Dylan Dili Says Dave Chappelle’s ‘Top 5’ Skit Hurt His Music Career

Dylan Dili from Making The Band 2 wasn’t laughing alongside fans when Dave Chappelle debuted his iconic “Top 5” skit, which poked fun at his appearance and larger-than-life personality on the popular reality TV series.

During an interview with We Are Flatbush published March 1, Dili opened up about the negative impact that Chappelle’s skit had on his career. According to the radio host and entrepreneur, the comedian’s legendary “Top 5” skit, where he famously mocked his mannerisms on Season 2 of The Chappelle Show, damaged his reputation with record labels and promoters.

“Any time I send my music to DJs, they say, ‘Oh, that’s the nigga that Dave Chappelle made fun of, nah, I’m good on that,’” Dylan revealed. “Not only that, but now, every promoter says, ‘Nah, we’re not booking him.’ So now I have a newborn, and the fridge is empty in 2005, and no one is calling me. Everyone is laughing.”

Then, the Flatbush native got emotional when he recalled contacting several labels, only to be met with no follow-up or get turned down by record execs.

“I’m a legend now! But [back then] I’m fucked up for what you just did. And you’re not answering the phone. At that time, no one picking up they phone. Not one label, and at that time, you had to sign to a record label. So, I’m calling them direct. And they said, ‘I can’t help you.’ That joke gone, boy. That joke took over. That joke burned it.”

The emcee – who hails from Grenada – wanted to fight people who would recite Chappelle’s iconic “Dylan, Dylan, Dylan” quote from the skit.

“It wasn’t funny anymore. At that time, I remember wanting to fight because I was hurt. I’m not making no money from this. It really burned me,” he told the We Are Flatbush interviewers about the painful aftermath of the iconic Chappelle Show skit.

Over the years, the Caribbean artist claimed that he tried to reach out to Chappelle, but the comedian never contacted him back. In 2018, Dylan finally met the actor and stand-up comic at his show in Brooklyn. Surprisingly, their interaction was cordial.

“I said, ‘Dave, you made me famous.’ And Dave said, ‘N—a, you made me famous. I wasn’t hot until that shit…What we drinking on? Take a shot, pull up.’”

It turns out Chappelle’s grandmother is from Grenada, which inspired him to poke fun at the rapper.

He said, ‘I had to make fun of you, n—a. I know the culture.”

Following their friendly meeting, Chappelle assured Dylan they would stay in touch. However, his calls went unanswered whenever the rapper attempted to reach out.

Eventually, Dylan was able to capitalize on the success of the skit.

In 2021, he released a craft beer called Top 5, the only IPA craft beer that has sorrel in it, according to Dylan.

“I’m the number one craft beer in Atlanta. Now, we’re going national in 2024,” he gushed during his We Are Flatbush appearance.

He also has a weekly show on iHeartRadio’s FUBU Radio.

“My show is called The Top 5 Show. I merchandised the Top 5 – and you know I had to do that because…these are words I never said. I never created. I never put this out. I had to trademark it and go through fights to trademark it,” Dylan explained.

What was Making The Band 2?

Making The Band 2 was a reality television series aired on MTV from 2002 to 2004. The show followed music mogul Sean “Diddy” Combs as he searched for talent to form a hip-hop group. The first season focused on creating the rap group Da Band while subsequent seasons followed different iterations of the group as they worked on albums and navigated the music industry. Dylan was one of the members of Da Band featured prominently on the show.

Known for his rebellious attitude and bold personality, Dylan stood out among the group. However, his independence and differences in opinion sometimes led to criticism and pushback from others. After Da Band disbanded in 2004, Dylan inked a deal on Akon’s Konvict Music for his album Pain 2 Power.

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