“You'd see Vic Mensa just walking down the street. “I remember the day 10 Day came out and Chance did his release party at Leaders,” he says, recalling the era that made him fall in love with Chicago rap. He brought his camera wherever he went and documented the scene, which included rising artists like Chance the Rapper, Vic Mensa, and Mick Jenkins. As soon as he got his driver’s license, Bennett got in a routine of making the hour-long trip to the city every weekend. Years before it became a full-time job, Bennett launched Lyrical Lemonade when he was a high school student in the small Illinois town of Plano, looking in from the outside on a vibrant Chicago hip-hop community. The growing list of artists who have been launched to mainstream success after landing videos on the Lyrical Lemonade channel includes Juice WRLD, Lil Xan, Blueface, and Lil Pump. Anchoring his work around playful animation and a run-and-gun production technique, Bennett has become the most in-demand director for an entire generation of rappers. His YouTube channel, full of music videos that he still edits himself, has gained a reputation in the industry as one of the most reliable places to discover the next big stars in rap, and it’s followed by over 10 million subscribers. He has built his Lyrical Lemonade company into an empire that now includes an events business, a media outlet, a production house, and a beverage distributor.

It’s uncommon for a music video director to get as much fan mail as Cole Bennett does, but the 23-year-old has already proven he’s anything but a traditional director. “They know I really like The Simpsons, so they just send me stuff,” he says with an appreciative grin. They were mailed to him from a fan-one of many packages he receives from young admirers around the world on a regular basis. As Bennett plays with a Homer Simpson figurine, he reveals that the toys weren’t a self-indulgent purchase.

The latest addition to the space, which he calls “the nostalgia room,” is a box of memorabilia from his favorite TV show, The Simpsons. Cole Bennett is crouched inside a tiny room of his Lyrical Lemonade office in Chicago, excitedly showing off a collection of vintage toys and old Nintendo 64 games.

Lyrical lemonade