If you spent any part of the last decade watching Disney Channel, you know Bertram Winkle. He was the sarcastic, lazy, and surprisingly lovable butler to the Ross family. He hated his job, loved his "cheese of the week," and basically lived for his naps. But honestly, most fans have no idea that the man behind the apron is actually one of the most decorated stage actors of his generation.
Who plays Bertram on Jessie?
The actor who played Bertram Winkle is Kevin Chamberlin.
Born in Baltimore and raised in New Jersey, Kevin isn't just a guy who landed a sitcom gig. He is a powerhouse. You’ve probably seen his face in a dozen different movies and shows without even connecting the dots. He’s one of those "character actors" who completely disappears into a role.
In Jessie, which ran from 2011 to 2015, Kevin brought a level of comedic timing that made a cranky butler the heart of the show. It wasn't just about him being grumpy. It was the way he’d sigh or roll his eyes at the Ross kids—Zuri, Luke, Ravi, and Emma—that made the character feel real.
But here is the thing: while he was vacuuming the Ross's penthouse on TV, he was already a massive deal on Broadway.
More than just a butler: Kevin Chamberlin's massive career
Most people think of him as the guy who says "I'm not doing it" on Disney Channel. In reality, Kevin Chamberlin is a three-time Tony Award nominee. That’s a huge deal in the theater world.
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He didn't just get lucky. He’s been nominated for playing some of the most iconic roles in modern musical history:
- Horton the Elephant in Seussical (where he basically defined the character).
- Uncle Fester in the original Broadway cast of The Addams Family.
- Charlie in Dirty Blonde.
If you look at his filmography, it’s wild. He made his film debut in Die Hard with a Vengeance back in 1995. He played a bomb squad expert named Charles Weiss. Seeing "Bertram" in an action movie with Bruce Willis is a bit of a trip, but it shows how versatile the guy really is. He’s also been in Road to Perdition, Taking Woodstock, and even played the Wizard in Wicked on Broadway for a year.
Why he was the perfect Bertram
The writers of Jessie knew exactly what they were doing when they cast Kevin. Sitcoms often rely on tropes, and "the lazy butler" is a classic one. But Kevin didn't play him as a one-note joke.
He gave Bertram a soul.
Throughout the series, we saw glimpses of Bertram's personal life—his obsession with opera, his secret hobby of collecting things, and his genuine, though well-hidden, love for the kids. Kevin actually directed four episodes of Jessie himself. He wasn't just there to collect a paycheck; he was an integral part of the creative team that made the show a staple for a whole generation of Disney fans.
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Where is Kevin Chamberlin now in 2026?
You might think that after a long run on a Disney show, an actor might slow down. Not Kevin. Honestly, he’s busier than ever.
As of early 2026, Kevin is still deeply involved in the New York theater scene. Just this month, in January 2026, he’s been linked to the world premiere of a new production called When Playwrights Kill in Boston. He’s also recently performed his solo show, Finding the Joy, which has been a hit with fans who want to see the man behind the characters.
He also became a bit of a viral sensation on TikTok. During the pandemic, he helped spark the Ratatouille musical trend, showing off his singing voice to millions of Gen Z fans who only knew him as the butler. It’s kinda cool to see a veteran actor embrace new tech like that.
Surprising facts about the man behind Bertram
A lot of fans are surprised to learn about Kevin’s personal life because he’s always been pretty low-key. He’s been married to TV writer and producer Michael Gans since 2008. They’ve actually been together since the early 90s, which is like a century in Hollywood years.
Also, despite what you might see on those weird celebrity-relative websites, Kevin Chamberlin is NOT related to Emma Chamberlain. It’s a common question because the names are so close, but they are just two famous people who happen to share a (slightly differently spelled) last name.
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What to do if you're a fan
If you want to see more of Kevin’s work beyond the Ross penthouse, there are a few places to start:
- Listen to the Seussical Cast Recording: You’ll hear his incredible voice as Horton. It’s a far cry from Bertram’s grumbling.
- Watch "The Prom" on Netflix: He has a great role in this film adaptation, alongside stars like Meryl Streep.
- Check out his TikTok: Seriously, he’s @chamberlin.kevin. It’s wholesome, funny, and shows off his real personality.
- Look for his guest spots: He’s popped up in everything from Modern Family to A Series of Unfortunate Events.
The next time you’re re-watching Jessie and Bertram refuses to get off the couch to help Jessie with a mess, remember you’re watching a literal Broadway legend at work. He might be playing a guy who hates effort, but Kevin Chamberlin’s real-life career is the exact opposite. He’s a guy who has spent decades perfecting his craft, and it shows in every "ugh" and "hmpf" Bertram ever uttered.
To really appreciate his range, try tracking down a clip of him singing "Alone in the Universe" from Seussical right after watching a Bertram-centric episode like "The Butler Did It." The contrast is basically a masterclass in acting.
Keep an eye on Broadway listings for 2026. If Kevin Chamberlin is on the marquee, it’s a safe bet the show is going to be something special.