On Lindsay Lohan’s reaction to him in the audition room, his surprise kiss with Jamie Lee Curtis, and the real reason his hair was so long. Photo-Illustration: Vulture; Photo: Everette Collection

It’s totally easy to understand why an alt-rocking 15-year-old girl circa 2003 would crush hard on Chad Michael Murray’s Jake in Freaky Friday. No square-jawed jock, this guy worships the Hives and the Vines. He rides a Ducati and wears a leather jacket. His hair is manageably long. He’s too cool for high school, but not in an eye-roll-y way. So of course Anna Coleman (Lindsay Lohan) swoons after their first official conversation. Tons of potential!

But that was on a Thursday.

On its 20th anniversary, Freaky Friday remains a millennial classic for many reasons. Watching an ultragame Lohan and Jamie Lee Curtis — as her uptight, soon-to-be-wed therapist mom, Tess — wake up in each other’s bodies and try to adapt to the mystical swap without letting anyone in on the secret certainly ranks at the top. But let’s not sleep on Murray’s effortlessly appealing performance. His character didn’t exist in Mary Rogers’s original 1972 book, and there were no Jakes in the 1976 big-screen comedy (starring a young Jodie Foster) and the 1995 ABC TV movie. It was up to the actor to make Jake his own.

“He kind of had a swagger to him,” Murray says. “He was nonchalant about a lot of things except for his honest feelings about both girls in his life. He wasn’t full of anything other than ‘This is who I am, this is what you get.’ And that was it. I liked that.”

Jake never did learn that Anna and Tess unwillingly switched bodies overnight. That’s why he’s appalled at school when his peer begins acting like a holier-than-thou adult. And it’s why he finds himself suddenly enamored with her rules-breaking “mom”, joining her in an off-key rendition of “… Baby One More Time” while cozying up to each other at a coffee house. Even when Jake watches Tess as Anna vamp with her band on stage at the House of Blues and realizes she’s not as uptight as he thought, he has no clue that he’s really watching her mom, letting loose for the first time in years. (At least Anna is back to her regular self by the time they share a first kiss.)

Murray was perfectly cast as the object of affection. The de facto homecoming king of the WB in the early aughts, he landed the role after popular arcs on Gilmore Girls and Dawson’s Creek. Less than two months after Freaky Friday became a surprise box-office hit, he started his six-season run as heart-of-gold hero Lucas Scott on One Tree Hill. He currently co-stars in the Canadian series Sullivan’s Crossing, set to air on the CW in the fall.

And yet, he says, “To this day, no matter where I am — I can be at Disneyland traveling around the world or an airport, and always, someone will come up to me about Jake. Murray told us everything, from Lohan’s reaction to him in the audition room to his surprise kiss with Jamie Lee Curtis. (Note: This interview was conducted before the SAG-AFTRA strike.)

What do you remember about how this part came to be? 

I went through the typical casting process. I was reading with a bunch of guys. I know one of them was Jared Padalecki. We were buddies and goofed off before the audition. But I went through the process and had the opportunity to go to Disney and read with Lindsay in front of [director] Mark Waters. I believed in myself and had fun with it.

Did you consider it a “make or break”?   

As an actor, every single audition is a make or break. And I say that with all the hysterical comedy that comes with it. But I do remember being an overconfident 19-year-old. And I don’t know where that stemmed from. I think I had far more confidence than brains. So when I walked into the room, I knew I was in the right place at the right time.

Do you think that’s why you got cast? 

Oddly enough, I just worked with Mark in Thailand about a month ago [on the upcoming Netflix comedy Mother of the Bride]. Twenty years later, he told me, “It’s funny. I knew right away from the moment that you started acting in the scene with Lindsay. I could tell just from her reaction to you being in the room.” I don’t know how he meant it. I just know that he saw a reaction he was hoping to get, and the rest is history.

Annette Bening and Kelly Osbourne were originally tapped to star. Did you interact with them at all? 

I didn’t know that about Kelly Osbourne! When I signed on, it was Annette Bening and Lindsay Lohan. I think she was coming off an Oscar nomination? I found out a few weeks before shooting that Jamie was coming on. We were almost done with preproduction.
From that moment, I kept thinking how I’d get to go home and tell my dad that I kissed Jamie Lee Curtis! How cool is that?

Did you and Jake share any similarities at the time?

Some of the wardrobe. I had an OCD thing where I always had to wear a necklace. I believe I’m wearing a football necklace. It looks like a choker. It’s actually a football. And Mark dug it.

When Tess is in Anna’s body, she tells Jake, “I’m sure with the right haircut, you’d be quite presentable.” Seriously, what was going on with it? 

Mark said, “Keep it. I love it. Don’t touch it.” It was the first time in my life I had my hair long. I think I was in a place where I was just growing out my hair through the holidays and it must have been around February or March that I read for Mark, and it was still long. It’s long again right now.

Did you get to ride the Ducati? 

I wasn’t allowed because of the insurance policy. So I could only start it and stop it. When we’re driving down the street, and she’s snuggling up on the back of me? That’s the stuntman. I know.

What was Lindsay like back then?

Awesome. I mean, she was so young. We all were just a bunch of kids goofing around making a movie. She would talk and hang out, but she had so much work, right? I never really wanted to bother her. And when there was a big setup or downtime, she’d have to go to school. That’s one of the downsides when you’re a child actor.

May I ask if she was a good kisser? 

[Laughs] I don’t really recall. You’re so focused on the choreography and camera angles. But there is a funny story there. So Lindsay was really nervous, as anyone would be for a first onscreen kiss. And I guess Jamie, who’s a total pro and has been doing this forever, was trying to relax her. She’s like, “It’s going to be great! It’s going to be awesome!” Somehow it gets to the point where I hear a knock on my trailer door. It’s Jamie, and she goes, “Come, come, come.” Now I’m in her trailer and Lindsay is in there. And Jamie says, “We just want to talk to you about this onscreen kiss.” I’m like, “Okay, great, whatever makes you comfortable. We’re going to crush it.” And Jamie says, “See? Don’t even worry about it! You’re just doing the work.”

Then what happened?
Ultimately, long story short, Jamie goes, “Forget about it, come here.” And she kisses me and pulls away and goes, “See? It’s easy! It’s nothing! Right, Chad?” I’m like, “Oh, it’s great! Fantastic!” And from that moment, I kept thinking how I’d get to go home and tell my dad that I kissed Jamie Lee Curtis! How cool is that? We grew up watching True Lies, Trading Places. Halloween to this day is my favorite horror movie. What a trooper she is for just leading the way and breaking it down so simplistically for Lindsay and trying to make her feel comfortable.

Were you comfortable flirting with her in the coffee house? 
That was the first scene I shot. And of course I’m nervous, because it was one of those opportunities of just getting into the industry and you’re going up against someone who’s been around. It wasn’t uncomfortable flirting with Jamie; it was just nerve-racking to not screw it up. Like, am I flirting too much? Too little? [Whispers] Am I coming off creepy? You worry about all those things. But Jamie was the best and was right there supporting me.

What’s the story behind the use of the Britney song? 

Mark sent it to me the night before filming. It wasn’t originally in the script. He said, “I have this idea — do you remember the movie Say Anything? John Cusack is standing outside and holding the speakers in the air? I want to do that moment.” I told him I can’t sing, and he said, “Even better!” We shot it in a neighborhood where everyone was already asleep. I felt so bad for them. They were none too pleased with our lights and me terribly belting Britney Spears at all hours of the night.

There’s no way Jamie actually played that guitar in the wings while Lindsay was onstage at the House of Blues, right? 
So there were thousands and thousands of extras. It took forever to round them up. And it was so sweltering hot in there. But the girls crushed it! And Jamie learned that solo and she studied and studied her butt off. And then she studied Lindsay’s backing so she could flip it and play the whole thing. It was crazy.

Did you know right away that Freaky Friday was a hit? 

Can I say the truth? I didn’t know. Oblivious 19-year-old alert. I didn’t know until I read an article the following year and I saw that Disney had the top movie in the action genre with Pirates of the Caribbean and the top comedy with Freaky Friday and the top animated movie [Finding Nemo]. That’s when I realized it was successful. But I was just a kid running around, trying to make movies and live out a dream. Also, I was told to never read reviews. I still don’t.

But didn’t fans shriek when they saw you? 
I don’t remember! My memory is shot. I don’t know why. I’ve never touched a drug in my life, so it’s not that. My memory for some reason is very diluted.

Then, generally speaking, what’s your all-time freakiest Freaky Friday fan experience? 
I was in Thailand. We were at a grocery store in Phuket. The girl did not speak English very well but spoke it enough to have a small conversation. And she just went up to me and said, “Jake, Freaky Friday.” I smiled and was so awestruck. I take a 23-hour flight and she can identify me!

Have you been in touch with Jamie or Lindsay? 

I saw Jamie on the set of Scream Queens. Glen Powell and myself and Patrick Schwarzenegger played brothers. I gave her a hug. I also secretly saw her at Disneyland. We were on the same train, but I didn’t want to bring any attention to her because she was incognito. I gave her a wink and a nod. I haven’t seen Lindsay in about 15 years. But I’m a homebody and an introvert. I’m not great socially.

The sequel was announced a few months ago. Are you involved? 

They announced it, and then everyone went on strike. So I think the development is on hold for the moment. It would be awesome to come back and have Jake come in and reenter the world of mayhem. It would only be that much more interesting having Jamie potentially play a grandma or Lindsay playing a mother and Jake entering that world in some weird, bizarre way or still a part of it. It would be fantastic. I’d be all in.

Do you still have the football necklace? 

I do! I kept every necklace from every job. I have a box in the garage. Although it’s ripped. It was pleather, so it wore out.