Somewhere high in the Hollywood Hills, the wind blusters through the palm trees. There is a chair on a rug on an outdoor deck, and the backdrop is LA’s infinite sprawl spreading to the horizon in a soft focus haze. It is into this scene, this past September, that rapper Trippie Redd sauntered—wearing all black and neon and studded yellow sandals and socks—settling into the outdoor throne to deliver his Best Advice. Using his phone as a mirror, he pulled his dreads back from his face and flashed his bling-encrusted gold grill, he was ready to drop some knowledge.
The buzz on this Canton, Ohio native—who now resides in the City of Angels—began in his mid-teens, with his debut 2017 mixtape, A Love Letter to You, a clutch of melodic, slurry, hi-hat rattled raps that slid into the Billboard charts at number 64. Since then he’s collaborated with everyone from Young Thug, to Travis Scott, to the late rapper XXXTentacion, releasing three more high charting mixtapes and two major label full lengths, including his latest album, !, which charted at number three. While his lyrics pinball between topics such as mental health and heartbreak, to straight up flex and diss tracks, his influences are pure Gen Z: a melting pot of Nirvana, System of a Down, Kanye, Lil Wayne, and Drake.
At 20-years-old, Trippie Redd comes off remarkably self-assured. Ask him if he’s ever doubted himself and the answer is “Nah.” He says he listens intently to his mom’s advice, makes sure she knows she’s heard, but when it comes to applying those words of wisdom, Trippie goes his own way. Nevertheless there is one piece of advice that he adheres to, and it comes from the most unlikely of historical sources.
Watch this latest episode of Best Advice, above, and check out all our previous installments with Lizzo, Quincy Jones, Rick Ross, Karen O, and many more right here.