This “Worst Cooks in America” alum and TikTok famous comic is currently taking part in NYC’s next favorite immersive theatrical experience, while hosting a brand new platform at Red Eye: Charles Osborne!
Thotyssey: Hi Charles, thanks for talking to us today! How has summer been treating you so far?
Charles Osborne: Dude, I’m having the time of my life. I’m performing six days a week in Masquerade, the new immersive Phantom of the Opera. I’m doing comedy one day a week at Red Eye. I’ve also gained ten pounds, two lovers, and zero sexually transmitted infections. What’s not to love?
That is the life! What can you spill about Masquerade? I recently spoke to someone working behind the scenes, and it sounds like an amazing experience!
I wish I could tell you more, but I’m not allowed to share any details. I will say it is by far the coolest show I’ve ever done, and I’m so grateful to be a part of it. It is truly extraordinary.
You’re a writer, performer and producer; you do cabaret, comedy, theater… what’s your origin story as a performer, and where are you from originally?
I’m from the Queen City, henny — Charlotte, North Carolina! I went to Northwest School of the Arts for high school, the same arts high school as Renée Rapp and Eva Noblezada. Then I went to UNC School of the Arts for college, which was basically Hogwarts for theatre nerds. I’ve been lucky enough to work in theatre my whole life, all over the country: the Hollywood Bowl, Lincoln Center, the Port Authority men’s room. But I was surprisingly late to cabaret and comedy.
I started writing when I moved to New York, but it was mostly plays, operas, and musicals with the composer Leo Hurley — one of which is on Spotify, another of which helped bring down the anti-trans “bathroom bill” in my home state of North Carolina.
I started developing my own sketch comedy cabaret shows in 2016, which was the first time I’d ever written a role for myself. That turned into several nightclub residencies, most notably at Club Cumming with the hysterical Dorothy Bishop. In 2019, comedian Drew Tessier convinced me to perform standup comedy for the first time in his New York Queer Comedy Festival, and I very quickly started placing in and winning comedy competitions. In 2020, friends pushed me to post sketch comedy on TikTok, and my life changed overnight. I started getting TV auditions and appearances, collaborations with Paramount Pictures, the Indianapolis Colts, Lance Bass, you name it. Beyoncé even put me in her first TikTok ever! Which is still insane to me. Pinch me.
I’ve had a lot of twists and turns in my life. I’m also back in college right now getting dual degrees in History and French, because that’s another passion of mine outside of comedy.
You just rolled off a list of very impressive accomplishments, but because we are gay and basic we must at least briefly dissect “Beyoncé’s first TikTok ever!” What was that about!?
GURRRLLLL…. Picture it: Covid, 2022. Beyoncé Giselle Knowles Carter, hallowed be her name, has just come out with “Break My Soul.” Bop of bops, right? I posted a video of me dancing like an idiot to the song, and a few days later Parkwood Entertainment reached out asking for permission to use one of my videos, not specifying which. I can’t remember if I said yes or yaassss.
A couple of weeks later Beyoncé joined TikTok, and her first video was a montage of influencers dancing to “Break My Soul.” I’m the first white guy in the video, because diversity matters. My phone blew up and I gained 100,000 followers in one day. What’s hysterical to me is I was so broke that day, I literally needed a credit card to buy a bagel. I was eating it in Central Park when I found out. I about choked on my schmear.
Speaking of Covid, I understand that filming your season of Worst Cooks In America was disrupted by a positive test result. Besides that unfortunate conclusion, what was the Worst Cooks experience like for you?
Oh my God, I loved filming Worst Cooks so much. I got to make fun of myself on TV and take free cooking lessons from world-famous chefs. It was so silly and so informative at the same time. I also made lifelong friends that I still hang out with from that show.
And yeah, I had to leave the show because I got Covid from another cast member, who had to leave the previous week for the same reason. We were still in a Covid bubble at the time. And I was winning the show! I’m just happy I got to make [co-host / onscreen mentor] Anne Burrell laugh so much. Especially now that she’s gone. It really was such a special time.
She’s so deeply missed. Has your cooking gotten better, per chance?
No, my cooking has absolutely not improved. However, my knife skills have… thanks to Anne!
Regarding your standup, I’ve always imagined that it must be a challenge to figure out what material to put on social media, and what to save for the live audience.
It’s a challenge that keeps evolving, actually. When I first started social media, I was mostly doing sketch comedy and impressions. The trouble then was how to translate it to a comedy club where people expect standup. Now that I’m doing more live standup, the problem is figuring out which jokes to share online and which to save for the live shows. That’s why so many comedians only share their improvised crowd work online, and save their written material for live shows or a taping. It keeps people engaged and makes sure they’ll never be disappointed, online or live.
And that brings us to your new Monday weekly at Red Eye: “Comic Cabaret,” where you host an open stage for cabaret, standup and variety acts! Tell us more!
“Comic Cabaret” is a live comedy variety show featuring standup comics, Broadway stars, drag dancers, and musical comedians every week. I’ll be hosting, doing standup and musical comedy, and emceeing hilarious roundtables with the comedians. Then, it turns into a variety open mic for comedians, karaoke, musicians, poets… you name it! The lineup of guest stars is insane this whole summer; you’ve got to come out and see it. Mondays at 9!
What else is going on with or coming up for you?
Well, performing seven days a week in “Comic Cabaret” and Masquerade doesn’t leave much room for anything else… but I wouldn’t trade it for the world. To tell the truth, I’m really looking forward to being a hype man for other people in “Comic Cabaret!” I’ve got BGRE: Big Golden Retriever Energy. And I perform in a lot of different genres… so I figured, why limit the show? Why not perform different genres of comedy, and invite amazing performers from all walks of life? I get to host a free weekly comedy show with standup comics and Broadway stars. Pinch me. No really, pinch me. On the nipples. Harder, Jim, harder.
Lol, have you been reading my diary? Okay lastly: if you find a free minute in the coming months, what’s a show you’d like to see to NYC?
On Tuesdays, you’ll find me at my favorite drag show in town: Xana Dume at the Duplex. That girl has the legs of Giselle Bündchen and the feet of Ann Miller. I’d also love to sub out of Masquerade and experience it as an audience member. It’s so incredible.
Thanks, Charles!
Check Thotyssey’s calendar for Charles Osborne’s upcoming appearances, and follow him on Facebook, Instagram, TikTok, YouTube, LinkTree and his website.
Thotyssey 
Love this guy. Discovered him on the now-sadly-removed production of Oklahoma! he did in college which was proshot and put on local PBS, in Covid days when I was getting my theater fix online and have enjoyed seeing his name pop up around the internet since then.
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