Comedian Zainab Johnson talks Prime Video's Upload, a stand-up's worse nightmare, and navigating taboo topics

Johnson performed a tax-focused stand-up set at H&R Block's 'A Kickoff to Tax Season 2025 proving that humor can be found even in the most unlikely corners of life.

Zainab Johnson at H&R Block Event
Zainab Johnson at H&R Block Event

Tax season can be anything but funny, but H&R Block brought a bit of levity during one of the most dreaded times of the year for the everyday earner, creator, and small business owner alike through H&R Block 'A Kickoff to Tax Season 2025' event.

This invite-only event was held in Hell's Kitchen and boasted informative sessions included 'What You Need to Know About Tax Season 2025, presented by The Tax Institute at H&R Block', 'Tech Your Taxes: From EVs and Solar Panels to AI and DIY Filing', and 'Tax Talk for Creators and Entrepreneurs: A Small Business Panel Discussion with Block Advisors by H&R Block'.

At the end of the evening, as a part of 'It’s Better with Block: A 70th Anniversary Celebration', comedian and actress Zainab Johnson (Upload, A Black Lady Sketch Show) proved that she knows a thing or two about taxes. Known for her sharp wit and ability to turn everyday frustrations into comedic gold, Johnson chases topics about everyday life, dating, family, and transforms them into stories (like ones found in her Prime Video special Hijabs Off) and anecdotes all with a fresh perspective.

Culturess sat down with Johnson to learn more about her upcoming projects, how she navigates the comedy world and how it feels to tour across the nation. Whether you're a new-found fan or a loyal follower, be prepared to laugh and learn more about this Harlem-native.

Culturess: Congrats on Upload! I love the show. This is the fourth and final season [coming up], and I always wondered with comics, being that you are on stage solo versus being in a show, what's that mindset that you have to have when you're in a cast as opposed to being on stage?

Zainab Johnson: When you're doing stand-up on stage, it's a solo act for the most part. When you step on a TV show, especially Upload, it's an ensemble. You don't always get the joke. Sometimes you have to be the one to feed the information. Sometimes you are the one to have this suspenseful moment. You learn, or at least I learned, very quickly, we are all a very important component on this vehicle and everyone [matters]. Not just the actors, the writers, the directors, but the production assistant, the health crew, the people who feed us. They are every single part of us. Every single link is so important. Then together, as long as everybody shows up and does their part, then the vehicle moves. That's why we had the wonderful pleasure of being able to move four seasons.

Greg Daniels [Series creator of Upload]; He's a genius. He's too good.

Zainab Johnson: He's too good. He needs to settle down! [laughs] When you get to know him on a personal level, he's so humble and so nice. He's so reasonable and collaborative. It's like: 'How are you this way when everybody wants a piece of you?' It's beautiful.

You are a born and bred New Yorker so you're aware of the New York comedy scene and how audiences can be tough. Has there ever been a particular moment or show that stuck with you where the audience was interested are unique in a certain way?

ZJ: I really do feel like New York has some of the best comedy audiences in the world because New York is such a diverse city. New Yorkers are so savvy. If you grew up in this city, if you live and work in this city, then you are forced to have a higher level of common sense and awareness than a lot of other people in other places. New York just loves comedy. For the most part, it's tough because they get a lot of the best. It's 'Come and be the best.' Instead of looking at it like, 'Oh, I'm being prepared to be great.' I quote Jay-Z: 'If you can make it here, you can make it anywhere.' I feel like that applies to comedy as well.

I remember a time...this happened in LA. I'll never forget. I was hosting. It was early in my career, maybe one year in, and I was doing five-minute sets, five-minute sets at The Comedy Store. I finally elevated enough to get a main 12-minute set. I thought: 'Well, they've seen my five minutes over and over and over again. I got to do all new material.' I bombed. I bombed so bad that even my friends were just like, 'Oh, no. We should go, right?' I'm like, 'Let's stay and enjoy the show.' They're like, 'No, we should go. Then, the funniest thing about the night is for the first time, since the host is usually right on the side of the stage ready to get you off the stage, that particular night, as I'm bombing, they 'light' me early which means I have to get off early. Which is fine. I needed to go. The host was nowhere to be present. So, I just had to sit in the awkwardness of doing bad, them wanting me to leave, but not being able to go in there.

If I ever was in that moment, it'd be even worse for me. That being said, you have a unique voice in comedy! Who or what inspires you to keep pushing boundaries, tackling topics that maybe are taboo for some people?

ZJ: My goal as a comedian and in this business is to be the figure that I wish I had when I was a kid. Part of that is being vulnerable enough to talk about what we're all experiencing, however good or bad. I always feel more comfortable in a room when people acknowledge the element. Not that I am intentionally looking to be provocative or anything like that. I'm just looking for a balance; Enough truth for us to remain sane.

Speaking of tackling somewhat difficult topics: tax season. We're always talking about it, but how do you navigate tax season as an entrepreneur?

ZJ: Let me tell you, I ain't never done jokes about tax season. This is a first. I'm happy that I was able to be a bit truthful about my tax experience because it's not a fun thing. It's like a wanting to. I think it's the same sentiment when people are like, I'm scared to go to the doctor because they're scared to find out. It's like, as long as I don't go, it's fine. For the most part, most people get a reason. Most times, it's good. That little percentage of, 'Oh, no, have I not been life-ing right, can be a little bit daunting. If I'm being completely honest, finances have always been taboo.

People are afraid to be embarrassed. For me, I'm really happy to be here and expose myself, expose my younger self. Just for a bit of transparency. Thank God for services like this, because I thought I should have said this on stage. As a young adult, as a kid, I thought you needed to be rich to have an accountant. I'm really grateful that businesses like H&R Block are available to walk us through. It just seems like a chore. I'd rather wash dishes!

You have some tour dates coming up: Pittsburgh, Chicago, Toronto, and you're coming back to New York. What's the energy performing in these cities that you know have an electric audience?

ZJ: My goal when I get on stage is to bring people into my world. As much as I'm coming into your city, you are coming to my show to be immersed in my world. I don't know if I have a feeling about it, but I do have a hope, and my hope is just that everybody shows up wanting to have a good time.

You can keep up with Zainab via her website and Instagram. Keep up to date with Culturess for more female-centric entertainment news and opinions!