Confident and Unapologetic: Jess Hilarious Speaks Her Truth

In this exclusive interview, Jess Hilarious, the multi-talented comedian and social media sensation, opens up about her journey to success, the challenges of her new role on The Breakfast Club, and her unfiltered thoughts on everything from handling internet controversies to navigating the ever-changing landscape of the entertainment industry.

With candid insights and a dose of her signature humor, Jess shares the highs and lows of her career, her thoughts on the power of Black entrepreneurship, and the pivotal moments that have shaped her path. As she discusses her future aspirations and the projects close to her heart, Jess offers a glimpse into the drive and determination that have made her one of the most relatable and influential voices in comedy today.

Kevin: When you started on The Breakfast Club, the whole process of letting people know that you had made the cut and that you were going to be on there, whose idea was that? Like, creating that speculation that you had the job before you actually did.

Jess Hilarious on Navigating Controversy in the Public Eye

Jess: Oh, it wasn’t really anybody’s idea. I actually take blame for that (jumping the gun and telling everyone that she got the job before it was officially announced). I wasn’t supposed to do that, but I didn’t care. I wanted to put them under fire. But to go with it, I think it was Charlemagne’s idea. It wasn’t the program director (Thea Mitchem); it was Charlemagne. They decided to run with it. When I first announced that I was on, I didn’t hear from anybody—Charlemagne, iHeart, the program director, Envy—no one. So I was like, “Oh man, maybe I shouldn’t have done that,” but I didn’t realize it would go that viral. I just wanted to light the fire under them because I felt like they were taking too long. At first, they didn’t want to give me what I felt I was worth. And this wasn’t just a simple move; I had to relocate to the tri-state area. I have a child and another on the way, so it was a lot.

Kevin: So it was all real?

Jess: Yeah, it was real. I didn’t hear from any of them after I made the announcement. iHeart finally hit me back after about three weeks, and then they wanted to move forward. I was mad at Charlemagne for a while because nobody had reached out to me. Everyone just stopped talking to me.

The Announcement That Shocked the Industry: Jess Hilarious on Her Breakfast Club Role

Kevin: I remember you got on stage and made the announcement in Baltimore. Charlemagne is notorious for pulling stunts like that, like with the Atlanta situation (where he said a blog announced they were off the air in Atlanta). Thea and Doc Wynter (President of R&B and Hip Hop for iHeart) are usually quiet about these things. I thought it was all a setup.

Jess: A lot of people did, and a lot of people fell into the trap and started running their mouths too. I stayed quiet. Some of the same people who congratulated me when I prematurely announced were the same ones bad-mouthing me later.

Kevin: That’s funny I also saw videos where some YouTube channels denounced TBC saying the show had fallen off when Charlamagne announced the show was canned in Atlanta (but it actually moved to a bigger signal). What’s your favorite part of doing the show versus what you expected?

Jess: Honestly, I expected exactly what it is. But what I didn’t expect is having to do interviews. I cannot stand doing interviews.

Kevin: Really?

Jess: Yeah, I don’t like doing it right now. I like being interviewed, but I don’t like being the one asking questions. It means I have to do research on so many people, and I don’t want to sit in front of someone and not know anything about them. I feel strongly that when someone comes in for an interview, you need to know who they are, at least the basics. We interview a lot of politicians, doctors, and not just entertainers. Politics isn’t my strong suit, and I try to avoid political interviews because I don’t know what to ask. If someone asks me something political, I’ll just say, “I don’t know.”

Kevin: Now that you mention it, I’ve noticed that when certain people come on, you’re very quiet. Like when TD Jakes was on, you just sat back and let Charlemagne and Envy take over. I wouldn’t have guessed that if you hadn’t mentioned it.

Jess: Yeah, with certain guests, I just don’t know what to ask, like with Bill Burr. I’m a fan of his, but after I fan out and say hello, I’m like, “What the hell do I ask you?”

Kevin: How do you like doing the research for your news each day?

Jess: I like it. Before I did Breakfast Club, I was doing “Jess with the Mess” on my social media. I’d search for the latest news on the blogs, and I had celebrity associates who’d tell me things to report. Now at Breakfast Club, I’ve expanded it to cover more than just the latest gossip. I want to talk about other things happening in the world, like the new STD that looks like ringworm. We have 91 million listeners on the podcast, and a lot of people still listen to the radio. I want to bring awareness to important topics, not just celebrity gossip.

Kevin: I was telling Charlemagne and Doc during your trial that you were the one they needed to bring in. The chemistry is great. I’m glad they brought you in. I’ve also noticed that you’ve had to battle a few people. Where do you think that energy comes from?

Fairness Above All: Jess Hilarious’s Commitment to Standing for What’s Right

Jess: I think it comes from the fact that I’m unapologetic and opinionated. I stand on what I say, no matter what. I’m on the side of fairness, no matter who you are or what community you’re in. But not everyone likes what I say. I’m a confident young Black woman, and a lot of people attack that. People like confidence, but not too much. They don’t want you to be too cocky, too confident, or too successful. I think that’s why I get attacked a lot—I don’t shut up for anyone.

Kevin: Besides the Chadwick Boseman situation, is there anything you regret saying (she made fun of the way he looked before anyone knew he had cancer which he later succumbed to)?

Jess: No, I don’t regret anything I’ve said or done in my career, except for the Chadwick Boseman joke. That taught me that you never know what people are going through. I honestly thought he was losing weight for a role, so I made fun of it. Then he passed away less than a month later, and I felt like the biggest butthole ever. I was slandered online and I was mad at myself. He was such a legend, and everything he did was amazing. He worked through his illness for years, filming while he was dying. That bothered me for like two years. I almost canceled “Jess with the Mess” after that, but I didn’t know. I don’t regret anything else I’ve said, though. I say what I feel all the time.

Kevin: Is there anything you regret not saying?

Jess: No, I think I’ve said everything I needed to say. I’ve got more coming too. But I’ve learned with the new internet that you can’t say what you want online anymore. These big corporations and the politics of everything—they play into sensitivity a lot. Everyone has a voice now, so it’s easier for someone to strip you of sponsors if they act like they’re offended. I’ve learned to be careful about what I say online, but I still say it in other ways.

Kevin: As you mentioned, corporations are very sensitive to controversy, but we’re also in an age where Black people are finally learning to run their own businesses and have their own platforms. Do you think we understand the power and influence we have without corporations?

Jess: Not everybody does. Somehow, our people are the only ones who look for validation from everyone else but each other. If more of us stopped doing that and poured into each other, we could be greater than any other race. But it’s going to take more than a few of us. We need to get that leadership mindset. Even when it comes down to awards, why are we working so hard to be validated by these organizations? They measure our success and tell us what it is, but they need us more than we need them.

Kevin: That’s why I admire Tyler Perry. His work is not for everyone but his business acumen is second to none.

Jess: I get you. He’s brilliant.

Kevin: The other question I have is, how did you get your start? I don’t know if this is correct, but do you think you got a boost from COVID when you were doing your videos online?

Jess: I got my start way before COVID. I probably did get an extra push during COVID because I’ve rebranded three times since I came out. I started doing videos back when Instagram had 15-second videos. My very first sketch was the Maury Povich “You are not the father” sketch. That went everywhere, and then Nick Cannon called me to be on Wild ‘N Out, which gave me a push. Then I did Rel on Fox, where I had a lead role. I kept doing my content, and then COVID hit, and everything dried up, but I was still touring. I never had to sit down for more than maybe a month. I wasn’t touring as much as before, but I was still selling out shows. During COVID, I rebranded “Jess with the Mess” and started creating series because there was nothing else to do but be online.

Kevin: What kind of series did you create?

Opinionated and Proud: Jess Hilarious on Speaking Her Mind in a Sensitive World

Jess: I created several series. One was called House of Jewels, where I played five or six characters. Another was Lil Dude, about my son and how me and his father co-parent, told from his perspective. There was Co-Parenting Therapy with me and my son’s dad, and another series called Justify, about me being on the road, shot like The Office documentary style. I also did Reckless Discussions, a talk show with three of my family members about reckless topics. I put all these series on YouTube.

KR: It must have been time-consuming to create all that content.

JH: Yes, it was. I don’t do as many skits now because it’s oversaturated. I focus on writing and pitching shows to networks. I’m not giving away my hard work for free anymore.

KR: Was it hard to transition from internet comedy to stand-up?

JH: Not for me. I started doing both around the same time. My god-brother encouraged me to do stand-up, and I fell in love with it. It wasn’t hard for me to transition, but I know it is for others.

KR: What do you hope to accomplish with the Breakfast Club?

JH: I want to use it as a stepping stone to my own TV talk show. I don’t plan to stay in radio forever. This is a pivotal moment for my career, setting up for the next big thing.

KR: Anything else you want to add?

JH: I have a book coming out about co-parenting with my son’s father, an eyewear line called Messy Vision, and an athletic line. I have a big project in Baltimore that I can’t talk about yet but it’s going to be amazing.

KR: I saw your video about your boyfriend. People really thought he was Brittney Griner!

JH: Yes, that was hilarious. People grab onto anything these days.

KR: I’m very proud of you and happy to see your success. You’re going to be a very big star. It was a pleasure interviewing you. Take care.

JH: Thank you so much, Kevin. Take care.

See the entire interview with more segments on our YouTube channel