Dylan Dilinjah was on top of the world after his appearance on Making The Band 2. His rap career was taking off, and he was set for stardom. That is until Dave Chappelle decided to poke fun at him in a skit on Chappelle’s Show.
Dylan appeared as a guest on the WeAreFlatbush Podcast detailing his early years of growing up in East Flatbush, Brooklyn & how he got his start in music and eventually becoming a rising star in the early 2000’s.
At first, Dylan tried to take the joke in stride. After all, being made fun of on a popular comedy show could have been seen as a badge of honor. But as time went on, the repercussions of the skit became too much to bear. Promoters didn’t want to book him, DJs didn’t want to play his music, and record labels wouldn’t even give him the time of day.
“It was like overnight, my whole career just went up in smoke,” Dylan lamented. “I had a newborn at home to take care of, and suddenly I couldn’t even afford to put food on the table. The joke had taken on a life of its own, and it was consuming me.”
Desperate to salvage his career, Dylan tried to pivot. He launched a craft beer and started a radio show, finding some success in those ventures. But deep down, he knew that his true passion was in music, and the skit had effectively ruined his chances of making it in the industry.
As the years went by, Dylan continued to struggle to shake off the stigma of the skit. People in the music industry still saw him as the guy that Dave Chappelle had made fun of, and he couldn’t break free from that image.
Now, years later, Dylan looks back on that time with a mix of anger and resignation. He knows that the skit didn’t completely destroy his career – after all, he did find some success – but it certainly stunted his growth and forever altered the trajectory of his music career.
“I’m a legend now,” he said with a bitter smile. “But back then, that joke burned my career to the ground.” And in that moment, as the pain and frustration of those years washed over him once again, Dylan couldn’t help but wonder what could have been if it weren’t for that one fateful skit on Chappelle’s Show.
Watch the full interview below:
