Instagram Star Benito Skinner, Known for Kris Jenner Impression, Debuts 'Brand New' Music Video

Once upon a time, Benito Skinner, a.k.a. Benny Drama, was a high school football player in Boise, Idaho, who would listen to Britney Spears music on his way home from practice. Today, he’s a gay YouTube and Instagram star 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 with Overcompensating, 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.

From Riverdale to Keeping Up with the Kardashians, Skinner has parodied some of pop culture’s biggest fixtures in his videos, and now the comedian is taking on Thelma and Louise and Romy 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, the sponsor of The 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 for Kris Jenner and 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: When did you embrace your queer identity, and how do you think that that has impacted the way you resonate with your audience?
SKINNER: About three years ago, right around this time, I was still scared. There are a lot of systems that you have to fight against, and when you come out you have to [unlearn] a lot of the things that maybe you learned from school or from kids growing up. Just these little things about hating being gay, and hating your identity, and thinking that something is inherently wrong with you. So, it takes time. I don’t think you come out and you immediately feel amazing. For me, these videos are what helped me fully love my queer identity and find it as my strength as opposed to my weakness. And after about a year of making videos and sketches, I started to get comments from people who maybe weren’t out yet or who were just kind of figuring out their identity, saying that the videos made them want to explore that more and maybe not be so scared of putting themselves out there or of this queer identity. It’s been a process, but once you get to a place where you’re in love with it, I feel like it really is special.

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: If you could only perform as one character for the rest of your life, which character would you pick?
SKINNER: That’s so hard. Okay, I’m going to divvy it up. I’m going to do one celebrity and one character. Is that okay? Or is that cheating?
PEOPLE: Oh no, that’s great.
SKINNER: Okay, cool. So I love being Kris Jenner. She’s so much fun to be, and I have a lot of fun with that impersonation, and I feel like I’ve also injected like a different character into that. So it’s like Kris Jenner plus something else. And then I really love being Benita.
PEOPLE: What do you mean by “Kris Jenner plus something else”?
SKINNER: I’ve kind of given her this storyline. I was always reading that the devil works hard, but Kris Jenner works harder. I kind of turned her into a Satanic character. That to me is so fun because it’s obviously not her, so it’s like an impression of her plus this weird backstory I’ve now given her. She’s always fun to play. I love doing the makeup and the costumes for her. Anytime something happens with the Kardashians and I can make a video I get excited. And they make my life [unpredictable] because something always does happen.

PEOPLE: What’s the biggest Kardashian-Jenner development that has turned into a video?
SKINNER: One of my biggest was when the Jordyn Woods scandal broke. I did a whole bit on Kris Jenner leaving voicemails for Tristan Thompson and 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: I appreciate your affinity for Britney Spears, which is clear throughout the show.
SKINNER: She was the first album I bought. I remember I bought two Oops I Did It Again albums, because one had a scratch on it. I made my mom take me again and I purchased a second one. And I just remember watching the “Lucky” video and just waiting for it to be on TV. I think it’s probably my favorite song of all time. She was the first pop superstar I felt like I really idolized. I feel like a lot of queer people can kind of identify with these pop superstars that are owning their sexuality, and who they are on screen. You treat them like gods in a way. But yeah, I’ve always loved her, and even when I was in the closet, I couldn’t even help it. I would secretly listen to the whole Blackout album in my car on the way home from football practice — the strange juxtaposition of my life at that point.

PEOPLE: And now you’re a musician too. Tell me about your debut single “Brand New.”
SKINNER: I am in a full pop moment. “Brand New” was so much fun to make. I did one song with Benita, the character that I have as the lead singer in the song called “Frosty the F—boy.” It was so much fun. So when SVEDKA approached me, I had thought about doing a few songs for characters and was in the early stages. But they were super open about everything and approached it in a really fun way. They wanted me to just do my thing, and their whole campaign is “Bring Your Own Spirit.” I immediately was drawn to Benita being the lead and then having two of my other female characters be taught by her to get rid of these things that you’re supposed to do and just own your s—, let loose and be a bad bitch. In the video, we wanted to reference as many female empowerment stories as possible. So we chose Thelma and LouiseRomy and Michele’s High School ReunionCoyote Ugly, Britney’s “Toxic,” and then “Diamonds Are a Girl’s Best Friend.” So yeah, that’s like the essence of the video. We want these very bad bitch moments, and we kind of jam-packed them into one minute in a traditionally masculine setting like a pub. Kudos to director Lula Hires for that one.

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 to Riverdale. 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.”

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