Our 6 Favorite Jonathan Bennett Hallmark Movies, Ranked| Woman's World

There’s a good chance you know him as heartthrob Aaron Samuels from the 2004 blockbuster comedy Mean Girls, but Jonathan Bennett has continued to have a wildly successful career in television and movies since those early days of Lindsay Lohan asking him what day it was in class.

Today, you can catch him acting across a wide array of films, and on January 23, he’s even set to make his on-stage debut in Spamalot on Broadway. However, the place we love to watch him most is from our cozy spot on the couch while he brings some of our favorite stories to life on the Hallmark Channel.

Here, read about his early career and our favorite Jonathan Bennett Hallmark movies!

Jonathan Bennett’s early career

Some of Bennett’s first credits were in shows like Dad, The Bill, All My Children and Law & Order: Special Victims Unit. However, it wasn’t until 2004 that his role in Mean Girls put him in the spotlight as a heartthrob, cast opposite Lindsay Lohan in the hit film.

Jonathan Bennett and Lindsay Lohan, 2004Kevin Winter/Getty Images

“It’s not a regular movie. It’s part of people’s lives,” he told Salon of his pivotal role in the cult classic comedy. “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.”

The hit film has transcended time in numerous forms across various generations. In 2018, the Mean Girls musical debuted on Broadway. Now, fans of the original film and Broadway show are anxiously anticipating the January 12 release of the newest film/musical adaptation of Mean Girls, starring Renée Rapp and Angourie Rice, with Christopher Briney reviving Bennett’s original role of Aaron Samuels.

In a 2023 interview with PEOPLE, Bennett said, “I’m super excited for the movie musical. I love that this movie has transcended multiple generations because of the writing of Tina Fey.” He continued, “I think the new musical movie is gonna be fantastic, and I hope that the new Aaron makes the character his own because it’s his time to interpret the character.”

After Jonathan Bennett’s Mean Girls role, you could find him in series and films such as Smallville, Veronica Mars, Cheaper by the Dozen 2 (2005), The Dukes of Hazzard: The Beginning (2007), Van Wilder: Freshman Year (2009) and more. His Hallmark debut came in the 2014 film Elevator Girl, but it wasn’t until 2015 that he earned his first starring role on the network in Romantically Speaking.

Jonathan Bennett Hallmark movies, ranked

Here, take a look at our ranking of some of our favorite Jonathan Bennett Hallmark movies he’s starred in over the years.

6. Christmas Made to Order (2018)

Gretchen (Alexa PenaVega) is passionate about her side hustle, Christmas Made to Order, a holiday decorating business. When she has a run-in with Steven (Jonathan Bennett), an architect, he decides to hire Gretchen to decorate for his family’s Christmas party.

As Steven and his family spend more time with Gretchen, they begin to love her. To show Gretchen he truly supports her passions, he convinces his firm to hire her, and when she declines, he offers her double. When this offer makes Gretchen feel as though she’s nothing but an employee to Steven, he must do what he can to prove otherwise.

5. Wedding of a Lifetime (2022)

Darby (Brooke D’Orsay) and Jake (Jonathan Bennett) have been together since high school and after a rut in their relationship, decide it’s best to go their separate ways and call off their engagement. When they find themselves entered in a “romantic relationship competition” after their town nominates them, they continue their charade of being a happy couple so as not to disappoint their friends and family. After the contest ends, will they call it quits or could this opportunity reconnect them once again?

4. The Christmas House (2020)

Summoned home by their parents, Mike (Robert Buckley) and Brandon (Jonathan Bennett) hope that in the wake of some difficult decisions their parents have had to make, the two brothers can recreate their Christmas house. Meanwhile, Brandon and his husband (Brad Harder) anxiously anticipate a call regarding the adoption of their first child.

3. The Christmas House 2: Deck Those Halls (2021)

In the follow-up to The Christmas House, Mike, Brandon and their parents have all enjoyed what life has thrown their way — from retirement to parenthood. When Mike gets the opportunity to participate in a celebrity home decorating reality TV show, what he doesn’t expect is that his opponent will drop out of the competition and his brother takes the opposing spot!

2. Christmas on Cherry Lane (2023)

Christmas on Cherry Lane follows the story of three separate couples going through various changes and major life events during the holiday season — one of these couples being played by Jonathan Bennett and Vincent Rodriguez III, who are in the midst of a major kitchen remodel who find out they’re going to be expanding their family in the midst of all their Christmas chaos.

“It is so fun bringing these stories to life on this network, we are just having so much fun creating these characters and creating these stories that include everyone,” Bennett told GLAAD.

1. The Holiday Sitter (2022)

In the first Hallmark film to put an LGBTQ+ couple front and center, Sam (Bennett) is a workaholic bachelor who gets recruited by his sister to babysit his niece and nephew when they learn that the baby they are adopting is being born earlier than they anticipated. Realizing he isn’t cut out for the job and is in need of backup, he enlists the help of Jason (George Krissa), their next-door neighbor and contractor working on the finishing touches of the baby’s nursery. When the baby’s arrival isn’t as speedy as anticipated and Sam must spend more time in his babysitter role, he starts to rethink the bachelor life he’s created for himself.

“It’s a classic fish out of water story that leaves so much room for laughs,” Jonathan Bennett told Slice. “And what’s so fun is that he falls in love with the hot, hunky neighbour next door who happens to be the carpenter building the addition onto the house. So you have two things that Sam’s never experienced: building and children, and you throw them into this world that is completely not his and hilarity ensues.”