Following the lead of hip-hop’s warm embrace of comedy—from rappers’ enthusiastic references of bits from comics like Eddie Murphy, Katt Williams, Dave Chappelle and Kevin Hart, to hip-hop/comedy fusion shows like Def Comedy Jam—Nick Cannon capitalized on the early 2000s with his hilarious live battle show Wild 'N Out. The show, which ran from 2005-2009 on MTV, was a staple for hip-hop audiences, in large part because of special guest appearances by the game’s biggest rappers, who would come on to freestyle battle and show off their comedy chops before performing for the studio audience at the end of the show. It was always a party, but after four years on the air, Cannon hung up the comedy mic for endeavors like America’s Got Talent and his radio show on 92.3 NOW.

Now, after a five-year hiatus, the always-busy Cannon has partnered with the more youth-centric MTV2 network to bring back Wild 'N Out, but this time it’ll be a bit different. In watching the first few episodes, it’s clear that the new season will be a bit edgier and more in-your-face, but don’t get us wrong—it still looks as fun as ever.

In anticipation of the July 9th premiere of the new season, XXL has partnered with MTV2 to bring you a series of interviews with standout cast-members from the show. For our first installment, we spoke to New York battle rapper Conceited, which you can find here. This time around, we talked to improv comic Jacob Williams, who has a surprising history with Cannon. In a phone conversation with Williams (who was in Chicago at the time), he told us about his improv education, getting to meet some of his favorite musicians on the show and how he performed with Nick Cannon while still in college.

XXL: Tell me about your background in comedy and improv.

Jacob Williams: I've been doing stand up comedy [for] six years now. I started in college and I’ve gotten to do a lot of improv at places like Second City. I'd always been a fan of comedy growing up, but have only been doing stand up and improv for a few years, so doing a show like this was kind of a perfect opportunity because it brought so many different things that I like together.

Did you watch the original show when it was on MTV?

Yeah, I used to watch the show, and I always thought just seemed like the most fun job to have. I always thought there was a really good vibe on the show, and that people seemed to really get along. And the audiences were always great.

Is there a writing process for the show, or is it all improvised? 

It's pretty much improvised. Sometimes for certain games, I might have a minute or two before it's my turn to go, but for the most part it's all made up on the spot. And you never know what can happen, because everyone is bringing different ideas. There's something really cool about doing improv on the spot.

So Wild 'N Out is famous for bringing out hip-hop acts for the show and for performances afterward. Were you a hip-hop fan growing up? 

I listen to hip-hop. I listen to a lot of different music, but it was pretty exciting to see some of the guests that came on and everything. But yeah, I definitely listen to a lot of hip-hop. And on this show, there were all these guys who make songs that I listen to on the radio and stuff so, yeah, it was very surreal to meet some of those artists and actually be on stage while they're performing their hit songs.

Nick Cannon - "Can I Live" (2005)

You mentioned that you trained at Second City in Chicago. Did you have any hesitation, going from a classical improv background to Wild 'N Out, which has more of an urban audience?

I think that improv comedy is a universal language. When I was going into the show, it was definitely surreal, but I was really excited about it because my roommate runs a show that’s a lot like Wild 'N Out, so I figured I had good practice. I also think that I have a really unique style, especially in this context. But I really think this is some of the most fun improv and comedy that I’ve done, and it was cool because I got to do things that I hadn’t done before, like battle rapping and stuff like that.

How did Nick Cannon find you and invite you to be a part of the show? 

I actually met Nick a few years ago. When I was in college, at one point I was very obsessed with comedy and I was a fan of Nick’s, so I entered this stand up comedy contest where you submit a video of yourself performing. And I guess it was a national contest to open up for Nick Cannon when he filmed his special in Las Vegas. Somehow I ended up winning that, and at the time it was surreal to get flown out and get to meet him and actually do stand up in Vegas. He was super nice and really funny, and it was cool to meet him. Then the next year, I sent in a video to America’s Got Talent (which Nick Cannon hosts) and actually made it through a few rounds. I saw him there, and I assume from that, he thought of me for Wild 'N Out. That’s how I got the first audition, then luckily I got called back to be on the show.

Assuming there will be a Season 2, would you do it?

Yeah, absolutely. Doing this season was probably the most fun I’ve ever had. There was just so much going on in a short amount of time, that it was like a whirlwind. So yeah, I’d definitely go back if they had another season.