Jonathan Bennett Teases The Holiday Sitter, Taking “Comedy to the Next Level” at Hallmark

This Sunday, you can watch The Holiday Sitter, starring Jonathan Bennett and George Krissa, based on an original story by Bennett.

It’s a genuinely funny movie about Sam (Bennett), a confirmed bachelor with no interest in children, who winds up watching his niece and nephew over the Christmas holiday. Everything changes when he meets their neighbor, Jason (Krissa).

We jumped on the phone with Bennett to talk about it.

Hi, Jonathan. How are you?

I’m wonderful. How are you?

I’m good, thank you. You know, you’re somewhat of a legend at Hallmark.

Oh my God. Stop it. Tell me more.

Every time I ask somebody who they’d like to work with, you’re almost always at the top of their list.

You’re lying to me. Now you’re just flattering me. And let me tell you, flattery will get you everywhere with me, okay?

Yeah, people just really admire your work. I think that’s fantastic.

Oh, that’s very sweet. Thank you very much.

So, how would you describe your Hallmark journey so far?

Wow. My Hallmark journey has been such a rollercoaster because I think I’ve played so many different types of characters on the network, and I’ve been with the network for a long time.

And to watch the network completely just grow to the next level in so many ways has been such a fun ride to go on together.

And of course, now you’re a creator for the network, which opens up a lot of storytelling ideas for you, gives you a lot of freedom. What was the genesis of The Holiday Sitter?

Okay, so I grew up watching all the eighties comedies, and I loved movies like Uncle Buck, and I thought it was so funny that an uncle would come home and have to take care of his niece and nephew and not know anything about kids.

And as a gay man myself, I’m an uncle to so many of my friends’ kids in real life. So I thought, what a fun idea for a story.

So I said, what if the gay uncle comes home for the holidays and has to put on Christmas for his niece and nephew that he’s never really met?

And that’s where the idea was born, and I brought it up to the Hallmark Channel, and they were over the moon excited and supportive from the very get-go of creating this world for this character to play in.

So, that’s how The Holiday Sitter was born.

I really enjoyed the amount of comedy that you used. You had a really good mix of comedy, romance, and even some drama in there. How did you manage to get the whole gamut?

Well, I think what is important in storytelling is just to do what’s real. Because when you do what’s real, people identify with it, whether it’s emotional or funny.

And what we set out to do with The Holiday Sitter is just tell a real story of what a gay man in 2022, a member of the queer community goes through. And everything from dating to wondering if he can have a family of his own, to taking care of kids that he’s never been around.

So, I think when you just lean into the truth of every moment, that’s where you get the heart and the comedy.

And you have the honor of bringing a full story centered on same-sex romance to Hallmark. What does it feel like to plow that path and be the first one to do it, and I have to say, the first one to get it really right?

Wow, that means a lot. Thank you so much.

I’m just so proud to be part of the Hallmark Channel and telling this story because I know so many people are going to see it and feel represented, and so many people are going to see it and are going to be reminded that, hey, you have a place at the holiday table for Hallmark as well.

I think that’s so important. But on top of that, as a filmmaker feel, I just feel so blessed to have Hallmark Channel because what Hallmark Channel has done is they have given queer filmmakers a safe place to tell stories. And as an artist, there’s no better gift on earth.

That’s a wonderful way to put it.

They have been so supportive from day one of like, “We’re going to do this, and we’re going to do it right.”

I think it turned out great. I think it’s a really wonderful movie. And I have to tell you, there’s a scene where I laughed out loud, and it still makes me laugh just to think about it. [Scene talk edacted to save the fun for viewers]

It’s hilarious!

It really is. It really made me laugh out loud. And the way it was said and the look on your face, it was just perfect.

Thank you. I think the comedy really plays in this movie, and it’s pretty much… I don’t know. What do you think? It’s one of the more broad comedy movies you’ve seen at Hallmark?

Yeah, it really is.

I think The Holiday Sitter really takes comedy to the next level at the network. I think the way we were able to do that is by finding the perfect Jason because George is so good and so slow, and I’m such a crazy person on camera half the time.

So, it was a good mix to have someone like George Krissa playing Jason playing opposite all the wacky stuff I’m going to do.

And I think we found this great balance of when Jonathan’s doing something that’s absolutely insane, just do nothing, and we’ll be able to talk back to you doing nothing, and we’ll get a laugh.

Exactly. And it also works well from the romantic aspect too, because Sam is just floundering, and Jason has all these emotions, and it really plays well to lead into the end of the movie.

Oh, I know. What was so great is that we really told this story authentically because it was important for us to have a queer team leading this creatively.

So we had queer writers, directors, producers, and actors telling this story. So, we had all of these different personal stories to pull from, and that’s what Hallmark does such a great job of, making sure we told this story correctly. And we were able to do that cause of the creative team that was involved.

Well, you picked a great team.

Yeah, I’m so proud of it. There’s a little Mean Girls nod to it in the comedy, I think — a lot of the phone calls. Ali Liebert, our director, did a great job of having those phone calls that slide around and move in out of frame.

I think it was a little nod to the three way calling attacks in the movie Mean Girls, which we wanted to pay a little homage to. It’s got a new energy to it that is different from a lot of the other Hallmark movies.

I would agree. I think it turned out really well.

And the chemistry between me and George is probably the best chemistry I’ve ever had with someone on camera.

That says a lot.

Yeah, and especially because when we finally get to the end, that big moment at the end, I think the audience is waiting for it to happen, and it finally happens, and that was our goal.

Absolutely. How much of your real life do you draw on to play a character like this, which is really your first time of breaking out of the, what we’ll call traditional Hallmark roles that you’ve had? How freeing is it to be able to make this movie and play the role?

To get to set every day with a script that is perfectly written by Tracy and Greg, with a director that is top notch, and a producer that has your back, puts you as an actor in an incredibly safe space to try things and to be free.

And when you’re free and you have the freedom to just go for the joke every time, you’re able to test those golden nuggets because I can tell you, nine times out of ten, the jokes didn’t work. But you don’t feel stupid when it happens. You feel supported.

When you feel supported, you’re able to go for the jokes because nine times out of 10, are not going to work, and you have to be okay with them not working. But when you hit that tenth one, and it is a slam dunk, you get the gold, and that’s what makes it into the cut.

And how soon before we get another Jonathan Bennett original?

We’re in the middle of writing things right now, and I definitely want to continue to bring the Jonathan Bennett energy and the Jonathan Bennett life to camera in your movies. So, whether I play a straight character or a queer character, what’s not going to change is the Jonathan Bennett energy on the screen.

I’m glad you said that because I appreciate that you are willing to play both sides, straight characters and gay characters. Because that’s what an actor does.

Yeah. And I just, I do it all. I just like playing characters that I like, whether it’s straight or gay.

Absolutely.

If I like the character, and I think that the script is funny, I want to do it. Like, Wedding of a Lifetime, I played with Brooke D’Orsay, she and I had some of the other best chemistry I’ve ever had on camera with anyone. I don’t know if you saw it.

I did, yes.

Yeah, and there was a lot of comedy in that when I’m running around the streets and when we’re sneaking out of the hotel disguised. There’s a lot of comedy in that movie, and there are lot of funny moments.

And I think what matters at the end of the day is that you just play characters that you really feel good about, and that really ring true to you, and then all the comedy and all the chemistry comes.

Yeah, I would agree. And you mentioned Mean Girls, and Lindsay Lohan and Amanda Seyfried have been chatting about Mean Girls 2. Would you be up for that if it happened?

I feel like a Mean Girls sequel needs to happen, and I’m here for it every step of the way. I will do anything that Tina Fay and Lorne Michaels ask me to do because I owe my entire career to them, and there’s no better cast than the Mean Girls cast.

Good answer. That’s the answer we want to hear. And if you don’t mind my asking, how are you and Jaymes going to be spending your first married Christmas together?

Our first married Christmas, I’ll be in New York City spending Christmas at the Hotel Edison, my favorite hotel in New York, and we’ll be spending Christmas there because the day after Christmas, I start rehearsals to host the Time Square New Year’s Eve ball drop I do every year.

So we’ll have Christmas in New York.

Brilliant. What a wonderful place to spend Christmas.

Yep.

And my final question, watching Hallmark movies can become ritualistic, how would you suggest fans prepare to watch The Holiday Sitter?

Wow. Get cozy, get comfortable, and make sure you’re close to the bathroom because you’re going to laugh a lot.

The Holiday Sitter premieres on Hallmark Channel on Sunday, December 11 at 8/7c

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