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Jonathan Bennett’s Wild Journey From ‘Mean Girls’ to Broadway’s ‘Spamalot’

Photo Illustration by Luis G. Rendon/The Daily Beast/Getty/Food Network/Hallmark/Andy Henderson
Photo Illustration by Luis G. Rendon/The Daily Beast/Getty/Food Network/Hallmark/Andy Henderson

There are certain dates that are heavily associated with individual people. Presidents’ Day, of course, is tied to George Washington and Abraham Lincoln, whose birthdays are being celebrated. Christmas Day gets Santa Claus—and, uh, Jesus. And then there’s Oct. 3, a seemingly innocuous date that has become hallowed among pop culture fans. That is the day that everyone thinks of actor Jonathan Bennett.

Bennett starred as high-school heartthrob Aaron Samuels in Tina Fey’s 2004 comedy hit Mean Girls. A throwaway line from the film in which Lindsay Lohan’s character, Cady, who has a crush on Aaron, asks him the date. Aaron smiles and says “October 3.” Now, every Oct. 3, we celebrate Mean Girls Day—and fondly think of Bennett in that scene.

Of course, there are plenty of reasons to think of Bennett on the other days of the year. The actor is a fixture on the Food Network, where he’s hosted baking competitions Halloween Wars and Cake Wars, and the Hallmark channel, where he starred in the network’s first Christmas romance featuring a gay couple, 2022’s The Holiday Sitter. Mean Girls is back in the zeitgeist, with a new movie musical that was released last month, though, as Bennett tells me, “I don’t think Mean Girls ever left the conversation.”

Then there’s the dream he’s been living eight times a week: his Broadway debut playing Sir Robin in the current revival production of Spamalot, replacing Michael Urie, who originated the role. As the daffy, somewhat dim knight who is bashfully obsessed with musical theater, Bennett gets to put on a wig of long, blonde, curly hair, and perform Act 2’s show-stopping production number “You Won’t Succeed on Broadway,” a cheeky homage to the glitz and glam and razzle-dazzle of the Great White Way’s most iconic shows. (A recreation of the Fiddler on the Roof bottle dance, for example, typically garners mid-song applause.)

Jonathan Bennett takes a bow in ‘Spamalot’

Jonathan Bennett in Spamalot

Andy Henderson

“The funny thing about the character of Sir Robin is that he’s basically Jonathan Bennett,” Bennett says, speaking on Zoom before a recent performance. “He wants to just dress up and dance. I get that great monologue where I get to talk about how much of a special place Broadway is and how it’s filled with very special people. I get to do the whole monologue about being on Broadway on Broadway. There’s no better moment of your life than standing center stage, singing a song about how amazing it is to be on Broadway, while you’re at the St. James Theatre on Broadway.”

I barely get the question out—”Have you been a musical theater person your whole life?”—before Bennett starts laughing. “Have I been a musical…? YES!” he says, emphatically shouting the “yes.” “I’ve wanted to be on Broadway since I was 5 years old. I am the biggest musical theater junkie in the world.”

After graduating high school, Bennett began studying at Otterbein University in Ohio, before moving to New York to start auditioning for theater. In 2001, when he was 20 years old, he got his break on the ABC soap opera All My Children. Because he was making a name for himself on TV, his agents encouraged him to move to Los Angeles. He quickly booked Mean Girls, “and then I just kind of stayed in L.A. and kept working in TV and film for 20 years,” he says. “But I’ve always had that dream of, ‘But I want to do live musical theater. I want to be on Broadway.’” It’s the first of several times in our conversation that Bennett refers to his role in Spamalot as a dream come true.

Broadway is another distinctive niche of pop culture that Bennett has now infiltrated, which means encountering another group of fans to interact with. One imagines, based on their respective popularity, that the Hallmark fans and Mean Girls fans are passionate people. How do Broadway fans compare?

“What’s so funny is that the Mean Girls fans and the Hallmark fans and the Food Network fans are Broadway fans,” Bennett says, smiling. “If you think about it, Mean Girls is one of the gayest movies of all time.”

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As someone who’s spent the last 20 years incessantly quoting the movie with his gay friends, I can corroborate Bennett’s thesis. The character of Damian (Daniel Franzese), who was “almost too gay to function,” was a formative queer character for millennials on their own journeys with their sexuality. But back when Bennett was making the film, he had no idea that it would become so indelible, or that the LGBT+ community would latch onto it the way they did.

“I was still living in fear in the closet, of being found out that I was gay,” he says. “It was 2003. It was a different time in Hollywood, where leading men couldn’t be gay. That just wasn’t an option. So shooting it, we were just a bunch of kids making a movie that the girl from Saturday Night Live wrote that was hilarious. It was more of that than anything.”

It’s a fun piece of trivia that all three of Mean Girls’ leading men—Bennett, Franzese, and Rajiv Surendra, who played Mathlete rapper Kevin—are gay and have, since the movie premiered, come out publicly. A cute layer to that: Bennett and Franzese came out to each other during filming.

Bennett publicly confirmed that he was gay in 2017. In 2022, he married former Amazing Race contestant Jaymes Vaughn. The two were the first gay couple to appear on the cover of the wedding magazine The Knot, and their Instagrams are a treasure trove of content documenting their life and relationship. Because of his role in the The Holiday Sitter, a landmark moment when it comes to LGBT+ inclusivity, Bennett’s even been dubbed the “Gay King of Christmas.”

It’s been cathartic and profound for Bennett to, because of the new Mean Girls movie and the 20-year anniversary of the original, be able to talk about his experience making that film from a space of security in who he is and in his sexuality.

“When people say that being your authentic self and living your truth is the most powerful thing, it’s true. I wouldn’t be here without living my truth and showing the world who I am,” he says. “Because when you do that, then people can actually see you and they can see who you are. They can connect with you as a human being playing that character versus an actor who has his guard up because he’s afraid that he might make a gesture, or talk too high in his voice and people might think he’s gay, so he’s scared. Because all you’re thinking about when you’re acting is, ‘Oh, God, don’t let them know that I’m gay.’”

Lindsay Lohan looks at Jonathan Bennett in a classroom in a still from ‘Mean Girls’

Lindsay Lohan and Jonathan Bennett in Mean Girls

CBS Photo Archive via Getty Images

“That was part of my life for 10 years, in every role, in every audition,” he adds. “Then, 20 years [after Mean Girls], to be on Broadway singing one of the biggest gay numbers there is, doing tap dances on a Broadway stage, is just completely freeing. When you live your authentic truth, you're completely free, and the audience feels it.”

Spamalot isn’t just a gig. It’s been an outlet for Bennett to work through all the pain he’s felt throughout his career because he felt that he needed to hide who he really was.

“I almost feel like doing this show is therapy for the scars and the wounds of living in the closet and living a life that you were told you’re supposed to live,” he says. “That comes with a lot of scar tissue. Being able to be my big, gay self on a Broadway stage has kind of helped to heal those 10 years of your life where you couldn’t be your true self.”

Being out and in the public eye can often carry with it a social responsibility that is thrust on queer celebrities, whether or not they desire to be an advocate or mouthpiece for issues facing the community. In recent years, Bennett has taken that opportunity seriously. One of the reasons he and his husband are so active on Instagram is because they see something powerful and potentially impactful about that visibility.

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“It isn’t because we need the attention of people seeing our relationship,” he says. “That’s not something we need or care about. What we care about is that when we were young and in our formative years, we didn’t see any couples or love that looked like ours being displayed anywhere. And so it’s important for us to share who we are and what our relationship looks like with people, because you never know who’s going to see it and feel less scared or less alone.”

Bennett is also aware of the unique position he’s in as a gay man who hosts TV series on the Food Network and stars in Hallmark Channel romances, and who is never shy about who he is. These are networks with a major reach across the country, and which count conservative viewers among their audience. While Hallmark has made great strides in diversity and inclusivity, for example, it did take until 2022 for a same-sex couple to be featured in a Christmas film.

“My favorite thing is to tell queer stories in conservative spaces, because I think it’s something that needs to be done and done every single day,” Bennett says. “I always say that the people that watch RuPaul’s Drag Race, they’re already on our side. We’ve already got them. It’s the people that might not have many people in their life that are gay that they know about, or might not be around gay relationships, or might not see what love looks like between two men in a beautiful, heartfelt relationship [that we need to reach].”

Jonathan Bennett and George Krissa hold hands in a still from ‘The Holiday Sitter’

Jonathan Bennett and George Krissa in The Holiday Sitter

Hallmark Channel

“So to be able to go on places like Food Network and be my complete self, my just spastic, big, old, gay self on that network and make everyone laugh, and to be on Hallmark and tell these amazing love stories about LGBTQ+ characters, it is such a powerful thing,” he adds. “You’re pulling back the curtain and showing people that an audience that might not normally have a lot of gay people in their life that they’re aware of.”

It isn’t lost on Bennett that all of this opportunity—the Hallmark movies, being a role model for queer youth, being on Broadway—has come because a movie he starred in 20 years ago has remained such a major part of the zeitgeist. Yes, there’s a new musical movie version of Mean Girls you can watch now, and that’s great and welcome. But nothing will ever be as fetch or as grool and the original phenomenon.

“You remember where you were the first time you saw the first viewing,” he says. “Not many people can say that about different movies. Mean Girls is just glued in people’s brains. But it’s also great to be reinvented, because times are changing. You always have to keep changing. So while I think this new version reinventing it is lovely and awesome and a great idea, the original will just always be the one that’s glued into people’s brains.”

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