“It’s not funny, but I have to laugh,” explains cultural presence Jaboukie, reminiscing on his journey from internet star to successful writer, comedian, and actor. Our interview begins as we discuss the fickleness of experiencing digital stardom and the new American Dream: “...with the internet, it’s fun while you’re doing it, but the trade-off is overexposure. And then... a devaluation of what you’re doing. At the end of the day, what’s really real are those palpable things that I’m kind of doing now—they’re palpable by necessity.”

If you were around from 1994 to 1999, you experienced the world’s sharpest spike in technological advancement, the proliferation of the internet. Some of the most honest portrayals of the modern human experience live online. But as relatability became profitable, the integrity of online content was challenged. For Jaboukie, the internet “was only fun for like two years, to be honest.” He continues, “A part of me laments the internet, the potential that the internet had, because I remember as a kid, I really felt like, ‘This is going to be the wild, wild west. This is going to be a whole new world. This is going to change everything.’ And especially being a young queer person, the internet is like your ticket out of your surroundings, so much so that LGBTQ country is the internet. That is the gathering place. And the loss of that community is the one thing where I’m like, ‘That really sucks.’”

Even with loss of authenticity, the internet remained vibrant. It could award you entry to the largest talent show on earth. Breakout stardom, like Jaboukie’s experience, was now possible from your bedroom. Jaboukie became somewhat of a revolutionary Twitter icon. His reach went as far as The Department of Justice: “I think the FBI tweet is probably the most iconic moment... I set the bar pretty high for myself there.” Jaboukie’s impersonation of the FBI’s Twitter gained him notoriety and an indefinitely suspended account. His stunt lives on in screenshots.

As the prominence of “the influencer” rose, the gap between civilian and celebrity shrunk. As compared to classic celebrity, “internet fame” was much more accessible but far less lucrative. Still, influencers have become modern icons although they remain largely unpaid. “I’m just fucking around. I’m just having fun, you know, and there’s a low stakes to it that I love because I just love having fun and fucking around! But on the other end of that, there is a stigma that comes with doing things for free, you know. Unfortunately, it is what it is, but I have fun.”

Jaboukie is now reaping the real benefits of his talents. He landed writer’s room gigs at The Daily Show and Big Mouth, acts in Max’s Rap Sh!t, and has become a name in comedy. When prompted, Jaboukie recalls the funniest thing he has ever said: “I did a high school performance of The Miracle Worker... And I ad-libbed a line. It got like a three-minute laugh break and that was the moment where I was like, I want to be a comedian. I got addicted to the sound of laughter.”

2020s media is largely insufferable. “There’s so much writing and material out there right now, which is just made for what will be easy to consume. I’m starting to get kind of depressed because I need more than that... There’s a sheen of this toxic positivity where there’s a truth that you’re running away from because it is uncomfortable... Even with those things there’s a way to express it that kind of sublimates those negative feelings, but doesn’t pretend like they don’t exist. I think I’m trying to move toward lucidity, clarity, honesty, I think that that’s kind of like a North Star [for me].”

We digress for a moment to acknowledge an interview in which he was described as, “starkly millennial.” “I mean, millennial is the slur now, so that’s kind of embarrassing. I feel like the generational divides are becoming less and less relevant now that we’re in just a perpetual state of boomer rule. I feel like as Gen Z, once you age out of the market where all of their products are targeted toward you specifically, then it’s like, okay, you’re just in oppression land with everybody else who can’t afford a house or health insurance or like, you know, a job that doesn’t make them want to kill themselves.”

As we discuss the freedom of aging out, Jaboukie responds to what the future of the internet may be: “We are now paying the debts for all of that fun we had for two or three years. All the investors are like, ‘Okay, where’s our return? Where’s the money now?’ And they never had a plan to make money. They were just all trying to be Mark Zuckerberg. And, now we have to deal with their shit. So I think, there is hope on the horizon. I think things are moving into more of a group chat, like a Discord [or]... like even an old school blog style, like Substack blowing up. In terms of the trajectory, it’s sad. I feel like, as someone pushing 30, I remember the tail end of the 2000s when you would just go hang out at the mall because there really was not shit else to do. And it’s like you’re trying to turn this money church into a playground, like a place where you just go be rich and spend money and you’re trying to have pure genuine fun. That’s what the internet is now. A big ass mall.” 

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Photographed by OK McCausland

Styled by Britt Theodora at The Wall Group

Written by Erica Brown

Grooming: Evy Drew at Exclusive Artists using Koh Gen Do and JVN Hair

Photo Assistant: Jackson Chihuly

Styling Assistant: Alexandra Crown

Location: Moxy Brooklyn Williamsburg