It's always a tense part in an interview, the moment where the journalist finally has to ask the question they've been dreading: How does an actor feel about their most famous role, the one from years ago, the one that defined them?
Many celebrities balk at discussing their most well-known character, wanting distance from their earlier work, even if it's beloved. But Jonathan Bennett isn't most celebrities. If this were a holiday rom-com, he would be the actor shooting on location in a small town, who charms and delights the at-first suspicious local residents with his down-to-earth openness and genuine love for the holidays.
Bennett came from a small town himself, and this season he's back to a fictional one for the new Hallmark Channel Christmas film "The Holiday Sitter." It's a long journey from "Mean Girls," the 2004 Lindsay Lohan-fronted comedy classic that gave Bennett his first major role and made fetch happen. In another sense, it's no distance at all.
Born and raised in a small town in Ohio (as was this writer, a fact we reminisce about), Bennett left for New York and was cast in the soap opera "All My Children." Stints in "Smallville," and that rite of passage for many New York actors: "Law & Order: Special Victims Unit" followed, as did an appearance on the first season of "Veronica Mars." But it was "Mean Girls" that gave Bennett his big break. Bennett played Aaron Samuels in the Tina Fey film, the dreamy love interest for Lohan's character. He sits in front of her in math class, asking to borrow a pencil and memorably inquiring what day it is.
During an interview with Salon, Bennett had nothing but good things to say about "Mean Girls" and its stars. "It's not a regular movie. It's part of people's lives. They speak it, they talk it and they have parties for it. They dress up like it for Halloween. The lines in 'Mean Girls' are in people's everyday vocabulary now."
As far as his famous role, "You're not going to run away from it," Bennett said. "So, I embraced it." In 2018, he launched a cookbook, "The Burn Cookbook: An Unofficial Unauthorized Cookbook for Mean Girls Fans" because he wanted "to celebrate and pay my homage to all the fans who help make us who we are."
Aaron Samuels was that rare teen heartthrob who was sweet as well as swoopy-haired, who had empathy, helping his mom out at home during most of his free time, as well as charm, attributes which may at least partially explain the character's staying power. But a big part of the character's endurance is Bennett himself, his performance of complex and quiet kindness.
Bennett said, "I owe my entire life, my entire career" to the film. "Everything about who I am today I owe to Tina Fey, Lorne Michaels and Lindsay Lohan."
The Holiday Sitter (Hallmark Media/Craig Minielly)Who Bennett is today includes being in front of Hallmark's first-ever holiday project that centers an LGBTQI storyline. In "The Holiday Sitter," Bennett plays Sam, a gay man who reluctantly bails on his luxurious holiday plans to babysit at the last minute for his sister's kids. The sister's helpful neighbor (George Krissa) who happens to be gorgeous, gay and interested in adopting to start his own family, causes Sam to reconsider what he's always believed: that marriage and children are not for him.
"They're not just regular movies, they're movies that make people feel like they have a sense of family."
Bennett came out on the set of "Mean Girls," as did fellow actor Daniel Franzese, who played Damien. Though it was a private coming out at the time, a public one followed in 2017. In March 2022, Bennett married actor and television host Jaymes Vaughan.
It's been a long Christmas movie journey for Bennett, who has appeared in many of the popular films. When Vaughan proposed, Bennett was starring in "The Christmas House," the first Hallmark Channel holiday film with a gay character in a featured yet supporting role. But Bennett not only stars in "The Holiday Sitter," he wrote it, as well as executive produced. The film's director, Ali Liebert, also identifies as queer.
"Growing up, I never saw a Christmas movie that had a love that looked like mine, or a relationship that was the kind of relationship I wanted to have with someone," Bennett said. "So, the holidays always looked different on TV to me."
Bennett said after doing his first holiday film and getting to interact with fans, he realized these were special stories, important to many viewers as more than just movies. "These movies mean so much to so many people during the holidays when people don't have families to go home to, or maybe they've lost loved ones," he said.
"It's a way for people to connect with these characters on camera. And the Hallmark Channel actors become the chosen family of so many people around the country. It brings warmth and happiness to them during the holidays. Once you do one [holiday movie], you kind of get close, and you can't stop making them because they're so much fun. Because they're not just regular movies, they're movies that make people feel like they have a sense of family during the holiday."
The Holiday Sitter (Hallmark Media/Craig Minielly)
"You can have your own chosen family. Christmas becomes magical again."
The idea of chosen family is essential to "The Holiday Sitter," where several characters are expanding their family or hope to through adoption. As Bennett says, "family comes in so many different sizes and shapes. And it doesn't matter what your family looks like, as long as it's filled with love."
Chosen family is also often a key part of the lives of queer people, who may have been rejected by their biological families or feel more at home and like their true selves among understanding friends. "The holidays aren't always perfect for our community," Bennett admits, which is partially what led him and his husband to co-own an LGBTQI travel company, OUTbound. The company is leading a tour of Christmas markets in Switzerland, France and Germany that Bennett and Vaughan plan to attend this year, before Bennett returns to New York to host the Times Square New Year's Eve.
Bennett knows it can be especially hard for queer youth around the holidays. His advice to any young person who might be struggling? "It gets better. And when you're old enough, you can have your own chosen family. Christmas becomes magical again. I promise because I've been there."
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His career may have been launched as the dream guy on a teen flick, but Bennett's work has included not just the stuff holiday dreams are made of, but more dramatic roles as well. He was captivating in the 2019 Hilary Duff-led film "The Haunting of Sharon Tate," a film he seems surprised I have seen. But Bennett as Jay Sebring brings light to the complicated, real-life role, as well as his signature empathy as an actor.
His process is the same, whether filling the shoes of a sweet romantic lead or a tragic and complex figure from history. He does his homework, reading up on the role, "[I] think about what he would do in that moment. And then stand on my mark."
What happens when the dream guy grows up? He never stops dreaming, and he hopes we can make some dreams a reality along with him. Bennett made "The Holiday Sitter" for all audiences, describing it as "just a story about Christmas . . . It just happened to have two men as the leads, versus a man and a woman." But he hopes queer viewers, the community close to his heart, support it as well.
"With 'The Holiday Sitter' I can only imagine what a 16-year-old me would feel when he saw this movie. A love that looks like his represented on camera."
"The Holiday Sitter" premieres Sunday, Dec. 11 at 8 p.m. on The Hallmark Channel. Watch a trailer via YouTube below
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