How ‘Descendants 5’ Ventures Further Into the World of Wonderland and Introduces New Characters (Hello, Chessy the Cat!)

The battle between heroes and villains is back in a fifth installment of Disney‘s wildly successful Descendants franchise. 

Descendants: Wicked Wonderland, which premieres Thursday, revisits the world of Wonderland from Lewis Carroll’s classic books and sees the return of fan favorites from the fourth installment, including Red (Kylie Cantrall), daughter of the Queen of Hearts (Rita Ora), and Chloe (Malia Baker), daughter of Cinderella (Brandy). It also introduces several new characters, such as Pink (Liamani Segura), Red’s younger sister, and Chessy the Cat (voiced by Awkwafina), offspring of — you guessed it — the Cheshire Cat.

Greenlighting a fifth movie in the franchise was pretty much a no-brainer. Each of the first three films ranked as the most-watched cable movie of the year in which they debuted. Descendants: The Rise of Red, the fourth film, premiered on Disney+ as the most-watched original movie among kids and girls 6–11. Last year, the Descendants/Zombies Worlds Collide Tour played to sold-out crowds in more than 40 arenas across North America, and it’s hard to go out on Halloween without running into a child dressed as a character from one of the movies.

Charlie Andrews, executive vp live action, Disney Kids & Family, has some ideas about why the franchise continues to resonate with younger viewers more than a decade after it first premiered.

“The Descendants fandom is truly on another level, and I feel so lucky to be part of these movies,” he says. “The franchise connects with our audience in such a massive way because of the iconic characters, friendships, magic and — of course — the incredible music at the center of each film. Every time you watch a Descendants movie, you want to get up and dance and sing along to songs that have helped define generations. And beyond the fun and fantasy each film delivers, we explore identity in such a powerful way that resonates with any kid. Every viewer is on their own coming-of-age journey, finding the HK [Hero Kid] and VK [Villain Kid] within themselves, and they really see that reflected onscreen.”

In case you’re not familiar with the movies, Descendants blends characters from other Disney franchises, focusing on the offspring of iconic heroes and villains, often showing how they struggle with the labels placed on them and striving for acceptance from their parents as well as those who grew up on the other side of the story in the battle of good vs. evil. It kicked off in 2015 with Descendants, which starred Dove Cameron (as Mal, daughter of Maleficent), Sofia Carson (Evie, daughter of the Evil Queen), Booboo Stewart (Jay, son of Jafar) and the late Cameron Boyce (Carlos, son of Cruella de Vil). The first three movies followed that core group before the fourth installment pivoted to the world of Wonderland (though Alice isn’t part of this story). 

Descendants 5 picks up where the fourth movie left off, after Red and Chloe have traveled back in time to stop the prank that turned the Queen of Hearts evil: Now, she’s nice, Cinderella is safe, and things seem perfect for Red and Chloe. However, they soon learn that changing the past created a new villain: Maddox Hatter (Leonardo Nam), son of the Mad Hatter.

Kimmy Gatewood (Muppets Mayhem), who directed Wicked Wonderland, says she’s seen firsthand the impact of the movies on young viewers: Her 11-year-old daughter is a fan.

“It opened up her world to imagination and musical theater and singing and dancing,” Gatewood says of the first time her daughter watched Descendants. “This movie is obviously for her and all the children out there who are trying to figure out who they are and learning that they don’t have to be defined by their parents. We expanded the cast quite a bit, and I hope that all the kids out there can see a version of themselves or someone that they know in this film.”

For executive producer Suzanne Todd, Wonderland was familiar territory: In addition to exec producing Rise of Red, Todd was a producer on the Disney feature films Alice in Wonderland (2010) and Alice Through the Looking Glass (2016).

“Coming in [for Rise of Red], the assignment was, could we relaunch Descendants with some new characters?” she recalls. “I had already made two other Wonderland movies for Disney, and it’s a space that I’m really, really happy working in.”

Todd notes the long-lasting appeal of Carroll’s stories in pop culture, from fashion to music videos and more.

“Even though I had already done two movies in the space, there was still so much [to explore],” she says, noting how the fourth and fifth films combined tell a bigger story. “I love that there’s a throughline; you see the consequences of the actions in the previous movie. It’s not a whole new story; it’s like, OK, that happened and now this is what happened as a result of that.”

Indeed, the movies reveal valuable lessons to young viewers about taking responsibility for your actions, breaking out of societal expectations and learning to accept others. Wicked in Wonderland also focuses on friendships and emphasizes that “friendships are worth fighting for,” Gatewood says. “It also shows that you can be the hero of your own story.”

Todd says that the characters’ struggles with moral questions about who they are and whether their parents’ actions define them was part of the appeal of Descendants before coming on board as an exec producer (Gary Marsh, former president and chief creative officer of Disney Branded Television, also served as exec producer on the movie).

“What was probably most interesting to me about taking on Descendants is this idea of identity: Am I good? Am I bad? If my dad is bad, am I bad forever? If my mom is good, but I did something wrong, am I forgivable? I think it’s something that everybody struggles with at some point in their life.”

Gatewood agrees with that sentiment, noting that the characters struggle not just with the impact of their parents’ actions and behavior but also with the normal things that regular kids worry about. For example, “Luis Madrigal says in the movie, ‘I’m doing what people want me to be, I’m acting how people want me to act,'” Gatewood notes. “That’s something a lot of kids feel, like ‘I have to be the smart one, I have to be the strong one, I have to be this, that and the other, but it’s a lot more difficult to live up to these impossible standards. The fact that these characters all show their vulnerabilities is one of the reasons that kids keep watching the movies.”

Gatewood and Todd have high praise for their two young stars — Cantrall and Baker — who helped guide the greener actors, some of whom had never been on a set prior to Wicked Wonderland.

“Some of them were asking about, literally, how you find your mark when you’re coming into a scene,” Todd says. “They were very, very newcomers who were able to watch Kylie and Malia really step up in that way to be responsible. Not in a way that was like, ‘I know something that you don’t,’ it was, ‘I’m going to share what I’ve learned.'”

As for Brandy and Ora, Todd likens their friendship to that of Laverne and Shirley while they were on the set. The duo spent a lot more time together on Wicked Wonderland than they did in Rise of Red, as the plot finds them confined in very close quarters at one point. “They were like best friends, just hysterical, cracking each other up, cracking everybody else up,” Todd says. “I don’t know if you’ve ever been locked in a closet with your best friend for days on end, but I think they had a lot of fun. I’m happy to say we didn’t have to drag them to come back. They were happy to come back.”

In addition to the returning characters, Wicked Wonderland introduces several others. Along with Pink and Chessy, viewers will meet Luis (Alexandro Byrd), son of Luisa Madrigal from Encanto; Hazel (Kiara Romero), daughter of Captain Hook; and Maddox’s son Max (Brendon Tremblay). With so many heroes and villains in its library, Disney obviously has a wealth of characters to mine from, but the aim is to be more strategic about which ones make the cut for Descendants.

“The question is always: What does this character unlock thematically?” Andrews shares. “Luis, as Luisa Madrigal’s son, lets us explore a legacy-of-strength theme from a completely different angle than anything in the Descendants world so far — he’s not wrestling with villainy, he’s wrestling with living up to family expectations in a different way. Chessy gave us a built-in tone: mischievous, riddling, untrustworthy-but-charming, which is perfect for Wonderland’s logic. We’re very selective about which new characters we lean into to make sure they carry real narrative weight.”