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Kimmy Gatewood Brings Descendants: Wicked Wonderland to Life

Disney/Alberto Rodriguez

When Kimmy Gatewood isn’t cracking jokes or landing body slams on Glow, she often finds herself in the director’s chair. She has credits from TV hits like Crazy Ex-Girlfriend, Girls5eva, and Muppet Mayhem. Throughout all these television series and in her own life, Gatewood has had a deep connection to music. You may recognize her from her musical comedy group, The Apple Sisters, or perhaps her star-making role as Snoopy in You’re a Good Man Charlie Brown at Briggs Chaney Middle School.

Now, Gatewood is in the director’s chair for the latest installment of the juggernaut Disney Original Movie franchise. Descendants: Wicked Wonderland is the fifth film in the Descendants series. It’s the most ambitious chapter in the story of these characters, and it’s Gatewood who was tasked with bringing this musical version of Wonderland to life.

Film Obsessive: What was the moment when you were a kid that you were like, man, I love this. I want to do this for the rest of my life.

Kimmy Gatewood: Where I lived in Maryland, it was very rural. Like horses in the backyard. I remember when the first McDonald’s came in. That was big-time.

I did watch a lot of Comedy Central when it came out. I would stay up late at night and watch Short Attention Span Theater and Mystery Science Theater at midnight. I was like, God, that looks really fun.

My grandparents took me to my very first show, which was Raggedy Ann and Andy at the Kennedy Center. Then they took me to Into the Woods, which was my second show. I saw the character of Little Red Riding Hood and, I was like, this is all I want to do. She was just so funny, sassy, powerful, silly, and a boss. I really identified with that character a lot. From there, I did the Maryland Renaissance Festival. I took improv through high school and did the plays in middle and high school.

Then, I was either going to go to the University of Maryland for biomedical research or Syracuse University for theater. I remember my college essay was called something like tap dancing biomedical researcher. Clearly, I was split in half. Ultimately, I said if I get into Syracuse for theater, I’m just going to do it because this will be the sign.

Kimmy Gatewood poses on the Descendants: Wicked Wonderland red carpet
Disney/Alberto Rodriguez

Do you still have an interest in biomedical research? Do you feel there’s an analytical part of your brain that directing scratches but acting doesn’t?

Definitely. Because half the job of directing is a weird math problem. The factors are always time, budget, story, and visuals. You’re balancing all those things and constantly trying to recalculate how I make this work and how to make this work.

Maybe because I didn’t go to film school or anything, perhaps it gives me this weird advantage of approaching things differently. You can make the impossible possible. Sometimes that’s just the job, you know?

If you think about science, you have this problem and you have a hypothesis of how you’re going to figure out how to solve the problem. You have to go about it a bunch of different ways, and I feel like the arts are very similar. Specifically with directing, when you’re like, we got the location, we got the actors, we got everything. Then you lose the location, you lose the actors, and you’re like, okay, let’s figure this out again.

With improv, you have to be free, you have to be open, you have to be in the moment. Whereas science, at least to me, is more structured. How do you balance these two aspects of your brain? When do you listen to the improv tendencies as opposed to the science ones?

This is making me sound so smart. Thank you so much. In prep, that’s when my science brain turns on. Those quiet moments when I’m doing a shot list, it’s like a formula. How can I do this and in what order? Then as soon as I get to set, I basically have to be prepared to throw it all away and be inspired by the moment because I’m trying to capture lightning in a bottle.

In science, you have to be open to discovery. It’s often just extreme problem solving. I think that’s why a lot of directors enjoy puzzles and game nights. It’s fun diving into the unknown. I like the concreteness of science and math, but there’s just something…I mean, you have to be a crazy person to be in the arts. It has to be all you think about, and it is all I think about.

You’ve directed some musical projects before coming on to Descendants. Is there something easier about doing musicals as opposed to the traditional drama, and vice versa?

Musicals are essentially an action movie because you have these massive sequences. Maybe they don’t have explosions, but they have intricate choreography that needs to be perfect, that needs to be rehearsed. You have to think about the costumes of the actors and you have to think about the ground they’re standing on. You have to think about so many different things and elements that it’s quite technical. I just turn on my James Cameron brain and think about what technology I need to invent to make this happen.

The most fun part about a musical number for me is that there’s so much prep that goes into it that the day of the shoot is utter joy. It’s really fun to do because everyone knows their steps, everyone knows the song and can sing. I really like it because it bonds people. I find that song and dance really frees people from being too self-conscious because they’re doing it together.

Red and Chloe walk toward the camera
Disney/David Astorga

I found the same thing when I was wrestling on Glow. We were all learning how to wrestle and it really bonded us as a cast. The crew was very protective of us. I find that same kind of spirit in all musicals that I direct. There’s a protective nature and there’s freedom.

The “Dancing with the Enemy” music video just came out and you can see these incredible chess-piece costumes. Think about the actors who had to dance in that, see where they were going, and coordinate all of that. Then you have all the kids. Some of them are being flung off the board, being attacked by giant flowers, and doing backflips.

Speaking of Descendants: Wicked Wonderland, what was it like to create your own version of Wonderland? What were you most excited to do?

I was really excited about the weird flora and fauna. I wanted every part of Wonderland to feel alive. It’s a little evil, a little good. I wanted the kids to feel like they couldn’t ever get comfortable. They’re dealing with this big bad guy too.

If I could have one dream out of this whole thing it’s that kids will build their own version of Wonderland in their house. Just goof around and make their own fun house. I hope it ignites this imagination.

Everyone who works in film wants to have a cool answer about the movies that got them interested in the industry, but I’ve long said that it’s the Disney Channel Original Movies that inspired me to do this. They were all so different. Having directed one, do you see these films having a role in not just igniting a lifelong love of film, but in opening young people’s eyes to different perspectives and different worlds?

The fun thing about jumping into this was asking myself, okay, what am I referencing here? Immediately, I was like, Honey, I Shrunk the Kids, Jurassic Park, Raiders of the Lost Ark, Goonies. All of these movies shaped me. The power that the Descendants franchise has in inspiring kids is unbelievable. I think kids feel seen in it on an emotional level. It’s hard growing up because you’re stuck between being a kid and an adult for a long time. People expect big things from you, but you’re still like, but I want to hug my mom.

The Smee twins sit in Wonderland
Disney/David Astorga

I hope we introduce all these new characters and each kid can find something within these characters. I identify with the Smee twins because they’re clowns and they’re the people who are slightly underestimated but always having fun.

You have Red and Chloe, who are obviously opposites. All these characters share an undercurrent of you don’t have to live up to the expectations of your parents. You can define your own path.

I think for the filmmaking side, this movie is probably the most ambitious one the Descendants franchise has ever been made, just because we were literally building a whole world. I hope that people seeing a mushroom get up and run away, a giant cookie in somebody’s hand, and these giant chess pieces on this giant board will make somebody go like, wait a minute, I could make something like that. I can dream that big too. It’s possible.

If you could turn any classic movie you grew up with into a musical to direct, which would you pick?

That’s a great question. Wouldn’t Jurassic Park the Musical be so funny? There’s a video of me making the cast sing the Jurassic Park theme as they enter Wonderland on set. I was like, picture this, a giant half-giraffe, half-zebra. Who doesn’t want singing dinosaurs, right?

The raptor sequence in that cafeteria would be so good.

It’s like a little West Side Story situation. Then the T-Rex is running. It becomes his ballad moment.

The T-Rex is actually the hero defending its land.

Oh my gosh, he’s just saying, please, I’m trying to reach out and connect with you, but they think he’s a monster. He’s Frankenstein’s monster in this story.

There we go. That’s it, that’s how you revitalize it!

Written by Tina Kakadelis

News Editor for Film Obsessive. Movie and pop culture writer. Seen a lot of movies, got a lot of opinions. Let's get Carey Mulligan her Oscar.

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