Back in 1999, Jensen Karp was a rap-obsessed 19-year-old USC student who had no thought of a music career. He was white (back when white rappers were still a rarity), took as much influence from Don Rickles one-liners as from Ice Cube’s street tales, and hailed not from Compton or Queensbridge, but instead from an L.A. suburb just outside Calabasas. All told, he was about as far from that era’s idea of a popular rapper as you could get.

But he loved battle rapping, so when the opportunity came that year to battle on an L.A. radio institution, the Roll Call, Karp jumped at the chance—using a name he swears he made up on the spot, Hot Karl. He called in to the station to battle another listener on the other end of the phone. And he won. And won again. And won again. After a record-smashing 45 consecutive wins, Karp walked away and signed a million-dollar record deal with Interscope.

Hot Karl recorded an album with guest spots from Fabolous, Redman, Mya,, and the dude from Sugar Ray (hey, it was 2000). He also got a beat from a then-unknown producer he'd befriended named Kanye West. 

But as you might remember, Interscope had another popular white rapper at the time, so the Hot Karl album was shelved, and Jensen Karp moved on to other pursuits. He looked back on his rap life in the 2016 memoir Kanye West Owes Me $300: And Other True Stories from a White Rapper Who Almost Made It Big.

The newest chapter in Karp’s life brings him full circle, back to battle rap. He’s the executive producer and one of the writers for Drop the Mic, the TBS show (spun off of a popular segment on The Late Late Show With James Corden) where celebrities battle each other on the mic. Battles over the show’s two seasons have included Atlanta’s Brian Tyree Henry going up against David Arquette, Liam Payne vs. Jason Derulo,  Shawn Mendes battling line-for-line with Odell Beckham Jr, and the memorable, Black Sheep-interpolating matchup of Seth Rogen and Joseph Gordon-Levitt

The battles are funny, pointed, and well-written and delivered, with an obvious love for the art of battle rap. Complex talked to Karp to find out how he got from battling anonymous radio listeners to penning insults for the biggest celebrities in entertainment. 

I know a bit about your rap background from your book, but I’m not quite sure how you got from there to here. How did you get started writing comic raps for celebrities? That’s kind of a strange niche.
After the Interscope deal fell through, I had one of those moments—it’s been chronicled by me and guys like J-Zone—where you’re like, I don’t know if I can continue to be a professional rapper just because I financially have to live. I looked at other people I had come up with that continued to rap past their deal or past their buzz, and I just couldn’t see myself doing that. So I sat back and tried to figure out, without being too hard on myself, what it is that I wanted to do next.

Now that it’s kind of worked, it sounds like a very logical thing to do, but it’s not. “What do I do next?” is a really hard thing to say. Especially with a million-dollar deal like I had, I didn’t expect it to end that way. It felt against every instinct I had to continue to rap. I had a bunch of dough from the Interscope deal and from my publishing deal, and I graduated college during recording the album. Film writing and journalism were my majors. I had been doing stand-up off and on throughout my entire college career. I had been going up at open mics and with no real focus or reason to do it other than I loved writing jokes.

After the record deal ended, you opened up an art gallery. How did that lead to the next phase of your career?
Twitter was created around that time, so I was writing jokes on Twitter. I worked for Damon Lindelof and Carlton Cuse [co-showrunners of Lost] a little bit, based on them liking what we were doing in the gallery. Damon and a comedian named Paul Scheer who everyone knows, I had worked with both of them on some Lost marketing stuff. They saw what I was writing for that and on Twitter and just jokes in my own life, and both those dudes pushed me to take it further. So I started getting called into writers rooms for brainstorming.

I started to get booked up for award shows and different writers rooms, and from there I started working every month on different comedy shows. I started to act a little, and moving along, and Hot Karl’s way in the back. It didn’t even come up in most of these jobs. Then I got a book deal and optioned that book. It was like an avalanche—it sort of kept rolling and rolling. One of my stops was the MTV Movie Awards hosted by Kevin Hart and The Rock.

And that was where we got the rap about The Revenant that went viral. How did that happen?
They wanted a music moment, and I had already written with Drake on the ESPY Awards a couple years before. Word got out that I helped him with some music comedy stuff, so they called me in. I wrote this song called “Leo Got Fucked By a Bear.” I wrote that in like an hour. [Laughs]. It just spurted out of me. The Rock and Kevin loved it. We filmed it and I taught them how to rap. I mean, Kevin kind of knows, but The Rock had no idea. So I taught them and that went viral the next day. My agent was like, “Do you have any ideas that involve rap?”

For years, I had wanted celebrities to rap battle against each other. I wanted to teach them and write it and show that anyone can do it if they really focus on it. So I went in and pitched James Corden and Ben Winston, his partner. James believed in it basically from the minute I pitched it. They had never seen rap battles, so I showed them King of the Dot and Smack and all the things that I’m obsessed with, and they loved it. They totally got it. They pointed to the board and said, pick a celebrity you think can do it and they’ll battle James. I picked Anne Hathaway, and they were like, there’s no way she’ll do it. We called Anne Hathaway and she was in minute one. When she came out to do it, I knew we were onto something.

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The next day David Schwimmer was booked to appear on Corden. He saw the Anne Hathaway bit, called in and said he wanted to do it. He wrote his own lyrics. He was incredible. Then TBS was already interested in turning it into its own show.

What was Drake like to work with? Could you tell that he had acting experience in addition to rapping?
Oh yeah. I’m a Drake fanatic. I love the music—which I guess makes me less of a hip-hop purist—but I also just think he’s great, and working with him did not help me in that because he’s incredible. [Laughs]. He’s insanely talented, so funny. 

At the ESPYS, you accidentally started beef between him and Macklemore?
I wrote this joke for Drake. We had this song that was for second place [“Honorable Mention”]. Like, everyone celebrates the champions, but what about second place? There’s a lot of easy Danica Patrick jokes and all these things in it. One of the lines we had written was, “The winners don’t always deserve it, just look at the Grammys,” because that was the year that Macklemore beat Kendrick.

I had written that, but I don’t think Drake really knew why I wrote it. I don’t think he knew it was because of Macklemore. So as a joke during rehearsal, I had them put up a picture of Macklemore behind him when he said that. Everyone laughed, and he just looked directly at me and was like, “That’s your joke.” [Laughs]. I was like, yeah, and he kept it. He loved it and it went on air, and the next day Complex wrote an article that was like, is there beef between Drake and Macklemore? I was like, that’s because some idiot writer made him put up a picture.

You’ve said you can teach anyone how to rap in two hours. You and your team have to do that every episode on Drop the Mic. How do you do it?
Well number one, they have to come in with like a respect for the art form. It sounds very easy, but it’s not. We have to have a celebrity who understands that this is not a joke. We’re not having you come out in a sideways hat and gold chains and gold teeth. That’s outdated and stupid. What we want you to do is be yourself.

this is not a joke. We’re not having you come out in a sideways hat and gold chains and gold teeth. That’s outdated and stupid. What we want you to do is be yourself.

I was a battle rapper my whole life. Around six to eight years ago when battle rap took that turn and became about writing and not freestyling, guys like Rone and Dizaster and Pat Stay and Hollow da Don, a lot of these dudes that I was really becoming a fan of, showed that it was about the writing and the delivery. You’re not Canibus out there. You’re not Pharoahe Monch. You don’t have to be the best rapper we’ve ever heard. You have to swagger and deliver it correctly.

The actors who appear on Drop the Mic usually kill it. Why?
With battle rap, actors actually connect with it pretty easily because it’s a lot like theater in a way—and not shitty Hamilton. I mean, it’s just finding your hits, finding where the metronome would be. So I knew that someone like Anne Hathaway who had done Broadway and musicals before could find that niche. For The Rock for example, it’s about listening to it and doing it the same way he would learn lines for a movie—learning the cadence and really feeling it and knowing the tradition of battle rap, not just going out there and being a goon. We have coaches that come in, including myself and a lot of battle rappers, and actually show them how they do it. So listen and respect it. We’re not asking you to drop a mixtape the next day. We’re asking you to go out there and have a fun comedy sketch. It’s paid off in a lot of ways.

Do the contestants know what the other person is going to say about them before the taping?
Not really. We don’t want anyone to be uncomfortable so we talk to them about what is and what isn’t off limits. But most of the off limits is stuff that we would never talk about. Like, it’s so crazy when someone’s like, “Yeah, I’m not really interested in talking about my divorce.” And you’re like, neither am I. [Laughs]. And then Halle Berry was like, “Please talk about my divorce,” which was nuts.

But when we talked to Mayim Bialik, I was like, here’s some of the things we’re gonna hit and she was like, “Did you hit my nose?” I was like, no. And she was like, please make fun of it. So they have an idea but they don’t [know their opponent’s exact lines].

Has anyone ever actually gotten mad?
No, I don’t think so. I think if you watch the Jay Pharoah/Marlon Wayans one that we aired like two weeks ago…

That's what I was going to ask about. Jay accuses Marlon of stealing a joke, which in comedy is a huge deal.
Yeah. I know nothing about the backstory other than what you heard, but I know that it’s real. I didn’t expect that reaction. It happened and then we had to send Method Man up, which was nuts. In the end, they were fine. 

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Anyone who sees that and like questions our hip-hop credibility or what we’re doing, it’s like, dude, like I read a story the other day about how Celine Dion’s son is the number one rapper on SoundCloud and I hear Lil Xan talking about how he hates Tupac and I see XXXtentacion releasing a good record and hitting women in the head. We’re the last thing you should be mad about in hip-hop. We’re at least going out there and respecting the art form and if you watch the Jay Pharoah/Marlon one or Seth Rogen versus Joseph Gordon-Levitt, if you watch any of those, you’re gonna be like, this might be the only boom-bap rap on television.

You had this career as a rapper that got cut short before it could really get started. Now you’re back writing raps, albeit in a very different context. How do you feel about that?
It’s a really good feeling. I mean, it’s crazy. Even just to think I’m still making a living off writing lyrics compared to my contemporaries and people that I came up with. Out of everyone who rapped with me in 2000, there’s not many that are still [rapping]. Those guys are legends that are still around. There’s only a handful, really. 

I think the cool part is, I failed in that realm. I failed and hit a dead end but I wasn’t willing to give it up. So I  made a U-turn and found a different way in to still satisfy my own creative desires and I was lucky enough to be able to do that. That I’m really thrilled about, yeah.

You’ve said that back when you were working with him around 2000, Kanye had signatures in his two-way pager messages that had four album titles and years—none of which had been released yet. How close did that come to being accurate?
It’s almost exact. He just didn’t do Good Ass Job.

But he had The College Dropout, Late Registration, and Graduation?
Yup. Everything’s the same. Same order. He got the years very close. I don’t know if he hit it exactly, but he definitely got the time in between perfect. He’s a savant in so many ways but that one is almost the most terrifying one. He’s that guy. He has always been that guy. He’s just a determined weirdo.

Kanye has always been that guy. he's just a determined weirdo.

When you think back on the Kanye you knew and look at the guy we see today, what’s most surprising about him now, and what doesn’t surprise you?
What doesn’t surprise me is that when he has his ego hurt, he reacts. I talk about it in the book a lot. He would rap for us. He would act it out and stand on a table and do these things, and he would leave the room and we would all laugh. When I say “we,” I mean I was the least important person in hip-hop in the room. There were very, very famous people in those rooms that would later go on to work with him.

I know what he faced in that way, and I know that the reason he would never stop saying “No one believed in me” is because that’s a huge deal to Kanye West. He would tell people, “I’m the next Michael Jackson” even when he was being told by his managers, “Please don’t say you’re a rapper.” They thought it was weird when you would go into a session, spend $10,000 on a beat from him and then he’s telling you, these are not my best beats. And you’re like, why did I just pay you ten grand? Everyone knew his beats were incredible. That’s not a question. We didn’t think he was that good of a rapper, and he believed differently—and he was right. I mean, to my credit, he got a lot better.

What did you think of the Charlamagne interview?
When he talked about how Obama called him a jackass, that resonated so much. I was like, oh, that’s why this Trump thing is happening. It almost plugged in immediately—he thinks this is that. He thinks he’s pulling one over on Obama who didn’t treat him right, and that’s kind of what his rap career has been.

People always make jokes about when Eminem or Kanye talk about their haters. They’re like, who are your haters? You’re the biggest rapper in the world. But the haters are the people they’re thinking about on day one: the people from the Hip-Hop Shop in Detroit or the L.A. Rap Olympics for Eminem. They’re still using those people as their motivation. Kanye is just the most absurd at it, and that doesn’t shock me.

What surprises you about Kanye today?
We talked about his mother a lot. He talked about his mother being an activist and all these things. Politically, when he did the George Bush doesn’t care about black people, that charts for me. Like, oh yeah, that’s Kanye West. That was what I knew about him. But this [supporting Trump], it’s anti-everything he had told me politically or anti-everything that he said his mother stood for.

The other thing is that movies don’t come up a lot in Kanye West’s career. He was obsessive about film. He tried to see everything. He loved talking about movies. It’s like almost what he does for fashion now, but he had done that for movies. No one talks about that.

I once saw his HBO pilot. It wasn’t that great.
Yeah, and I think that might be the reason. I think that the Larry Charles thing and then Anchorman—doesn't he have a small part in one of the Anchormans or something? I think he just isn’t good at it and he realized that pretty fast.

The Wu-Tang Clan first came out when you were in your prime rap-listening days. What is it like now to have Method Man as a coworker?
It’s crazy. As a coworker? Jesus Christ, I’m his boss. It’s literally insane.

He is my hero. People who went to high school with me think it’s the craziest thing of all time. For my first car when I was 16, I went to the swap meet near my house and had his logo airbrushed on the front license plate. I’m fanatical about this and I had to pretend I’m not for a long time, but him and Ice Cube are my two favorite rappers of all time. I mean, he’s the only solo artist to ever have a song with Biggie and 2Pac. He’s been on Inside Amy Schumer but also worked with Jim Jarmusch, so it’s just a career of insanity.

He’s an incredible talent and I’m so happy to give him a mainstream gig where he can still do all of his critically acclaimed movies at the same time. I want the world to know how fun he is and how great he is. James and Ben knew Wu-Tang, but they didn’t know the individual members because they’re not hip-hop heads and they grew up in the U.K. But it took two minutes for James to meet him and go, “This guy’s a star.”

We’ve been talking about battle rapping for a while now. Would you be willing to give it a shot with me?
To make fun of you? Yeah, okay, let me think. Let me think. Alright, hold on:

[NOTE: Click on the video below to hear Jensen's diss of writer Shawn Setaro.]

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When I was told I was interviewing with Complex, I thought it was dumb
’Cause it wasn’t Sean Evans and this isn’t ‘Hot Ones’ 
Listen, you work at Complex, I hope you’re recording 
Let me guess: You’re a white guy who likes streetwear and Jordans
And when I think of your website I think it’s Hypebeast lite
But listen to ‘Drop The Mic,’ TBS Sunday nights.