Jess A Mess

What Happens When You Build on Borrowed Land

”Good morning it’s Jess With the Mess and my news is real!”

Being real is underrated. So when you come across someone who’s confident and charismatic without trying too hard or toning themselves down, you instantly fall in love and find yourself rooting for them. This is exactly how I feel about comedian Jess Hilarious.

The Jess We Fell in Love With

From 2015 to 2017, Jess had me in a chokehold. I laughed out loud and overshared just about every video she posted. She was raw, unfiltered, and funny in a way that didn’t feel forced. That thick unapologetic Baltimore accent, no wig wearing, on her way to drop Ashton off at school made Jess as relatable as a close family member. Jess was special. And we knew it.

I am not quite sure what led Jess to press record and share her world with us, but like 106 n Park or Ms. Cita from BET she had our time and attention.

Jess Hilarious was ahead of her time—funny before folks figured out how to market her funny. Somewhere between being real and being palatable, something went missing. That middle space…maybe that’s where the tension began. That’s where we started to lose her or, where she started to lose herself.

The Pressure to Evolve

Jess isn’t the first vial comedian and she wont be the last, Creators and skit makers like King Bach, Haha Davis, B.Simone and other al gained popular in similar fashion by stopping our scroll and making us laugh. But sometimes, people only see your work because of how you choose to be seen.

In a world where the internet and media are constantly shaping how we view people, the way you present yourself—your image and persona—can be just as important as the work you create.

As she moved into mainstream spaces, there was pressure to adjust that authenticity to fit into a more polished, mainstream mold. And that’s the tricky part: the balance between staying true to who you are and trying to meet the expectations of the industry, your audience, or even the platforms you’re on. When that happens, the version of you that people fell in love with may start to fade, and the work that made you stand out can get lost in the shuffle.

And in Jess’s case, that choice may have led her to a seat at the wrong table.

Controversy and Clicks

Jess Hilarious has had her share of messy moments; moments that reshaped her image and impacted her confidence. Her highly publicized relationship with fellow comedian Kountry Wayne was full of ups and downs, making her personal life as much of a spectacle as her comedy. This constant exposure started to feel like a pressure to conform, pulling her away from the unfiltered, real woman we fell in love with.

Her time on Wild 'N Out showcased her talent, but when she left amid rumors of fallout with castmates like Justina Valentine, it was clear that the structured, industry-driven space didn’t quite align with her free-spirited vibe. Not to mention her funny was encrypted and felt inauthentic. Perhaps the right idea but the wrong execution. Then came her controversial comments about Chadwick Boseman, which sparked massive backlash and shook her credibility. It was a moment that forced her to reckon with the balance between authenticity and the expectations of fame.

Things got even messier with her naked photoshoot with her young son, which sparked intense debate. Whether seen as empowering or distasteful, it highlighted the struggle women face in reclaiming their bodies while under constant scrutiny. Jess’s decision to get a BBL added another layer to the conversation. Was it about self-confidence or pressure to fit a societal standard?

Each of these moments showed Jess trying to balance the real, unapologetic woman we loved with the pressures of fame. In doing so, she lost touch with the very authenticity that made her relatable, and in trying to keep up with industry standards, she drifted from the unapologetic energy that first had us rooting for her.

The Pivot That Missed the Mark

Jess was on the come up for sure. Taking her acting more seriously, we got to see her shine on the big screen in 2 Minutes of Fame and Rel. Jess was making moves but nothing she did was taking off as quickly as that first launch into the spotlight. Too soon to be hitting a career plateau, Jess made a necessary pivot.

Between 2021 and 2024, as podcasts became increasingly popular, Jess Hilarious joined the trend by launching her own show, Carefully Reckless, in January 2021. The podcast quickly gained traction, with Jess's unfiltered, raw, and humorous take on everything from pop culture to listener-submitted dilemmas. Her unique approach resonated with listeners, earning her a solid fan base. However, it was not what anyone expected of Jess. She was seemingly shedding her unfiltered persona and becoming more polished, scripted, and, at times, overly calculated. Yet this made her an excellent candidate for The Breakfast Club.

Jess on the Radio

When the announcement came that Jess Hilarious was joining The Breakfast Club it felt like a moment of triumph. For anyone who’s followed Jess's rise from viral comedian to mainstream star, this was supposed to be the next logical step. It’s The Breakfast Club, a legacy show, a cultural juggernaut. Being a co-host on this platform is a big deal.

But this move was not without its own controversy. Days before the official announcement Jess took to her social media with a cryptic message indicating she would be the new permanent host. That announcement was swiftly removed. It once again jeopardized jess’ credibility making her look foolish until days later when The Breakfast Club made the official announcement.

Despite a bump start, for a while, it seemed like the perfect match. Jess brought her energy, her humor, her unfiltered personality.

But then the tension started to simmer.

As Jess settled into her role, it became clear that the dynamics at The Breakfast Club weren’t quite as seamless as many had hoped. The show’s energy, often chaotic and brash, didn’t always welcome that same energy from Jess. While her chemistry with her co-hosts was evident, there was a subtle shift from the Jess we first fell in love with. Her humor, which was once spontaneous and free-flowing, began to feel more scripted. Her off-the-cuff remarks, which had earned her millions of views, were now being carefully curated.

In a way, Jess was starting to lose herself in the structure of The Breakfast Club. The pressures of mainstream radio, the expectations of a well-established show, and the industry’s demand for a polished, more calculated version of her started to dull the raw, vibrant personality that made her a star in the first place.

And as the tension between her real self and the expectations of the platform grew, we couldn’t help but wonder if she was stepping into a space that wasn’t really designed for her voice. The Breakfast Club had always been about pushing boundaries, but now, it seemed that in trying to find her place, Jess was being asked to soften her edges just a bit too much. What made her stand out in the first place—the fearless, messy, and unpredictable energy—was getting lost.

The Balancing Act

Most career women fear getting pregnant or even delay starting a family to climb the corporate ladder. Jess was no different. As a single mom with a few public failed relationships, she tried to keep her new love and family life private. But you can only hide a growing belly for so long. The moment she announced her pregnancy, you can bet the show was making plans to maintain its ratings and meet their bottom line. Despite Jess' presence, you have to understand that there are many talented personalities out there who can do radio. As it goes in corporate, one day you’re in, and the next day you’re being replaced. No job is secure.

When Jess returned, it was clear that the energy had shifted.

The Trap of Staying Relevant

Recently, Jess made headlines for confronting her co-hosts on The Breakfast Club after feeling left out during maternity leave. (You can read the full piece here.) It was uncomfortable, raw, and real—but it also felt like a moment that revealed something bigger about the spaces Black women try to make work for them, and the cost of trying to hold onto fame in rooms that were never designed for them in the first place.

Perhaps, with a combination of reading comments online and overhearing break room chatter, she began to feel undervalued and overlooked. It seemed as though she was no longer the top priority, and the pressure of competing with others who might take her spot loomed large. This tension, mixed with frustration, led to her on-air rant. Her outburst was raw, unfiltered, and painfully honest—a moment of vulnerability that exposed the internal struggle of trying to maintain your worth in an industry that can easily discard you.

But beyond just the rant, Jess’s struggle was a deeper battle with identity. As a new mother and public figure, she was caught between two worlds: the fierce, unfiltered woman we first loved, and the polished, corporate co-host that her new role demanded. The show required a level of conformity that Jess’s authentic, boundary-pushing persona didn’t quite fit with, and trying to adapt to that new reality meant compromising the very thing that made her relatable and beloved. She had to reconcile her natural energy with what was expected of her on-air, and in trying to mold herself to the corporate radio world, she was unknowingly risking the authenticity that had driven her success.

Attempting to fit into a space that wasn’t built for her led Jess to lose the magic that made her stand out. She tried to adapt, to show that she could juggle both motherhood and a high-profile career, but in doing so, she lost a bit of herself in the process. Her attempt to maintain relevancy in a highly competitive industry ultimately ended up being a mistake for her personal brand. In the rush to stay relevant, Jess gave up pieces of the very essence that made us love her.

Fitting In at the Cost of Belonging

Sometimes, in the pursuit of staying visible and relevant, we pivot in ways that don’t align with who we truly are. We compromise our values, contort our personalities, and adapt to environments that were never meant for us—just to prove we’re worthy of the space we’ve been granted. But what many don’t realize is that visibility without autonomy is a trap. It’s a false sense of achievement, where we’re seen but not empowered, heard but not respected.

When we’re constantly chasing opportunities on borrowed land—platforms, shows, and industries that aren’t designed with our success in mind—we lose sight of what really matters: ownership and true influence. The more we rely on these external systems to validate our worth, the more disposable we become. At the end of the day, when someone else holds the power to decide our value, we’re always left fighting for a seat at the table instead of owning the table we sit at.

This is where Jess Hilarious, like many creatives, finds herself in a precarious position. Her path could’ve been different. She had the talent, the personality, and the audience. Jess should’ve had her own show by now. She deserved a platform where her voice, her perspective, and her narrative could shine—free from the constraints of a legacy radio show that’s barely figured out how to make space for women, let alone Black women juggling the complexities of motherhood, personal brand, and visibility.

The problem with trying to stay relevant on someone else's terms is that it often leads to a constant battle for attention and validation. Rather than leading with your own voice, you’re fighting to fit into a mold created by someone else’s vision. It’s a dangerous game, because the more you try to contort yourself to fit in, the more you diminish your own power. Jess, in her quest to prove she belonged, inadvertently placed herself in a position where she was competing for the spotlight in a space that never fully understood her, or the full scope of her potential.

Jess Deserves It All

Jess may not know this, but she doesn’t need The Breakfast Club to be successful.The truth is, she could—and should—have her own show, in the vein of Wendy Williams or even Saturday Night Live. Can you imagine that? Jess with her unfiltered humor, her perspective, and her unapologetic personality, running a show on her own terms. That’s the future I see for her.

The fact is, Jess has more than enough talent and influence to build something unique outside of The Breakfast Club. With her already massive following and broad appeal, she’s proven that she’s a force in the entertainment world. The key now is to stop seeking validation from spaces that weren’t designed for women like her and start creating her own platforms. Jess doesn’t need to fit into someone else’s box—she can create her own.

As a personal branding expert, here’s what I would suggest for Jess moving forward:

1. Reinvent Yourself

   Embrace her multifaceted experience. She has the talent and versatility to dominate any medium she chooses. Why settle for a corner seat on a legacy radio show when she could be leading her own program, or better yet, breaking new ground in television or digital media?

2. Reclaim Jess with the Mess.

   She needs to lean into her authenticity and just go for it without holding back. Whether it’s comedy, talk shows, or something entirely new, she has the power to create a dominant space for herself. And most importantly, Jess needs to stop competing and start commanding. She's already proven her worth, now it’s time to take control of the narrative and lead with her own voice.

3. Build a Community, Not Just an Audience

   The real power lies in building a community not just an audience. Jess has a loyal following, but now it’s time to take that loyalty to the next level. She can leverage her authenticity and realness to create a space where her fans can engage with her and each other, forming a strong bond. This community can extend beyond social media and into exclusive content, live events, merchandise, and even partnerships that speak to the values and experiences she shares with her audience. By fostering a deeper connection with her followers, Jess would solidify her brand in a way that’s unshakeable, empowering her to have more control over her career, choices, and content. She’s already built a fanbase; now she needs to build a movement.

Jess Hilarious is a force, but she’s been playing by rules that weren’t made for her. From the very beginning, she’s had to navigate a space that wasn’t designed to amplify her voice or celebrate her uniqueness.Jess has built an empire by being unapologetically herself, and the more she embraces that, the less she needs to play by anyone else’s rules. It's time for her to redefine the game, carve out her own space, and show the world that success doesn’t require fitting in; it requires standing out.

I am rooting for her and you.