Known as "Hallmark Royalty" for his extensive contributions to the network, Jonathan Bennett is kicking off 2025 in a big way.
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New Year,
Same King:
Jonathan Bennett’s
Reign Continues

You’ve had an impressive career acting, producing, hosting, and even starring on Broadway. What has been the key to maintaining such longevity and versatility in the entertainment industry?

You don’t sleep, and you hustle harder than you ever thought possible. Everything I’ve achieved throughout my career wasn’t handed to me. It’s all stuff I had to fight for. Whether it’s hosting Halloween Wars, creating the TV show Finding Mr. Christmas, or doing Hallmark movies, including the first Hallmark trilogy based on men [The Groomsmen], I had to put in the work to make it happen. The reality is, if you don't put in the work, someone else will. The past year has been a year of no sleep and nonstop hustle, but I’m extremely grateful and proud of myself.

Broadway has been a lifelong dream for you, and last year you starred in Spamalot on Broadway. Can you share about how it felt to experience that dream?

Yeah, absolutely. Being on Broadway has been a dream of mine since I was five years old, but then I started doing movies and TV shows, so it kind of fell on the back burner. At one point, I started thinking, “Maybe that’s not going to happen for me. Maybe it’s just not my path.” But that longing and itch to be on Broadway never really went away. Then, out of the blue, I got a call from my manager. He said, “You’re not going to believe what I’m about to ask you—do you want to be in Spamalot on Broadway?” I was stunned. It was the most surreal, incredible moment. Stepping into a show as big and fast-paced as Spamalot was like a rocket ship. From the moment the curtain rises, it takes off to the moon and doesn’t stop for two hours. And to not only be on Broadway but to do it with that show, surrounded by an amazing cast of Broadway legends, was beyond anything I could’ve dreamed. There’s nothing better—nothing.


You executive produced and starred in The Holiday Sitter which served as Hallmark’s first LGBTQ+ romantic comedy. Can you share about how you brought this project to life and what it meant to you personally and professionally?

My philosophy has always been, “If you don’t see it, it’s your job to be it.” When those stories weren’t being told, I felt it was my responsibility to create those stories and tell them. Hallmark has been extremely supportive and absolutely committed to making sure the stories they tell reflect the people who watch their movies. So many LGBTQ+ viewers love Hallmark movies, and so we need to make sure that their stories are being told along with all the other stories. I think we’ve also done a fantastic job of making sure the stories reflect the human element of the characters versus the fact that they’re queer. Representation matters, and you don’t realize how much it matters until you see yourself in a movie with a love story that looks like yours on a network that's based around love.

It’s been an honour and a privilege to create something like this, but I also feel it’s a responsibility—one I’m proud to take on.

At the end of 2024, you had an incredible lineup of releases: Season’s Greetings from Cherry Lane, the reality competition series Finding Mr. Christmas, and The Groomsmen, the latest installment in your Hallmark trilogy. Tell us about these projects.

The Groomsmen is such an exciting project because it’s part of a trilogy I created with Tyler Hynes. It’s the first time Hallmark has told a love story from the male point of view, so it’s basically like The Hangover for Hallmark. It’s about three best friends navigating love while keeping each other honest, calling each other out when needed, and having those real, funny, and heartfelt moments you’d expect from a group of guys. I think it’s a really interesting take on a romantic comedy, so I’m incredibly proud of it.



Finding Mr. Christmas is a show that I created, and it is America's search for the next Hallmark holiday movie star. So it's a little bit RuPaul’s Drag Race meets America’s Next Top Model meets Big Brother, and it’s Hallmark’s first unscripted reality competition series. Ten guys move into a Hallmark Christmas house and compete in challenges inspired by classic Hallmark movie tropes, like the meet-cute, the mistletoe kiss, etc.—all the things you have to do to be a Hallmark leading man. One by one, they’re eliminated until the final guy is crowned Mr. Christmas. The winner gets a lead role in an actual Hallmark movie, which airs the following week. It’s available on Hallmark+ in the USA and W in Canada. I think it’s the best show I’ve worked on in my 26-year career.

And then there’s Season’s Greetings from Cherry Lane, which rounds out the lineup perfectly. Streaming December 5 on Hallmark Plus, this project takes last year’s Cherry Lane, a fan-favourite holiday movie, and expands its universe in an entirely fresh way. The original movie revolves around Christmas Eve in one house, showcasing the holiday through two families, 20 years apart. Now, we’re turning it into a larger, interconnected world—think of it as the Avengers of Christmas stories. Each storyline from the original is branching out into its own movie, with new narratives woven in. It’s a web of Christmas magic, all centred on the same house on Cherry Lane. 2024 was such a rewarding year, and I can’t wait for everyone to experience these incredible projects!


You have a strong presence in both scripted and unscripted work. What do you enjoy the most about each format?

I love storytelling, whether it's in scripted series or movies. In scripted work, you're creating the story from the ground up. But in reality TV, the stories are already out there, and you're uncovering them with the contestants, following their journey. So, one is all about creation, while the other is about discovery. It's a different mindset for each, and I honestly love them equally. I can't pick a favourite—they’re both like my children, in a way, each special for different reasons.


You played Aaron Samuels in the iconic movie Mean Girls. With the movie being such a cultural phenomenon, can you share a memory from filming that still makes you laugh or smile?

It’s hard to believe it’s been 21 years since it was released. I’ll never forget when we filmed Jingle Bell Rock for the first time. That was the moment I thought, “Wow, this is really a special movie.” And then there’s the party scene where Lindsay (Lohan) pukes on me. We had to use chicken soup to simulate the puke, but then they never ended up showing it in the final cut of the movie. I remember watching it back and laughing, saying we did all that fake puking, and it didn’t even make it in. But it’s really the friendships and memories between filming that really stand out for me like hanging out in Toronto at the Sutton Place Hotel with the cast, or making Thanksgiving dinner with Lacey (Chabert) and Amanda (Seyfried) at Lacey’s apartment. Not every actor gets to be in a movie that makes so many people happy, and I’m always so amazed every October 3rd (known as Mean Girls Day) and just all the love we still get to this day.



Lacey Chabert has been in many Hallmark movies as well, and I’m sure Mean Girls and Hallmark fans alike would love to see the two of you team up. Is that something we could ever expect?

Lacey and I have actually wanted to work together for a long time. We’re just trying to find the right project to make that happen.


Looking ahead in 2025, is there a career-specific or personal goal you’re aiming for? Any resolutions, perhaps?

In 2025 I want to direct a romantic Christmas comedy. So my next goal would be to direct a Christmas movie.

You can stream Finding Mr. Christmas, The Groomsmen, or Seasons’s Greetings From Cherry Lane on Hallmark+. For more, be sure to follow @jonathandbennett on social media!


This interview has been edited for brevity.

2025 SWAGGER MAGAZINE

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