waking up early in the morning and working out to the point that you think “I might not going to make it out of this” – you get me? Once you’ve conquered that you feel like you’ve already accomplished something for the day. I feel less pressure.

BYT: That’s a good perspective. And regarding art museums, what are your favorite kinds of art? Are you into contemporary pieces or are you more of a fan of the Renaissance era and Dutch Masters?

Young-White: Honestly, I understand the importance of it and it’s so great, but Dutch [Masters], Renaissance shit – I feel nothing at all. [Laughs] I mostly go to modern and contemporary exhibits; I love sculpture, that’s really meaningful to me. Anything that is three-dimensional or dealing with mixed media. I love video installations and light installations are the gayest of all visual arts. [Laughs] I think I’m looking to experience an image I haven’t seen or experienced before, or something that captures something in me that I forgot. It either has to be new or pull up something in me that I didn’t remember I felt previously.

BYT: That totally makes sense and explains why you’re also a fellow fan of Yeezus.

Young-White: Yes! Exactly. [Laughs] Exactly.

BYT: I can see the gravitational pull towards a piece of art that’s either transformative of something that came before it, or transgressive. 

Young-White: Yes! Absolutely – transformative or transgressive.

BYT: I know you’re a Chicago native and have been on the East coast for a couple of years, with a short period in LA. How has that shift been? Do you love New York still?

Young-White: Yeah, I lived in LA for almost a year to the day – three hundred and sixty-something days.

But yeah, when I first moved to New York I was like “fuck Chicago! I’m done with Chicago.” I grew up in Harvey, which is a suburb of Chicago, and then I went to school downtown at DePaul. And even Harvey was extremely segregated but downtown was as well. I remember this one time I was on the train going towards the DePaul Campus going to the Unique Thrift Store on Archer and 35th, like off the Orange Line and there’s this stop where you have to transfer to the Orange Line on the Red Line. Wait – you know Chicago, do you?

BYT: Yeah, I moved to D.C. from Chicago. I used to live right next to the Hancock Building on Mies van der Rohe and Chestnut.

Young-White: Ohhhh! Ok! So you know! [Laughs] The whole choreographed move of all the white people on the train getting up immediately after Jackson (Station).

BYT: YEP. [Laughs]

Young-White: I just felt like I couldn’t do it anymore, it was so insane. Everyone acts like it’s normal – it’s not normal! [Laughs] And I had always wanted to live in New York growing up. But honestly at this point I’ve taken off the rose-colored glasses. When I first moved to New York I lived in a co-op and my rent was so, so cheap. Essentially I would do a couple freelance gigs to make rent and the rest of the month I would do stand-up. I would wake up at 3 p.m. every day and manically Tweet. When I first moved to New York I was living like a trust fund kid without a trust fund, essentially. It seemed so magical and full of opportunity and gorgeous and beautiful. Now that I’m back and actually working. [Sigh] You never know, I could see myself living in Chicago again.

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BYT: I moved to Chicago in September of 2012 for a relationship that soon went to hell. I’d never been to the Midwest before, I’m from the Dominican Republic and Afro-Caribbean, and then next thing you know it’s cold and lonely as fuck and I’m living in the Viagra Triangle. So, yeah. I made it seven months to the day. I was not ready for that. 

Young-White: Oh. My. God. [Laughs]

BYT: And a lot of my friends on the North Side were nice Jewish kids who went to New Trier or Wash U (Washington University in St. Louis) and they were lovely. But it was weird to me that I spent months without seeing another black person who wasn’t working a shift somewhere, you know?

Young-White: [Emphatically] Yes, yes, yes! Honestly, I had the exact opposite of that experience when I went to Atlanta for the first time. I mean, oh my god – the Mayor is black! The rich people are black, the poor people are black, the homeless people are black, everyone was black. It was so wild to see just black people doing things. Chicago feels like such a strange case.

BYT: It’s funny because D.C. is changing – and gentrifying – rapidly, but everywhere you go you’ll see people from all backgrounds hanging out in the same space. Generally speaking it’s a really wonderful mix. But I’m always curious about that transition from one physical space to another as a minority. 

Young-White: Mmhmm. For me, moving to New York was really surreal also, it was my first time being on the street and seeing someone who looked exactly like me. That’s not someone who looks like my cousins or uncles from Jamaica – I was just around too many Dominicans and Puerto Ricans. [Laughs] For the first time in my life I felt invisible, which was great. I loved that feeling of not feeling necessarily out of place or in place but just moving through space. It didn’t feel as charged as it did in Chicago. Of course, there’s an element of being an outsider moving into New York and thinking “oh it’s so pretty and magical here” and not realizing the destruction that I was causing. But beyond that it was epic. [Laughs]

BYT: I think that’s the conflict. You step into a world where you’re making a certain degree of money and you’re also gentrifying even if you don’t look like a gentrifier, and you’re maybe a minority along other lines. But then you think “Hey that’s a really affordable apartment and there’s a Whole Foods a few blocks away.” It’s certainly a dilemma I’ve faced. 

Young-White: When I moved back to New York that co-op I used to live in had an open unit. And while I really liked living there, it would be so fucked up for me to be writing and working in TV and living in a government mandated single-occupancy situation. Yeah, I didn’t think that was cool. [Phone rings] Wait – can you stay on the phone for a second?

BYT: Sure. [About a minute goes by]

Young-White: Damn, I ordered pizza from Postmates or Grubhub or whatever, and I think he got lost. But he’s here now – we’re good.

BYT: Oh nice. What kind of pizza did you order?

Young-White: Oh, I got cheese, mushrooms, and red onions. I didn’t want to do too much.

BYT: Interesting combination. What are your thoughts on pineapple on pizza? I feel like you’ll have strong opinions on this as a young Millennial. 

Young-White: I absolutely love it. But I had a little too much sugary stuff today so I wasn’t in the mood for a sweet pizza today, I wanted something savory. I wanted something with a [makes clicking sound twice], you know what I mean? Pineapple wasn’t right at this time, but I love it.

BYT: Yeah, fair enough, I get wanting to do something different. 

So, back to talking about gentrification – where do you live now?

Young-White: [Laughs] I live in Bushwick now. Which is not necessarily better! But it’s not like I’m poaching an apartment up from someone who really truly needs it. And also, my brother lives with me now and he goes to St. John’s. If I lived by work it would take him three hours to get to school. And honestly I prefer Brooklyn – I really don’t like Manhattan.

BYT: How has the transition gone from being a stand up comic and “Internet presence” to having a regular job on a show like The Daily Show? It’s such an institution. Do you feel like your comedy has improved being around other funny people? Is it the right step for you right now?

Young-White: I definitely feel my comedy has changed one hundred percent since making the transition to more traditional media. There’s been change for the better – when I was writing on Big Mouth I was around people who had been doing improv or sketch for ten to fifteen years. Just being around that level of extra detail made me realize that I don’t know shit, but it was also really inspiring to see that if you stay at it you can get to that level. Yeah, being exposed to different styles and voices has re-informed me in ways that I can’t really wrap my head around. When I watch my standup sets from a few years ago I can tell a big difference.

BYT: I’m sure you’ve come across some remarkable comics between those two writers’ rooms. And maybe they’re not necessarily mentors, but certainly they’re folks you can bounce a punchline or delivery off of. 

Do you feel like your comedy is inherently political, or was The Daily Show a pivot in a new direction?

Young-White: Honestly, yeah, I think it is. Just the act of getting up on stage and talking in front of people – there are so many decisions that go into that process. Who is the person booking the show? How did you get there? Who is the audience? How long are you talking for? What’s the dynamic with people in the audience? There are so many power dynamics at play inherently in standup that I think that it’s part of the draw of the art form. Comedy in general has that power play that makes it feel exciting. So yeah, I think it definitely is, even if you don’t want it to be.

BYT: One of the things that got me through my time in Chicago was going to see shows at Second City and talking to the performers afterwards. It inspired me to do comedy when I moved to D.C., and really early on I learned the principle that you don’t “punch down” in comedy – you don’t have to punch down to be funny. 

I look at today’s comedic landscape, and so many of the older legends of comedy don’t seem to really get that anymore. And I’m thinking specifically of Dave Chappelle when I mention this, as I just watched his latest special. 

How do you personally feel about what is or should be off-limits in comedy? What delivery is the right delivery? And does that rule of not punching down still apply or does everything go because fuck it, it’s 2019?

Young-White: I don’t think that I’ve been adhering to some list of “this is what I can do and this is what I can’t do.” A lot of people do that and that’s when you’re talking about things that are not necessarily a punch up or down, but tangentially involved. There are some things that I want to joke about that I will be the thing that is being punched down on – it is me. Maybe there is something else involved in it that is priming the audience for it to be a sensitive topic, and there’s some weird tension inherent in it. But it’s my personal experience and I’m personally joking about it, so I don’t understand where this tension is coming from. I feel like that’s the stuff that I find where I don’t necessarily think I’m punching down, but it’s still creating some weird tension even though I am the subject of the joke.

For me, I can see how that could be sort of tenuous, but others? A lot of them probably don’t think they’re punching down. A lot of them truly think that marginalized people have too much power. I don’t think they don’t think they’re punching down – when you say that term to them they’re like “what are you talking about? There’s so many gay people on TV – what are you talking about?” So. It’s very reactionary, a lot of it. Also – there’s always going to be an audience for it and people are always going to feel that way and laugh at those things, but I don’t really know if it’s worth my energy or attention talking about or thinking about those things. Instead of reacting to someone saying something homophobic or any “-ist” thing, let me create a space where the people who are the subject of those things can exist and don’t have to think about those things. [Laughs, sighs] This is like going down a rabbit hole, but by reacting to reactionary – that’s not progress at all.

All your actions and your efforts are still centered around the dominant culture and people who are actively holding back your progress. It’s important to not let it happen but at the same time I would rather do generative work instead. I don’t know – I don’t know. The whole conversation gives me migraines.

BYT: I mean, I can see your point of view. I laughed at parts of Sticks and Stones. But then I saw Hannah Gadsby’s Nanette and it showed me a perspective I never considered before. Everyone’s performing their truth to some degree and you try to process it through your own filter. 

Young-White: Mmhmm. Yeah.

BYT: What are you looking forward to in the next year? Are we going to be seeing some of Jaboukie Young-White, action film star? 

Young-White: [Big laugh] Yeah! Actually I just filmed this movie with Kevin Hart. We’re two police officers and we keep trying to get in our car but the car keeps exploding. [Laughs]

BYT: I mean my real question is if you’re planning to join the Fast & Furious franchise.

Young-White: I mean, shit, I would. [Laughs] I don’t see why not.

BYT: What did you enjoy about last year’s Bentzen Ball and what are you looking forward to this year? 

Young-White: Comedy festivals are so fun – it’s so nice to see people who are true comedy fans bouncing from show to show. Sometimes it’s easy to think it’s not really impacting people, but then you see people who are really, really excited. It’s hard not to feed off that energy and the community of it all, and that’s what I’m looking forward to for this year. And last year’s show was just a lot of fun; JVN (Jonathan Van Ness) always brings out super, super, super stoked people. That energy was so great.