He was the kid with the schemes. The little brother who always had a dollar sign in his eyes and a sarcastic comeback ready for his psychic sister. If you grew up in the mid-2000s, Kyle Massey was everywhere. As Cory Baxter, he wasn't just a sidekick; he was a comedic powerhouse who eventually landed Disney Channel's very first spin-off, Cory in the House. But then, things got quiet. You might find yourself wondering about Cory from That’s So Raven now because the transition from child stardom to adult life wasn't exactly a straight line for Massey.
It's weird how we freeze people in time. To a whole generation, he’s still that twelve-year-old in baggy hoodies trying to sell Raven’s secrets for lunch money. In reality, Kyle Massey is well into his thirties. His journey since leaving the White House—the fictional one, anyway—has been a mix of reality TV highs, music ventures, and some pretty serious legal hurdles that changed the trajectory of his career.
From the White House to the Ballroom
When Cory in the House ended in 2008, Massey didn't just disappear. He actually made a massive splash on Dancing with the Stars in 2010. He was the runner-up. People loved him. He had this infectious energy that proved he could perform outside the sitcom format. It felt like he was about to have a major second act. He was pairing up with Bristol Palin for a reality show and even lending his voice to Milo in the Disney animated series Fish Hooks.
He stayed busy.
For a few years, it seemed like he was successfully navigating the "former child star" minefield. He was doing voice work, appearing on game shows, and leaning into the nostalgia circuit. He and his brother, Christopher Massey (who played Michael on Zoey 101), were a staple duo in the Hollywood social scene. They were the Massey brothers. A package deal.
The Legal Clouds and Career Shifts
Honestly, the conversation around Kyle Massey shifted significantly around 2021. This is where the story gets heavy. He faced serious legal allegations involving a minor, which led to a lengthy court process. When looking for Cory from That’s So Raven now, it is impossible to ignore how these headlines impacted his public image and professional opportunities.
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The case moved through the Washington state court system for years. In 2023, the felony charge of communicating with a minor for immoral purposes was eventually dismissed. His legal team consistently maintained his innocence, citing a lack of evidence. While the dismissal was a legal victory for Massey, the "court of public opinion" is a different beast entirely. Careers in the entertainment industry are fragile. Even with charges dropped, the momentum he had during his Dancing with the Stars era had cooled significantly.
He stayed mostly out of the spotlight during the height of the legal battle. No big Disney reunions. No cameos in the Raven's Home spin-off during those years. It was a stark contrast to the boisterous, public-facing persona he had maintained for decades.
Why Wasn't Cory in Raven's Home?
This is the question every fan asks. Raven’s Home premiered in 2017. Most of the original cast popped up eventually. Anneliese van der Pol (Chelsea) was a lead. Even Adrienne Bailon came back as Alana. But Cory was missing.
The show explained it away simply: Cory was still in D.C. Or he was busy. The writers kept the door open, but the real-world timing never lined up. Between Massey’s personal life and the specific direction of the new show—which focused on Raven and Chelsea as divorced moms—there just wasn't a natural slot for the "President of the United States' former chef's son" to slide back in.
Recently, there has been more movement. Massey has expressed a desire to return to the character. He knows the fans want it. There’s a certain power in nostalgia that few things can beat. Whether or not Disney will pull that lever again depends on a lot of corporate factors we aren't privy to, but the demand is definitely there on social media.
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The Music and the "Brother" Brand
Kyle and Chris Massey have spent a lot of time working on music together. They aren't just actors. They've dropped tracks and performed at various events over the years. It’s a different vibe than the Disney pop era. It’s more independent, more experimental.
They also lean heavily into their status as 2000s icons. You'll see them at fan conventions or doing "90s vs 00s" themed nights. It's a living. And honestly? It’s a smart one. People who grew up watching That’s So Raven are now the ones with the disposable income to buy tickets to these events.
What is he doing right this second?
- Digital Content: He stays active on platforms like Instagram and TikTok, often posting throwbacks or glimpses into his daily life.
- Independent Projects: He’s been involved in smaller film projects and voice-over work that doesn't always hit the mainstream radar.
- Family Business: The Massey family is tight-knit. He’s often seen supporting his brother’s ventures and vice versa.
Acknowledging the Complexity of Child Stardom
Being Cory from That’s So Raven now means carrying the weight of a legacy that you didn't necessarily choose as an adult. We often demand that child actors stay "wholesome" forever. When they hit bumps in the road—whether those are legal issues, career lulls, or just the natural process of growing up—the public can be harsh.
Massey’s story isn't a simple "where are they now" listicle entry. It’s a nuanced look at a man who reached the literal peak of kid-fame and then had to figure out what happens when the cameras stop rolling on the laugh track. He’s survived scandals that would have buried other people. He’s still here.
How to Follow the Journey
If you want to keep tabs on what Kyle Massey is doing without relying on old reruns, here is how to navigate his current presence.
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Check his verified social media.
Don't rely on "nostalgia" accounts that post 20-year-old photos. His current Instagram is where he announces new music or public appearances. It’s the most direct way to see his current "vibe."
Support his voice work.
Many fans don't realize how much he’s done in animation. If you liked his comedic timing in That's So Raven, check out his work in Fish Hooks. It shows his range beyond just physical comedy.
Separate the character from the person.
When rewatching the old show on Disney+, enjoy the performance. Cory Baxter is a legendary TV character. Kyle Massey is a person who has lived a lot of life since that show ended. Understanding that distinction makes it easier to appreciate the art while acknowledging the reality of the artist's journey.
The most practical thing for any fan is to keep an eye on the trades regarding Raven's Home or future Disney+ specials. With the way reboots are currently trending, a "Cory" appearance is never truly off the table, provided the timing and the public climate are right.