trick or treat

Benito Skinner and Terrence O’Connor On How To Make The Perfect Couple’s Halloween Costume

Benito Skinner as Marilyn Monroe and Terrence O’Connor as Jackie Kennedy. Dresses by Christopher Palu.


You’d be hard-pressed to find anyone who does Halloween quite like Benito Skinner –  more famously known as Benny Drama, the comedic, YouTube sensation– and his boyfriend, the director Terry O’Connor. Before the two even met, there was an almost cosmic correlation to their costume decisions (In their senior year of high school, Skinner was the Pope and O’Connor a nun.) Now, as a couple, the two have tackled outfits from mega-celebrities Kendall and Kylie Jenner to ice cream moguls like Ben and Jerry, and regularly push the envelope on how to properly curate a Halloween costume. On the eve of Halloween 2021, the two spoke about their decision to dress up as Jackie Kennedy and Marilyn Monroe this year, and how Halloween as a holiday has proved to be a pivotal factor in accepting their respective queer identities. — JACKSON WALD






SKINNER: You’ve definitely heard this many times, but Halloween was always very important to me. It was the only time of the year I could tiptoe into being myself without getting caught in the closet. I distinctly remember fifth grade was one of the first times I went really hard for Halloween. I went as Willy Wonka. I had the big Johnny Depp white glasses and a bob [wig]. I was going to go into school and my mom was like “Are you sure?,” and I was like “Bitch yes I’m sure. I’m about to teach some lessons.” 

I felt so confident that whole day and I always tell people: the first time you go really hard you’ll never go back, because you realize how fun Halloween can be when you allow yourself to give the drama.

O’CONNOR: It’s so funny because I had the opposite response to [Halloween] growing up. I was so scared of my costumes like marking me as gay, and I didn’t know how to make good straight references. So as a kid, I would always go as a vampire because I was like “I’ve done this once. It went over pretty well. I know how it goes.” And then I just stuck with that. It wasn’t until college that I became really into doing Halloween.

SKINNER: Do you think it had something to do with the fact that you were at an all-boys school? I felt comfortable because all my girls were also going hard, and I would help them with their costumes.

O’CONNOR: Period. I also didn’t have friends in high school.

SKINNER: [Laughs] I didn’t really either.

O’CONNOR: I never really had anyone to go trick or treating with, so I would always go with my little sister who is four years younger than me. And one year I went as my same old Dracula. It was just a little too late in my career — I was 12 years old. That was when kids started staying home or hanging out with their friends. And I went with Claire who was eight years old and who dressed up as a princess. We knocked on the door and this girl, Hope Hanley, who was my grade, opened it, and she was like “Terry?

That was really scarring for me. Once I got to college and actually had friends, I felt more comfortable.  But after that, I was like “Nope, this isn’t for me.”

SKINNER: I felt really lucky when we met because our first Halloween didn’t go that hard, but I could sense that there was a spirit within you.

O’CONNOR: Our first party, Ben went as the Genie from Aladdin with full blue makeup covering his entire body. This was a period in our relationship where I was just starting to meet his family and friends. Honestly [it was] the only time in my life that I did a hot-boy costume of a werewolf, which is just wearing a plaid shirt and having some scruff.

SKINNER: You were snatched. 


O’CONNOR: It was an interesting time in your life because you were beginning to really take the videos that you were making seriously. At the time, you were watching a lot of makeup tutorials to try to learn how to do Kim Kardashian makeup or things like that. The love for makeup spilled over into the Halloween costumes, and you and I both were feeling ourselves so hard that night.

SKINNER: Halloween helped me express my work and drive that forward because I was starting to bring out wigs and makeup and be characters who were women and men, and I was, for the first time, fully accepting my queer identity. I also felt like I could make stuff that was more campy and true to what I wanted to make.

In a lot of my work, you see someone starting to love the fact that I am gay and love all that my creativity wants to do, and the things I have wanted to do for so long. I’m sure that seven-year-old me would have had the time of his life being Britney Spears for Halloween, but unfortunately, he couldn’t be. So I get to do that now. Halloween just drives me forward in that way of true creative expression with no boundaries. 

O’CONNOR:  Ben and I came out only a few months before we met each other, and then we immediately entered into our relationship. We were on a similar timeline of becoming ingrained in gay culture, learning about it, making gay friends, and loving ourselves as gay men.

I remember very vividly this one dinner that we went to very early on, when we first moved to New York. This other gay guy was there, and he said faggot. We were both clutching our pearls like, “Oh my God, that’s horrifying. Why would he ever say that.”  And I think that’s a classic journey of recently-out gay men. We had a long way to go with our own comfort around all facets of what it means to be a gay man. Our eventual embrace of Halloween has very much paralleled that journey of self-acceptance and no fear.

SKINNER: There’s power in taking back words like faggot and stepping out on Halloween and feeling confident, and realizing that it can also inspire people around you to go off and have that moment for themselves. I do think that’s really special. I love doing friend’s makeup on Halloween; Terry and I love to direct the people around us. We’re lucky that the friends around us will go along with our costumes, but I also feel like they are very excited about it now.

The year I did Lizzie McGuire, I met this designer Christopher Palu. He DM’d me, and I was like “I’m looking for a costume designer. I have a very niche idea for a costume.” And he made it for me.  It was this very insane moment because I got to live out my fantasy and it also was this special relationship with this gay designer. I’ve been making all my costumes with him ever since, and he’s been making Terry’s as well.

So the next year I knew that I wanted to do something that felt bigger than the Lizzie moment, and also felt more current.  So Terry and I were watching Met Gala coverage, and we saw Kendall and Kylie walk out, and we were just like “Oh bitch, that’s what we’re doing. 100%.”

I was Kylie, and I’m in a strapless dress — there’s nothing worse on earth. My dress weighed like 100 fucking pounds. And Terry’s just in his glitzy, flapper Versace recreation just dancing around having drinks.

O’CONNOR:  I lost feeling in my head because I have Neanderthal eyebrows and so, in order to try to look anything like Kendall Jenner, they had to tape them so far fucking back that my whole head went completely numb and I was delirious.

We met Kendall recently, and we were telling her about it and it was this terrifying moment where she was like “Oh my God, I want to see.” It was that moment when you’re like “Okay, let me find this picture” and you’re scrolling forever and the wi-fi is not working and the photos not loading, and an eternity has gone by. I was like “Oh God, this is not gonna end well.”

But she was like “Oh my God, you look like me!”

SKINNER: Terry tells this story to literally anyone who will listen.

With Kendall and Kylie we knew we were going out on the town, so it felt really fun to have a very grand moment for that. But the next year it was like “Okay we’ll scale it down,” which kind of leads into why we chose Jackie [Kennedy] and Marilyn [Monroe] this year.

I had done childhood nostalgia moments — I’ve done Lana [Del Ray] and [Lady] Gaga like five times — and instead of going for something that was super a part of popular culture, I wanted to go more historical. I’ve always wanted to be Marilyn and Terry’s always wanted to be Jackie and those characters are so separate, but still in the same storylines. I am such a Marilyn and Terry’s such a Jackie, and it felt so funny for us to have these power women link up. The second we had the makeup and costumes on for this shoot, we were like “Oh, this is it”. I think it’s my favorite that we’ve ever done by far.

O’CONNOR: Ben as a Hollywood bimbo and me as an uptight, east coast, original horse girl leans pretty nicely into our backgrounds.

It seems like every year, Halloween becomes more and more of a cultural moment. I think it’s pretty closely tied with Instagram and the rest of the Internet. Maybe it started with people like Heidi Klum, having those massive red carpet entrances at her party and every year, she was going crazier and crazier. And then with the Internet, I felt like the rest of the celebrity world was starting to get into prosthetics and really drawn out Halloween costumes.  And with that came a lot of ‘who’s making the funniest cultural reference? What’s funny, timely, hot?’

MACIAS: What do you think they would each think of your costume?

SKINNER: I think Marilyn would like it. She would comment on the size of the boobs I have, though. She’d be like, “You’re absurd.” In my heart, I think she would laugh. I think Jackie would be like “Why am I with Marilyn. Like, what the fuck.”

O’CONNOR: I think Jackie would be horrified. But also I think that’s the vibe of that entire generation.

SKINNER: Don’t you agree that Marilyn would be like “That’s cute.”

O’CONNOR: I don’t know. Were people having a lot of fun back then?

SKINNER: I think Marilyn was. At times. I feel like Hollywood was a lot more fun than Washington.

MACIAS: Do you realize that by doing these extravagant feminine costumes, you’re making it a little bit easier for other kids that are not in LA, Chicago and New York to take this step? Does that ever weigh on you? 

 SKINNER: I always say that I hope people leave my work feeling a little bit more comfortable being dramatic and being over the top. There are so many people who tell you to reign it in, not speak too loudly or don’t want you to be the center of attention. I hope that in some of the work that I’ve done with Terry, especially some of the photo shoots that we’ve done together, that people feel a little bit more comfortable putting on a full platinum wig and red lipstick.

O’CONNOR: It weighs on us every day. It’s the goal and the purpose. Someone once asked me, “How many lives do you think you live?” And I was gonna say “I feel like I’ve lived five different versions of myself,” but, the version I am today is finally back to my five-year-old self that was playing barbies with his sister, and unaware of the cruel things people would say about me or to me.

The goal for both me and Ben in our personal lives is doing what makes us feel good about ourselves, and hopefully trying to multiply that happiness amongst others, who can either participate or are just watching along. 

Our relationship wasn’t always like this. Especially at the start, before Ben’s career was beginning to take off, and we were doing these things on a smaller scale, with tight budgets and not many eyes on it, there were some people being like “Maybe you should do fewer wigs” or “Do you really need to do drag all the time?” and we were like “No.”

SKINNER: It was really important to me. There is something beautiful when you feel really confident in who you are, that you don’t need an outside opinion and you don’t need validation from people that have made you feel small.

MACIAS: What are your actual plans for Halloween?

SKINNER: I’m throwing a party with Spotify and my co-host of Obsessed Mary Beth Barone in Hollywood. I am wearing a different costume for that because I can’t wear the same costume twice. That’ll be a fun little surprise; it’s more based in pop culture.

The next night Terry and I will go out as Jackie and Marilyn. We’re just going to take the town. We don’t necessarily need a party. We’ve contemplated renting an old car and just driving around LA.

O’CONNOR: Well, we have a friend’s party… 

SKINNER: We do have a friend’s party,  but I have this dream of us driving down Sunset [Boulevard] and Maryland and Jackie just running away together. Jackie’s ripping cigs and Marilyn’s eating a burger. I think that’ll be my dream come true.

O’CONNOR: We might just ride off into the sunset and not look back.


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Creative Direction by Benito Skinner and Terrence O’Connor

Photograpger Assistant: Emily Malinowski
Hair: Castillo
Marilyn Wig: Wigs & Grace
Marilyn Make-Up: Lilly Keys
Jackie Make-Up: Benito Skinner @bennydrama7