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Taylor Bennett has been a fixture in Chicago’s Hip-Hop scene for years, but he knows success is rarely achieved alone.
During Day 1 of Lyrical Lemonade’s Summer Smash Festival, Bennett caught up with Hip-Hop Wired and reflected on the early days of his career alongside festival founder Cole Bennett. Looking back on how far both of them have come, the Chicago rapper recalled the first show they ever put together.
“I’ve known Cole [Bennet] since I was a kid, we put on our first show together in the Music Garage. In a room that held like 50 people, it was packed out, but this is f*cking crazy.”
The moment served as a full-circle reflection for Bennett, who has witnessed Lyrical Lemonade evolve from a grassroots platform into one of the most influential brands in Hip-Hop.
Taylor and his brother, Chance The Rapper, know a thing or two about longevity. Both artists have remained active and committed to their craft over the years. Chance returned with his latest solo album, STAR LINE, last year, marking a new chapter in his career following the mixed reviews to his 2019 project, The Big Day.
Meanwhile Taylor continues to build on his own momentum. The Chicago MC released his latest project, Time After Youth, last month, further showcasing his growth as an artist and storyteller.
Bennett also shared which Chicago artist have been in heavy rotation lately, naming Lil Mu, Adam Killa, himself, and, of course, his brother Chance The Rapper.
As Summer Smash continues to celebrate Chicago’s thriving music culture, Bennett’s story stands as a reminder of how far the city’s artists and the platforms supporting them have come.
Check out the full interview below.

