Hip-hop artists Sexyy Red, Ty Dolla $ign & Ski Mask The Slump God are set to join the cast of Rolling Loud, an R-rated hip-hop comedy inspired by the world’s largest hip-hop festival.

Also joining the cast is Henry Winkler (Happy Days, Barry). They will join Owen Wilson (Wedding Crashers) and Matt Rife (Trapped Inn). American High CEO Jeremy Garelick (The Wedding Ringer) will write, direct, and produce, while Live Nation Productions’ Ryan Kroft and Michael Rapino are on board as executive producers.

The story follows an overprotective father and cool dad wannabe (Wilson) who sneaks his 13-year-old son (Christian Convery) into a music festival. What starts as a simple bonding experience quickly turns into a chaotic adventure with his brash co-worker (Rife) and a quirky festival volunteer (Christine Ko). Along the way, they navigate through festival crowds, tight security, and unexpected family dynamics.

Back in December, Wilson joined Travis Scott for a surprise performance of “FE!N” at Rolling Loud Miami.

Sexy Red recently collaborated with Bruno Mars for “Fat, Juicy, and Wet.” Ski Mask the Slump God released his first studio album in five years with 11th Dimension, last year. Ty Dolla Sign worked with Ye (formerly Kanye West) for their supergroup ¥$ on Vultures 1 and Vultures 2.

Sexy Red and Ski Mask the Slump God are set to perform at Rolling Loud California on March 15 and 16 at Hollywood Park. which will be headlined by A$AP Rocky, Playboi Carti and Peso Pluma.

Last February, Rolling Loud graced Billboard Philippines’ first-ever POWER digital cover.

Ralph Regis

Ralph Regis

Lifestyle and Culture Writer

Ralph Regis is a Lifestyle and Culture Writer at Billboard Philippines, where he bridges the worlds of film, television, fashion, art, food, and cultural trends with both the local and international music scene.

He has written extensively about artist collaborations, brand partnerships, and pop culture moments that connect back to music. He also brings stories to life through in-depth interviews with musicians and personalities, drawing on their diverse perspectives, opinions, and reflections on the human condition.

In addition, Ralph also writes about music releases across a wide range of genres, including pop, hip-hop, P-pop, and rock, highlighting both rising and established artists. With a passion for storytelling that goes beyond trends, he explores how music is part of our daily lives in one form or another, connecting culture, experiences, and everything in between.

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