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Dave Chappelle meets all 5 of the greatest rappers alive

Photo: Ray Tamarra / Getty Images

Back in 2004, a parody of MTV’s Making The Band appeared on season two of Chappelle’s Show, and a much wider audience was introduced to the pure, untethered ego of a rapper who wasn’t afraid to spit hot fire. His name was Dylan.

Now, years later, the real life Dylan Dili finally got the chance to meet face-to-face with the comedian who portrayed him as a conceited, Wyclef Jean-choking lunatic. In a video posted to Twitter and Dylan’s Instagram, Dave Chappelle not only gave Dylan’s new solo album Pain 2 Power a free plug but resurrected a bit of the old act to remind fans who the five greatest rappers alive are.


In an interview with TMZ, Dylan gave a little insight into the not-so-chance meeting. Apparently, he’d been wanting to bury the hatchet for a long time, not just with Chappelle but with Diddy and the rest of his Making The Band cast mates as well. Understandably, the rapper is looking move on from the last decade of being a perceived as a parody of himself, but, for some reason, thought the best way to do that was to be seen with the guy who made that parody famous. When he heard Chappelle was at a nearby party, Dylan took the opportunity to “bum rush” him and capture this little moment on video. Luckily, Chappelle was a good sport about it, and comedy fans got to revisit one of their favorite bits.

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