Photo: Craig Barritt/Getty

Benito Skinner

Once upon a time, Benito Skinner, a.k.a. Benny Drama, was a high school football player in Boise, Idaho, who would listen toBritney Spearsmusic on his way home from practice. Today, he’s a gayYouTubeandInstagramstar and comedian based in Brooklyn, New York, whose impressions and sketches have garnered over 50 million views on social media.

Skinner, 25, embraces his transformation into his authentic self withOvercompensating, a hilarious live show mixing comedy, music and drag that he debuted at New York City’s famed Carolines on Broadway in June.

After opening the show with a clip of high-school Skinner making moves at a football game, he ascends the stage as Spears’ “Lucky” blares through the auditorium. The audience howls and claps — a full-circle moment in an unconventional career that took off after he studied film at Georgetown University and put the skills he learned to work online.

FromRiverdaletoKeeping Up with the Kardashians, Skinner has parodied some of pop culture’s biggest fixtures in his videos, and now the comedian is taking onThelma and LouiseandRomy and Michele. In the music video for his single “Brand New,” Skinner rocks a blonde wig and kicks up his heels on a bartop while singing about the joys of SVEDKA Rosé vodka, which sponsored the Pride show in N.Y.C. onThe Overcompensating Tour. (See ticket information here.) An ode to the ubiquitous love of rosé, the clip is also a sweet taste of the humor Skinner brings to his shows.

Below, Skinner talks with PEOPLE about how accepting his queer identity led to creative and viral success, his love forKris Jennerand more.

PEOPLE: When you look back at your genesis, how did you go from football player to YouTube star to live performer? Was any of this planned?SKINNER:I wish I could say there was more planning a part of it. In a lot of ways, once I came out then I was finally being myself and being authentic. There was no way I wasn’t going to be a performer or an actor because it just started happening so quickly, as far as my creations or how much I wanted to put out there. Once I came out, it just poured out of me in the way that it did when I was a kid before I went to school and started to like hide my queer identity. The internet has this amazing thing — sometimes it can be scary, but once it goes, it goes. I started posting videos and people responded, and it made me feel so good doing it. I could see that it was making people feel better, or maybe turn a s—ty day into a good day.

PEOPLE: How many characters do you have? Have you ever counted them up?SKINNER:Oh my God, I think I had to count them up once. If it’s just fully original characters I think I have around 12. And then if it’s impressions, I’m in the 40s, I believe.

PEOPLE: What’s the biggest Kardashian-Jenner development that has turned into a video?SKINNER:One of my biggest was when theJordyn Woodsscandal broke. I did a whole bit onKris Jennerleaving voicemails forTristan Thompsonand coming to get him. That was so fun. And I made that within 24 hours of the news breaking, which was just exciting to immediately make something, put it out there and be a part of this conversation, which I think is kind of the beauty of the internet. But yeah, that one did well and was so, so fun to make. Yeah.

PEOPLE: What about your favorite original character?SKINNER:Original characters would definitely have to be Benita, who’s my feminist southern belle. I really have so much fun being her. I feel like we align as far as our morals, and you know, as far as other characters I don’t really feel are necessarily a part of me, but she definitely feels like she’s a part of me. I love being her. She has this great empowering that bitch energy that I love.

PEOPLE: Your live show looked like a rich culmination of everything you’ve ever done — jokes, impersonations, drag, music moments. Can you even define it as stand-up comedy?SKINNER:Carolines had reached out to me a while ago and said, “Do you have a live show? You know, we’re super interested in seeing what you could bring to the table.” And I had some ideas and I had some stand-up bits in my head. But I knew that people were going to show up wanting characters, and so I wanted to deliver that but I also didn’t want to necessarily have to change 30 times. When approaching it I was just like, “Okay, I want to make videos that wouldn’t necessarily work in just an Instagram setting or posting them just to the internet.” I wanted videos that I could interact with, that were a part of the show. It just evolved over time. I did a lot of open mics, and I tested the stand-up. What was fun about the stand-up portion of the show is that it’s more personal, whereas a lot of my videos aren’t necessarily personal because they’re just impressions or sketches.It was fun to talk about my experience coming out and some of the ways I was aggressively overcompensating to remain in the closet. And yeah, the show is very much a variety show with stand-up, and singing, and the sketches. So it’s so much fun to perform still. Even though I’ve done it probably 30 times, I still love doing it and the audiences have been so much fun.

PEOPLE: How would you describe your brand of humor to someone who hasn’t seen any of your videos yet or is perhaps seeing a clip for the first time?SKINNER:I would say very self-deprecating of myself and also millennials in general, and probably Gen Z as well. You know, I really love to point out things in pop culture and social media and this age of the internet, some of the strange things that we do. I hope that my comedy pokes fun but also comes from a place of love, usually. I never do an impression of someone that I don’t really respect.

PEOPLE: What are your favorite everyday life things to do?SKINNER:My favorite thing in the world is just going to a movie with either friends or family and getting a frozen Coke slushy and popcorn. If I do that I’m like in heaven. My boyfriend is going to be like, “Okay, bitch.”

PEOPLE: What’s the most annoying thing in the world?SKINNER:I really don’t like when people just have a naturally bad attitude, whether that be being rude to a barista, or just saying something s—ty to somebody. Anybody that wants to take the light out of the room, or of the moment or make someone’s life a little bit harder. And oh my God, if you’re on a date with someone and they’re rude to the waiter, it’s like, I’m out.

PEOPLE: And now, to get a little scandalous, what’s a secret no one knows about you?SKINNER:Oh my God, a secret? I don’t have any. I’m gay. No, let me see. I’m pretty secretly addicted toRiverdale. I feel like I watch that at night all the time. Even my boyfriend will just be like, “All right. I think I think we’re done for the day.”

source: people.com