Entertainment

Inside Kyle Massey’s Hollywood Comeback

Published

1 hour ago

25 August 2026

NewsAdmin

“That’s So Raven” and “Cory in The House” star Kyle Massey is stepping back into the spotlight, gearing up to headline his second comedy show at the famed Laugh Factory Hollywood. On August 26, the Disney Channel favorite will host a Birthday Comedy Jam, featuring sets from Massey, Tiffany Haddish, his brother Chris Massey, and a lineup of other celebrity guests. During an exclusive interview with The Blast, Kyle spoke with us about his major return to the Hollywood scene and detailed why now was the perfect time.

Fans are eager to see Kyle back in action after his first Laugh Factory show packed the venue, with an overflow crowd waiting outside to get in.

The response was so strong that Laugh Factory Hollywood invited the fan-favorite back for another round, this time alongside his brother, Chris.

“The audience certainly loves Kyle and Chris!! What a reaction. It was like having the Beatles in the house,” said David Fuhrer, President of Laugh Factory.

And Kyle’s return promises plenty of laughs, with the new show featuring celebrity guests and a deeper look at his personal story.

“The one thing about my comedy show is all of the stories that I tell are real, true stories,” Kyle told The Blast. “They’re hilarious, and it’s the uncut perspective of a child star growing up in Hollywood that a lot of these people don’t really understand.”

What Inspired Kyle Massey To Tell His Story In A New Way?

Fans may know Kyle from beloved sitcoms and fan-favorite reality competition shows, but his stand-up act is giving them a chance to see a side of the star they’ve never seen before.

In his conversation with The Blast, Kyle credited his brother, known to fans from the Nickelodeon classic “Zoey 101,” with helping push him toward his next career move.

Watching Chris find success on the stand-up circuit, coupled with encouragement from comedy heavyweights like Chris Tucker, gave Kyle the confidence to bet on himself.

“They inspired me to just get up there and just do it,” he said.

Kyle Massey Is Ready To Give Fans The ‘Real, Raw’ Story Of His Life

Elsewhere in our conversation, the “Being Mary Jane” actor opened up about making the leap into comedy, a space where he can ditch the script and give audiences an unfiltered look at who he really is.

“Growing up with so many funny people and in my family and around me has just kind of made it easier to transition to this, to this free [style] of comedy,” he said. “It’s because this is my story. This is, you know, there’s no one telling me [what to say].”

He continued, “This is me. This is me—raw, and, you know, some people aren’t going to believe half of the things that I say, but this is my perspective coming out as a child star.”

Kyle Is Staying On His Comedy, Focusing On New Show In San Diego In September

Kyle’s return to Hollywood has exceeded his expectations, and he’s already looking forward to what’s ahead. After his upcoming Birthday Comedy Jam, Kyle will hit the stage again on September 7 at Laugh Factory San Diego for an all-new show.

“You know, the focus is on the comedy right now. The comedy shows are going very well. I’ve been booked left and right,” he shared. In addition to his California stops, Kyle will also visit Detroit, Michigan and Orlando, Florida.