It’s been over a decade since a bright-eyed nanny from Texas stepped into that swanky Upper West Side penthouse. Honestly, the Disney Channel era defined by the cast of Jessie feels like a fever dream now, but for a generation of fans, those four seasons were everything. You’ve probably caught yourself wondering while scrolling through TikTok if the Ross kids are still close, or if the "butler" is actually doing anything other than avoiding chores in real life.
By 2026, the landscape has shifted massively. Some of the cast members are dominating Broadway, others are leading gritty tech thrillers, and one is still very much the internet's favorite "cool aunt" figure. But it hasn't all been red carpets and sitcom laughs.
The Evolution of the Ross Siblings
When Jessie wrapped in 2015, the "Disney curse" was the big worry. Most of the kids defied it.
Peyton List is arguably the biggest breakout in terms of pure consistency. Most people know her as Tory Nichols from Cobra Kai, but as of January 2026, she’s pivoted hard toward the stage. She just officially stepped into the role of Heather Chandler in the Off-Broadway revival of Heathers The Musical at New World Stages. It’s a "bad girl" era that feels miles away from the fashion-obsessed Emma Ross, yet totally fits her trajectory as an executive producer on her other hit, School Spirits.
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Then there’s Karan Brar. If you still think of him as the kid with the giant lizard, you’re about ten years behind. In early 2026, Karan is starring in a tech thriller called Data at the Lucille Lortel Theatre. He plays Maneesh, a programmer caught in a Silicon Valley ethics crisis. It’s intense. He’s on stage for nearly the entire 90-minute show, sprinting through scenes with zero breaks. It’s a masterclass in how to transition from child star to serious dramatic actor without losing the audience's respect.
Skai Jackson’s Social Footprint
Skai Jackson (Zuri Ross) has taken a slightly different path. She’s become a powerhouse in the social media and voice acting space. While she’s done her fair share of reality TV—hitting the semi-finals on Dancing with the Stars a few years back—her 2026 vibe is very much "fashion icon and activist." She’s frequently seen at major industry events like the BAFTA Tea Party and the Golden Globes, maintaining a massive influence on Gen Z style.
The Unforgettable Cameron Boyce
You can’t talk about the cast of Jessie without a heavy heart for Cameron Boyce. His passing in 2019 from SUDEP (Sudden Unexpected Death in Epilepsy) was a gut-punch to the cast and the fans.
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Luke Ross was the heartbeat of that penthouse. He brought a kinetic energy that nobody else could replicate. Today, the cast still keeps his memory alive through the Cameron Boyce Foundation, which funds epilepsy research and works to reduce gun violence. Debby Ryan has often spoken about how Cameron was the person who would just sense when she was having a bad day and offer a hug without saying a word. His legacy is less about the episodes and more about the real-world impact his family continues to make.
Where Is Jessie Prescott Now?
Debby Ryan was the glue. She was actually the youngest female director in Disney Channel history at the time, which tells you everything you need to know about her ambition.
Post-Disney, she went through a "blonde phase" to distance herself from the red hair, starred in the controversial but cult-favorite Insatiable on Netflix, and eventually married Josh Dun from Twenty One Pilots. By 2026, she’s moved into more indie, character-driven roles. She’s expressed that Horse Girl (2020) was a massive turning point for her, and she’s continued to chase projects that are "weird" rather than "commercial."
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The Supportive Cast: Bertram and the Neighbors
Kevin Chamberlin, the iconic Bertram Winkle, is basically the internet’s uncle. Honestly, his TikTok game is better than most 20-year-olds. He’s a three-time Tony nominee, so the "lazy butler" persona was always just a brilliant act.
- Broadway Life: He recently starred in When Playwrights Kill in Boston.
- TikTok Fame: He went viral during the pandemic for his participation in the Ratatouille musical.
- The Memoir: He’s currently working on a memoir about his decades in show business, expected to drop in 2027.
And what about Mrs. Chesterfield? Carolyn Hennesy is still a legend in the soap opera world, continuing her long-running role as Diane Miller on General Hospital. She also voiced General Leia in Star Wars Resistance, which is a pretty cool pivot from being the lady who hated a lizard.
Surprise Careers
- Josie Totah (Stuart Wooten): She’s become a major voice in the industry, producing and starring in the Saved by the Bell revival and coming out as a transgender woman in 2018.
- Chris Galya (Tony the Doorman): He still pops up in indie projects like Dead Trigger and remains close with the cast.
Why It Still Matters
The cast of Jessie succeeded because they actually liked each other. In an industry where "set drama" is the norm, this group was a legitimate family. Skai Jackson mentioned in a 2024 interview that while they all live in different states now, they still "check up on each other."
If you’re looking to catch up with them today, your best bet isn’t the Disney Channel. Look toward the New York stage or the executive producer credits on your favorite streaming shows. They’ve outgrown the penthouse, but they’ve kept the work ethic.
Next Steps for Fans:
- Check out Karan Brar’s performance in Data if you’re in NYC before March 2026.
- Follow the Cameron Boyce Foundation to see how they are continuing Luke’s legacy through activism.
- Watch School Spirits on Paramount+ to see Peyton List’s transition into more mature, supernatural storytelling.