Descendants: Wicked Wonderland Expands the Magic With New Faces, Fresh Storylines, and Chessy the Cat

Disney's Descendants Franchise Returns With Its Fifth Installment

Disney's beloved Descendants franchise is back, and this time it's going deeper into the rabbit hole. Descendants: Wicked Wonderland, the fifth chapter in the long-running series, premieres this Thursday and promises to deliver everything fans have come to love — iconic characters, catchy music, heartfelt themes, and a whole lot of magic.

The new film continues the journey of Red (played by Kylie Cantrall), daughter of the Queen of Hearts (Rita Ora), and Chloe (Malia Baker), daughter of Cinderella (Brandy). Picking up directly from the events of the fourth film, Descendants: The Rise of Red, the story explores what happens when time travel fixes one problem but creates an entirely new one.

What Happens in Wicked Wonderland?

At the end of the fourth film, Red and Chloe traveled back in time to prevent the prank that originally turned the Queen of Hearts wicked. Their mission appeared to be a success — the Queen is now kind, Cinderella is safe, and life seems idyllic. But as any Descendants fan knows, things are rarely that simple.

Their interference with the past has given rise to a brand-new threat: Maddox Hatter (Leonardo Nam), the son of the Mad Hatter, who has emerged as the film's central villain. The story reinforces one of its core messages early on: actions have consequences, even when those actions come from a place of good intentions.

Exciting New Characters Join the Wonderland Universe

Chessy the Cat — Voiced by Awkwafina

Perhaps the most buzzworthy addition to the franchise is Chessy the Cat, voiced by comedian and actress Awkwafina. The offspring of the legendary Cheshire Cat, Chessy is described as a mischievous, riddle-loving, and delightfully unreliable character who serves as a guide through the film's new timeline — though viewers may want to take everything she says with a grain of salt.

"She's a mischief maker," says director Kimmy Gatewood. "Awkwafina is just a pro — so funny and sly. You never quite know whether to trust her, and that's exactly what makes her so compelling."

From a storytelling perspective, Chessy was a natural fit for the Wonderland setting. Her built-in personality traits — charm, unpredictability, and a knack for finding people's pressure points — make her a perfect addition to the Descendants universe.

Other New Faces

The film also introduces several other new characters who bring fresh thematic depth to the story:

• Pink (Liamani Segura) — Red's younger sister
• Luis (Alexandro Byrd) — son of Luisa Madrigal from Encanto
• Hazel (Kiara Romero) — daughter of Captain Hook
• Max (Brendon Tremblay) — son of Maddox Hatter

Each new character was chosen deliberately. "The question is always: What does this character unlock thematically?" explains Charlie Andrews, executive VP of live action at Disney Kids & Family. "Luis, as Luisa Madrigal's son, lets us explore a legacy-of-strength theme from a completely new angle. He's not battling villainy — he's struggling to live up to extraordinary family expectations. Every new character has to carry real narrative weight."

Why the Descendants Franchise Keeps Winning

The decision to greenlight a fifth film was easy. The first three Descendants movies each ranked as the most-watched cable movie of their respective release years. The fourth installment, The Rise of Red, debuted on Disney+ as the top-performing original film among kids and girls aged 6 to 11. On top of that, the Descendants/Zombies Worlds Collide Tour sold out over 40 arenas across North America last year alone.

Andrews attributes the franchise's enduring popularity to its powerful combination of iconic characters, genuine friendships, fantasy elements, and music that gets audiences on their feet.

"Every time you watch a Descendants movie, you want to get up and dance," he says. "Beyond the fun and fantasy, we explore identity in a way that resonates with any kid. Every viewer is on their own coming-of-age journey, finding the hero and villain within themselves — and they see that reflected onscreen."

Themes That Connect With Young Audiences

At the heart of every Descendants film is a question that resonates far beyond childhood: Am I defined by where I come from?

Executive producer Suzanne Todd — who also produced Disney's Alice in Wonderland (2010) and Alice Through the Looking Glass (2016) — says this theme was central to her interest in the franchise.

"If my dad is bad, am I bad forever? If my mom is good but I did something wrong, am I forgivable?" Todd reflects. "These are questions that everybody wrestles with at some point in their life."

Director Kimmy Gatewood echoes this sentiment, pointing out that the characters don't just grapple with the weight of their parents' legacies — they also face the very relatable pressures that everyday kids experience. One character in the film, Luis, openly admits to feeling trapped by others' expectations of him, a struggle many young viewers will instantly recognize.

"The fact that these characters show their vulnerabilities is one of the biggest reasons kids keep coming back," Gatewood says.

Behind the Scenes: Star Power and Strong Bonds

Gatewood and Todd both praised lead actresses Kylie Cantrall and Malia Baker for stepping up as mentors to newer cast members, many of whom had never set foot on a professional film set before Wicked Wonderland.

"Some of them were literally asking how to find their mark when entering a scene," Todd recalls. "But Kylie and Malia led by example — sharing what they knew in a generous, collaborative way."

On the other side of the generational divide, the chemistry between Brandy and Rita Ora was reportedly electric. The two spent significantly more screen time together in this installment than in the previous film, and Todd compares their off-screen dynamic to that of classic comedy duo Laverne and Shirley.

"They were cracking each other up constantly," Todd laughs. "I don't know if you've ever been locked in a closet with your best friend for days, but they made it look like a great time."

The Legacy of Wonderland — and the Descendants Universe

For Suzanne Todd, returning to Wonderland for the fifth Descendants film felt completely natural given her deep history with the source material. She notes that Lewis Carroll's world continues to inspire everything from high fashion to music videos, proving that its cultural appeal shows no signs of fading.

"Even after two prior Wonderland movies, there was still so much left to explore," she says. "I love that there's a throughline between the fourth and fifth films — the consequences of one story ripple directly into the next."

The Descendants franchise itself began back in 2015, starring Dove Cameron, Sofia Carson, Booboo Stewart, and the late Cameron Boyce. The first three films followed that original core group before the fourth installment pivoted toward Wonderland. With Wicked Wonderland, the series continues to evolve while staying true to the themes that made it a cultural phenomenon in the first place.

For young viewers searching for stories about identity, belonging, friendship, and the courage to write their own narrative, Descendants: Wicked Wonderland arrives right on time.