In 2004, Cipha was the official DJ of The Chappelle Show. After much encouragement from Chappelle and his radio listeners, Cipha took his first steps into the comedy world. Cipha was passed at the legendary Comedy Cellar in New York City, as a regular comedian and host. Soon after, he began touring with big names in comedy such as Chappelle, Aziz Ansari, Michelle Wolf, and was even featured in Michael Che’s Netflix special, Micheal Che Matters.