Owen Wilson, Henry Winkler & Sexyy Red Star in ‘Rolling Loud’ Comedy

One of the world’s biggest hip-hop festivals is now inspiring a wild new comedy. Rolling Loud, an R-rated film starring Owen Wilson and Matt Rife, is bringing festival chaos to the big screen. The cast just got even bigger, with Henry Winkler, Sexyy Red, Ty Dolla $ign, and Ski Mask the Slump God joining the project, according to multiple reports.

First reported by Deadline last year, the project named after the iconic music festival, Rolling Loud is based on a true story. The film follows an overprotective father (Wilson) who, in an effort to be seen as the “cool dad,” sneaks his 13-year-old son (Convery) into the festival. Things quickly spiral out of control as they navigate wild crowds, security, and unexpected challenges alongside Wilson’s reckless co-worker (Rife) and a quirky festival volunteer (Christine Ko).

Production is currently underway in Atlanta, with Rolling Loud set for release in 2026. The film is written, directed, and produced by Jeremy Garelick, the CEO of American High, known for his work on Adam Sandler’s Murder Mystery 2. UTA Independent Film Group is handling worldwide rights.

Joining Wilson and Rife are some big names from Hollywood and the music industry. Three-time Emmy winner Henry Winkler (Happy Days, Barry) is stepping into the festival madness, while hip-hop stars Sexyy Red, Ty Dolla $ign, and Ski Mask the Slump God add to the energy. Interestingly, a bio for Winkler humorously claims he’s “working on a rap album that is expected to drop in 2029,” though only time will tell if that’s real.

The film’s executive producers include Ryan Kroft and Michael Rapino for Live Nation Productions, Pasquale Rotella of Insomniac, and Matt Zingler and Tariq Cherif of Rolling Loud. Garelick and Will Phelps produce for American High, alongside Stella Bulochnikov for Pat Solitano Productions. Rife and Christina Shams also serve as executive producers. Casting is being handled by Mary Vernieu and Findley Davidson for Betty Mae, Inc.

While Sexyy Red and Ski Mask the Slump God are making their way to the big screen, they’re also set to take the stage at Rolling Loud California, happening March 15-16 at Hollywood Park. The event will feature headliners like A$AP Rocky, Playboi Carti, and Peso Pluma.

Wilson didn’t just sign on for a movie about Rolling Loud—he also made a surprise real-life appearance at the festival. On Dec. 15, the actor shocked fans by stepping onstage during Travis Scott’s set at Rolling Loud Miami.

Fan-captured videos show Wilson joining the SICKO MODE rapper to perform “FE!N” from Scott’s 2023 album Utopia. After embracing Scott, Wilson hyped up the crowd, saying, “I’m feigning for more.”

Scott later posted a clip of Wilson’s appearance to his Instagram Story with the caption: “Made mi day.”

With production underway and a high-energy cast locked in, Rolling Loud is shaping up to be a festival adventure like no other. The film is expected to hit theaters in 2026, bringing hip-hop and comedy together in an unforgettable way. Stay tuned for more updates as the chaos unfolds!