It's 9 p.m. on a Friday night in New York City and 2 Chainz, arguably the biggest name in Southern rap at the moment, is at an improv comedy show. Riding high off a performance of his Pharrell-assisted hit single "Feds Watching" on Jimmy Kimmel Live and on the verge of releasing his latest punchline-filled opus, B.O.A.T.S. II: Me Time, the rapper formerly known as Tity Boi waits in a tiny green room behind a thick black curtain at the UCB East Theatre. Earlier in the week, he cancelled a September 15 performance at the Williamsburg Park in Brooklyn, but he made it to an improv show next to a pizza place because of one man: Luis Diaz, a.k.a. Cipha Sounds.

The Hot 97 morning show host, DJ and stand-up comedian is on a mission. Through Take It Personal, his weekly hip-hop themed improv show at UCB East, he wants to explore the connection between the art of rap and the world of improvisational comedy. He begins each show by saying that the two have always had a lot in common but that the powers that be have kept them separate for too long. He's here to bring them together.

The correlation between improv and rap is nothing new, particularly at UCB. Donald Glover, a.k.a. Childish Gambino, studied and performed at the theatre in New York back in his NYU and 30 Rock days, and in 2011 Diddy appeared as a guest on The Chris Gethard Show.

"Improv has helped me in life," Cipha explains the morning of the 2 Chainz show at the Hot 97 studios. "I used to be very shy. I used to be kinda antisocial. At work I was always good, but personally I was kinda weird. It opened me up...Honestly, it's even helped my relationship. You just get better at rolling with things."

Though he performed stand-up comedy for years and served as the DJ on Comedy Central's Chapelle's Show, Cipha first became interested in improv when a producer at Hot 97 dragged him along to a show at the UCB Theatre in Chelsea in June of 2011. He went on Harold Night—the Harold is a longform improv structure that Cipha compares to MCing and DJing in a park—and he was hooked. "Just mainline, heroin to the fucking brain," he says.

Cipha became obsessed, enrolling in classes at UCB and attending shows. Despite his love for the form and for the UCB Theatre in particular, he realized that there was a gap between the rap world he spent his days in and the comedy world he was exploring at night. "Everybody on the radio was making fun of me 'cause improv and UCB is a very White art form," he says. "A very college, liberal, White community."

With the twin goals of making the community more diverse and scoring some valuable stage time for himself, Cipha came up with the idea for Take It Personal, which begins with Cipha interviewing the guest for the night on stage, typically a rapper or producer, and coaxing a longer story or monologue out of them, which a team of improvisors will then use as inspiration for a series of made-up scenes. Past guests have included a mix of hot newcomers (Action Bronson, Trinidad Jame$) and seasoned veterans (Raekwon, Prodigy), but he's never had a guest as big as 2 Chainz.

Though 2 Chainz is a very funny rapper, he's not exactly a typical guest at a theatre that hosts shows with titles like Improv Nerds, AIRWOLF and LASERS IN THE JUNGLE. And with his wildly busy schedule of appearances—not to mention the the fickle habits of super-star celebrities—he was a very difficult get for even someone as connected and respected as Cipha. With the show on Friday, 2 Chainz didn't confirm he'd be there until Thursday.