Inside Brandon Rogers’ Darkly Hilarious Universe — From Cult Comedy Icon to ‘Helluva Boss’

“Happiness is the most important thing. The way I can do it is through comedy, putting it on the internet, or even at cons. I judge my experience with someone based on their face when they walk away from me… If they walk away smiling, it’s like I let them take a little vacation from life for a second. At the end of the day, no matter how hard or easy life is, laughing is an escape we all need.”

I had the pleasure of talking with Brandon Rogers. Brandon has built a career on making people laugh at things they probably shouldn’t. With more than two billion views, eleven million followers, and six Streamy Awards, the comedian, writer, and actor has become one of the most prolific digital creators of his generation. His work spans more than thirty original characters, countless viral sketches, a network-backed series, and now two hit animated shows that have made the leap to major streaming platforms. For Rogers, what began as a childhood obsession with storytelling has evolved into one of the most distinct voices in comedy today.

Raised with a fascination for comics, drawing, and homemade videos, Rogers discovered his first artistic outlet before he was even a teenager. Long before YouTube became a household name, he was experimenting with cameras and editing software, carting tapes to friends’ houses just to share his creations. When the video platform finally launched in 2005, the timing was serendipitous. By 2006, Rogers was uploading regularly, and within three years he had joined the site’s partnership program. “The idea that my relatives in another country could instantly watch what I was making — it blew my mind,” he told me. By 2015, his work had taken off to the point where comedy became not only a passion but also a livelihood. He often reflects on the strange fortune of paying for everyday necessities with what was once a hobby that cost him money to pursue.

The turning point came when Rogers’ sprawling sketch universe began finding mass audiences online. His characters were abrasive, satirical, often dark, but deeply memorable: flamboyant suburban moms, inept authority figures, and eccentric personalities that walked the line between absurdity and discomfort. Each was written, directed, and performed by Rogers himself, part of a one-man ecosystem that allowed him to fully control his creative vision. It caught the attention of networks as well. In 2016, he starred in Magic Funhouse!, a Fullscreen and Super Deluxe production, making him one of the first YouTubers tapped to lead a studio-backed digital-native series.

A decade into his career, Rogers began branching further into stand-up comedy and voice acting. One of his most notable moments came when he shared a green room with Conan O’Brien after a show at the Elysian in Los Angeles, a reminder that the Hollywood ecosystem he admired from afar was now one he inhabited. Still, he often describes his trajectory as a “lucky accident,” though one built on years of preparation and relentless commitment.

That preparation culminated in one of his most defining roles: voicing Blitzo in Helluva Boss, an animated series created by Vivienne Medrano. Rogers not only stars in the series but also contributes as a co-writer. The show, alongside its sister project Hazbin Hotel, has developed a passionate cult following, praised for its intricate design, dark humor, and queer representation. In 2024, Helluva Boss became the subject of a first-of-its-kind deal when Prime Video licensed the show while allowing creators to retain full creative control. For Rogers, the distribution shift marked a milestone. “It feels like a legit show now, and that’s wild,” he told me, describing the surreal leap from internet cult hit to mainstream streaming platform.

Rogers views Helluva Boss as emblematic of what happens when creators prioritize storytelling over marketability. Unlike many animated series designed to echo familiar formulas, Medrano’s characters are deliberately stylish, often beautiful or menacing rather than comforting. Rogers believes that authenticity is at the core of the show’s resonance. “It wasn’t made to make shareholders happy. It was trying to be a good show,” he said. That ethos — obsessively fine-tuning details, writing from lived experiences, and never compromising the heart of the project — has mirrored his own approach to comedy.

The projects continue to expand. Alongside his ongoing sketches and his work on Hazbin Hotel, Rogers is preparing the release of A Night at the Park, a sequel to his 2016 short A Day at the Park, which has amassed more than 55 million views. The new installment, shot entirely at night in the wilderness, tested both cast and crew with grueling overnight schedules, equipment limitations, and a constant battle against insects and wildlife. Rogers has described it as one of the most difficult productions of his career, but also one of the most ambitious.

Through it all, he has remained outspoken about the values he believes sustain a career in comedy: humility, authenticity, resilience, and the ability to find humor in darkness. He often jokes that even eating well and keeping teeth white can matter, reminders that levity itself is part of his philosophy. In his personal life, he emphasizes self-care practices as simple as stretching, drinking coffee, and surrounding himself with friends who make him laugh. “A sense of humor is so nourishing to the soul,” he said.

As one of the most prominent queer comedians working in digital and streaming entertainment, Rogers also recognizes the significance of his platform. He hopes audiences see in his work not only laughter but also affirmation that it is possible to be flawed, unconventional, and still deeply human. “Growing up, I wish I had shows like Hazbin or Helluva that said it’s okay to be weird or flawed,” he reflected. Today, with millions of viewers watching his every upload, he sees his greatest measure of success in the smiles of fans leaving conventions or reacting to his videos online. “Happiness is the most important thing,” he said. “At the end of the day, no matter how hard or easy life is, laughing is an escape we all need.”

Yitzi: Brandon, it’s a delight and an honor to meet you. Before we dive in deep, our readers would love to learn about your personal origin story. Can you tell us the story of your childhood, how you grew up, and the seeds for all the great things that have come since then?

Brandon: It’s lovely to meet you. Thank you for taking the time today, Yitzi. I’ve been obsessed with storytelling ever since I was a kid. I used to write, draw, and make comics. I was obsessed with them, and I feel like that was my first real entry into the world of storytelling.

Then I learned how to edit videos and use a video camera, all long before YouTube came out. Once I honed those skills, this website shows up where you can share videos instantly with people. Back then there was this magical word, which I think is now officially out of the dictionary: buffering. Things used to take forever to load.

So the idea that you could finally make videos that didn’t buffer, that would just play instantly on YouTube, was mind-blowing. I was hooked, because before that, the only way I could share my work with people was by going to their house, bringing my camcorder and tapes, plugging it into their TV, and playing it there. The idea that relatives in another country, like in Canada, could watch what I was doing — that blew my mind.

When YouTube came out, there was no other option for me. It was a no-brainer. I just said, “Forget it, let’s start making videos online.” That was in 2006. By 2009, they rolled out the partnership program, and I immediately jumped on it. Around 2015 or 2016, my videos really blew up, and I started doing it full-time.

It’s really cool, because what started as a hobby — something I was ditching class or calling in sick to work to do — has become the thing I now have to do to keep the lights on. It’s amazing when your work turns into something you used to not only do for free, but even spend your own money on just to make happen.

There isn’t a day I fill my gas tank where I don’t think, “Wow, my art — my hobby — is paying for my car to run right now.”

Yitzi: That’s great. You probably have some amazing stories from all the different projects you’ve done and places you’ve been. Can you share with our readers one or two stories that most stand out in your mind from your professional life?

Brandon: Honestly, meeting a lot of the heroes I grew up with, the people who inspired me, has been incredible. I’ve met many of them, whether it’s through premieres, conventions, or just running into them. To even be in a remotely close echelon to where you get to have lunch with them in a green room — that’s surreal.

I did stand-up at the Elysian once, and Conan walked into the dressing room. He had just finished his set and I was about to go on. He came out, covered in sweat, and said, “Nothing will ever beat a crowd that small with that much energy.” I remember thinking, “Oh my god, I’m seeing Conan right after he got off stage.”

There’s a part of Hollywood where, even though I’m in it, it still doesn’t feel real. The myth never really broke for me. All of a sudden, I was just part of it. It feels like a very lucky, happy accident — but of course, luck is really just opportunity meeting preparedness. I was very prepared. I had spent over half my life doing video production simply because I loved it.

I think that’s the key to longevity in entertainment. You have to be obsessed with it. Even people I thought were deeply in love with their work eventually burned out. Especially today, when the pace is so fast and the demand for content is nonstop, it’s easy to burn out. That’s why you really have to love what you do. I’ve loved this my whole life, and honestly, I don’t think I could have kept going without being obsessed.

Yitzi: It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story about a funny mistake that you made when you were first starting and the lesson that you learned from it?

Brandon: Oh my god. It’s nice to watch yourself as an actor. I think a lot of actors don’t necessarily have the luxury of editing their own performances. Now with the way audition submissions are done, we do watch ourselves a lot, but my whole career has been watching and editing myself. Every video I’ve made, I’ve edited. And when you’re cutting together your own takes, the good and the bad, you really learn as an actor what works and what doesn’t.

I think my acting in the first half of my career, and even some of it now, wasn’t great. There are times where I look back and think, why did I do that? Why did I think that was a good choice? There are a lot of videos I’m embarrassed by because of my acting. Sometimes I’ll look back and think, that was a good script and a really good concept, but the acting ruined it. I’ll just take the video down because I don’t want people to see that performance.

It’s scary because back then I never thought I was going to be famous. I was putting bad acting on the internet, not realizing that in 20 or 30 years people could still find it and make fun of me for it. It feels like the world can always see up my skirt at any time, because it’s out there, and some of it is really bad.

That said, I’m lucky because I got to edit my own stuff. I feel like I ironed out a lot of what I didn’t like about my acting very early. I had to face the hard truth upfront and see how bad I was. Now when I edit my work, I see someone who’s much more self-aware on camera, someone who knows how they’re looking and sounding. It’s like working with my past and present self at the same time, editing that past version as I go. Anyway, I hope that made sense. It was a very ADHD answer.

Yitzi: So what’s been the most challenging role or project you’ve taken on so far and why?

Brandon: Honestly, what I’m working on right now is a doozy, and I’m not trying to plug it. I promise. A Night at the Park comes out September 19th, I think, but really, it’s tough. I wrote this massive short film. When I say massive, I mean it’s condensed, not super long, but with a lot of guest stars, actors, and moving pieces. It all takes place at night and entirely in the wilderness.

I picked this month to shoot because the nights are lovely, beautiful, and warm. What I didn’t consider is that other living things come out in the park at night when it’s warm. We’ve been completely covered in bug bites, surrounded by roaches, crickets, and last night there were black widows everywhere while we were filming. It’s horrible being in nature after dark in the summer because everything is out to kill you.

This might be the most difficult project I’ve ever worked on, not just because of the script but because of the environment and the timing. These are overnight shoots, and all of us are working actors during the day. Convincing actors and crew to be part of something that wrecks your sleep schedule is tough, and it’s many nights of shooting. On top of that, carrying equipment through the wilderness is exhausting. Everything has to run on batteries, and we’ve had nights where they’ve died because we’re in the middle of nowhere. You really have to plan ahead.

Almost everything I’ve ever filmed has been indoors or during the day, and now I know why. My legs are just covered in bites. I’m absolutely wrecked right now, and this has not been fun.

Yitzi: That’s great. So yes, let’s talk more about your exciting projects. Tell us about all the exciting new things.

Brandon: Oh, yeah. Well, Helluva Boss, the show, I’m the boss — the one in the title — and it’s going to Prime. That definitely doesn’t feel real. Amazon Prime, September 10th. Depending on when this drops, it may already be out, but oh my god, that’s insane. I’ve never been on a service that big before, and to be the main character of a show like that doesn’t even feel digestible.

It doesn’t feel like it happened, because I always imagined that having a show on a platform like that meant shaking hands in an office with someone in a suit, then being in a trailer, then going to a premiere with a red carpet. And yet this is none of that. It’s just something we made years ago that’s now finally coming out. Maybe we’ll have a premiere, I don’t know, but it doesn’t feel like Hollywood. It’s a weirdly silent big thing.

For me, it feels real when I go to cons and see everyone dressed up as the characters, or when we do panels and the audience is so massive you can’t even see the back of the room. That’s when it hits. But to say, “Oh, it’s on Amazon Prime,” that’s still sinking in. It feels like a legit show now, and that’s wild. Maybe we’ll have a red carpet premiere. If we do, I want you to be there. I’d love to have this interview face-to-face.

Yitzi: You know, Helluva Boss has more than an eight rating on IMDb and it has a cult following. What do you think made it so beloved and captured people’s hearts and minds?

Brandon: I know exactly what it was. It wasn’t made to make shareholders or producers happy. It wasn’t trying to win over an audience. It was trying to be a good show. Viv is a storyteller just like me, and she cares about her characters.

I saw this Emmy magazine spread with all the primetime animated main characters lined up, and right in the middle was Charlie from Hazbin Hotel. She stood out so much among the Homers, Hank Hills, and Bob Belchers. Those other characters, with their big eyes and simple shapes, are designed to feel familiar, to say, “Hey, this is an adult comedy, kind of like The Simpsons.” But then you look at Helluva Boss and Hazbin Hotel, and those characters are designed strictly to look good. They’re meant to be beautiful or menacing. They sell who the character is before you even hear their voice.

I think that’s what extends across the whole show and why it resonated so much. It’s made out of authenticity. It wants to be itself. It wants to be grand, good, and the best it can possibly be. I’ve never once heard Viv, the creator, talk about winning over an audience or hoping people will like it. She doesn’t think that way. It’s always, “Do I like this? Is this story worth telling?”

I approach my work the same way, and that’s why Viv and I work so well together. We’re both asking, “Is this the best version of this story before we release it?” I don’t always get that vibe from other animated series, especially the really successful ones. I don’t feel like someone stayed up late in a diner with a laptop, obsessing over whether a character should do this or that, or hand-drawing the details of a belt, an eye, a gun, or the exact angle of a shot. Every frame of Helluva Boss feels intentional, like a Tarantino image, not just a flat wall with characters walking in and out.

The project is made out of love, and that’s rare in Hollywood. Producers spend a lot of money trying to capture that authenticity because it’s so hard to find. But with Helluva Boss, it’s already there. That’s firmly why I believe the show has done so much better than a lot of other things.

Yitzi: How would you compare and contrast your personal character, Brandon, with Blitzo, the character you play? How are you similar? How are you different?

Brandon: I think the only real differences are that he’s murderous and he likes horses. That’s pretty much where the buck stops. Most of the characters on the show are really just extensions of the actors who play them, and I think that’s a Viv trait. She casts people she loves, and she loves them for specific reasons. Those traits naturally make their way into the characters she creates.

I feel very honored that I get to play someone so tailored to who I am. Usually, a role is created first and then an actor is found to fit it. With Helluva Boss, I believe the actors were considered first, then the roles were created around them, and finally the actors were confirmed. That’s the beauty of it. Blitzo wasn’t a role I had to bend or contort myself to fit. He’s like a pair of shoes made with love, crafted exactly for my foot — and I’ve got a big foot.

He’s possibly the greatest, if not my favorite, character I’ve ever played because he’s the only one who feels like a byproduct of how someone perceived me through the characters I’ve already created. Viv saw something in me, took inspiration from that, and built Blitzo. Now I get to bring him to life. It feels symbiotic, like a role I’ve been unconsciously working on for years. Someone took what they saw in me, shaped it into this character, and handed it back for me to wear.

I couldn’t be happier playing him. It’s one of the greatest experiences of my life. And while I don’t have tattoos and don’t plan on getting any, if I ever did, it would probably be something Blitzo-related, because this project is one of the most meaningful I’ve ever worked on.

Yitzi: What are the messages you hope society takes from the themes of Helluva Boss?

Brandon: Certainly that characters can just be queer, and we can look past that to focus on what they’re dealing with outside of being queer. None of the characters have a coming-out storyline or deal with that specifically. They’re just living their lives and handling struggles. I think that’s why you see, for example, gym bros rooting for Blitz and Stolas — people who might not normally root for gay characters, even conservative folks. You could look at them and say, “Oh, they’re gay,” but the show isn’t about that. It’s about their struggles with their kids, their past traumas, and their personal lives.

I love that it’s inherently a queer story, but that isn’t the driving force. It’s about flawed characters navigating very human challenges. What I hope people take away is a sense of strength in themselves. I hope they feel less alone. Growing up, I wish I had shows like Hazbin or Helluva that said it’s okay to be weird or flawed. None of these characters are perfect, and I wish I had more of that representation when I was younger.

I’m not saying kids should watch it, obviously, but I do hope that at any age, people can feel influenced by seeing characters who aren’t often given the spotlight. And these characters are written from very genuine places. The writers on both shows write from experience. The traumas the characters go through aren’t pulled out of thin air — we write what we know. The audience feels that, and people connect with it because they’ve been through similar things and recognize that pain.

And beyond that, you don’t often see shows with music this good. We have some of the most brilliant songwriters, like Sam Haft, who is a musical genius. He’s just one part of the machine, but every person involved is so talented at what they do. It really was the stars aligning perfectly.

Yitzi: This is our signature question. Brandon, you’ve been blessed with a lot of success and you must have learned a lot from your experiences. Can you share five things you need to be a highly successful comedian?

Brandon: Oh my god.

First of all, no ego. I feel like that’s the first one. What’s the lack of ego? Humility. Humility. I can always tell when someone is afraid of how they look on camera or on stage. It’s unattractive when people are so worried about being attractive. It takes away from authenticity.
And authenticity, that’s another one.
And the ability to laugh at dark stuff. Oh my god, life is so dark. I think we have this inherent belief that comedy should be light because it’s distracting us from the dark. But really, learning to laugh at the darkness and live in the darkness and be fine with it is powerful. Obviously, there’s a matter of taste and punching up or down, but I think having a dark sense of humor and being comfortable joking about life’s issues is a very healthy mindset. Was that three? Let me think, two more.
You know what? Eating is a big one. You can’t be funny on an empty stomach. I’ve tried it, and I feel a lot funnier when I eat.
And then the last thing… to be a good comedian, teeth whitener. You’re going to be smiling and laughing a lot, so I think having nice white teeth is important. You want your smile to really read from a mile away. So that’s a good one. Anyways.

Yitzi: Brandon, can you share some of the self-care routines that you do to help your body, mind, and heart to thrive?

Brandon: Washing my face and brushing my teeth. Basically neck-up stuff. As long as that’s all good… stretching too. Coffee is huge. It keeps me awake, it keeps me regular, and honestly, I drink so much of it. I was as white as you when I started drinking it. Laughing is another big one. That’s how I judge my friends. I only have friends that make me laugh. If you can’t make me laugh, that’s probably why I don’t hang out with you. A sense of humor is so nourishing to the soul. It’s like how humans can sniff each other’s butts — by testing someone’s sense of humor. It tells you so much about their intelligence and whether I want to spend time with them, converse with them, or share opinions. If someone can be funny, it bumps them much higher in my book. So yeah, laughter is definitely a self-care routine, and having friends who can amplify that is a great one too.

Yitzi: This is our final aspirational question. Brandon, because of your amazing work and the platform that you built, you’re a person of enormous influence. If you could put out and spread an idea or inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Brandon: I think making other people happy in any way. Happiness is the most important thing. The way I can do it is through comedy, putting it on the internet, or even at cons. I judge my experience with someone based on their face when they walk away from me at a con. If they walk away smiling, it’s like I let them take a little vacation from life for a second. The same goes with videos. I watch the reaction videos to what I make because it’s nice to see people laugh. Some people will cry, some people will literally piss their pants, and I get to watch this happen. It’s so nice to see that I’ve infected someone with something positive. At the end of the day, no matter how hard or easy life is, laughing is an escape we all need. I really appreciate it when others make me laugh, and being able to give that out on a large scale is a gift. Like you said, large influence — I’m glad it’s that kind of influence, because people can have all kinds. I’m really happy mine is associated with laughter. That’s all that matters at the end of life. So, yeah.

Yitzi: Brandon, it’s been such a joy to meet you. How can our readers continue to follow your work? How can they watch Helluva Boss?

Brandon: Amazon, September 10th, Amazon Prime. It’ll be right on there. You can even make your profile photo my character. Also, just any search bar, any search hole, type in Brandon Rogers and I’m sure something will come up. But really, thank you for taking the time to allow me to talk about myself. Thank you.

Yitzi: You’re an amazing interviewee. You’re really talented, and you have a very empathetic heart.

Brandon: Oh, Yitzi, thank you so much. That really means a lot to hear. I had a great time doing this. Thank you.

Inside Brandon Rogers’ Darkly Hilarious Universe — From Cult Comedy Icon to ‘Helluva Boss’ was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.