'Kanye West Owes Me $300': Jensen Karp on his 'ridiculous' rap career

Today’s music industry may be uncertain as ever, but back in 1999, there was only one surefire way to the top: a record deal with one of Hollywood’s finest. At 20 years old, Jensen Karp was closer than most can dream, leveraging a radio contest win into a million dollar contract with Interscope Records.

Under the stage name Hot Karl, Karp shot from suburban SoCal teen to hip-hop breakout, clinging to his burgeoning fame with wide eyes and a silver tongue—that is, until it all went sour. In his new book, Kanye West Owes Me $300, Karp recounts his wild ride toward stardom and its crashing demise, shifting through absurd encounters with the likes of Kanye West, Sisqó, and will.i.am.

“It’s a fish-out-of-water tale about me being very involved in this hip-hop history as an outsider, like being there when Kanye first played his music for other people or writing an R&B song with Sisqó,” Karp tells EW. “Very weird things for a kid that looked like a rapper’s accountant.”

Despite his failed venture as an early ‘00s rapper, Karp’s since repurposed the career that made him (almost) famous, launching a Los Angeles art gallery, hosting podcasts, and working on skits for big-time award shows like the VMAs and ESPYs.

“A lot of people allow a journey like that—one that has a sad ending—to define them, and I didn’t let it,” he says. “I just found other avenues to get my creativity out and not let someone else pen my story. It’s cliché, but I didn’t want someone else to write the final chapter. I wanted me to do it.”

For more on Kanye West Owes Me $300, EW spoke with Karp about stealing porn from Sisqó’s home, Kanye’s clairvoyant two-way pages, and rebuilding after a failed dream.

Last time we talked, you told me about the outrageous “Leo Got F—ed by a Bear” song you penned for the MTV Movie Awards. Was your rap style always comedic?

Yeah, definitely. My history was always that I would listen to a Run DMC album as much as I would listen to a Steve Martin album. There was always a middle ground for it, and I was sort of ahead of the trend with being yourself in rap music. I never wanted to make a joke of it because technically I’m a good rapper. My aesthetic is funny and humorous and I write jokes—that’s what I do for a career—but at the same time I’m actually being a good rapper while doing it. My history in rap is pretty much the most ridiculous part of my life, and that’s what Hot Karl was—a weird project where I could let my influences seep through and not just change because I know what would sell better. I was just being myself. Even though it didn’t play out the way I really wanted it to, I still feel pretty good about it.

What can you tell me about the book?

It’s my story growing up in an affluent suburb—although my father was a car salesman so I didn’t really relate in that way—and I loved the art form of rap. I connected with it before any of my classmates did, and I was sort of ridiculed for loving it. I was at a high school that spawned Incubus and Hoobastank and Lincoln Park—it was more of a rock thing. But I continued to rap, and in college I entered a radio contest in Los Angeles. It was a battle thing. I’d go back and forth with two or three other rappers every day, and I ended up winning. The winner before me had 10 days of wins, and I had over 40. So I ended up being this L.A. radio phenomenon back in ’99.

Just as I was about to go to college, [Interscope Records co-founder] Jimmy Iovine offered me this million dollar record contract as a teenager. I ended up recording an album for them with Kanye West, will.i.am., Redman, DJ Quik—they basically gave me everything I wanted. It’s a fish-out-of-water tale about me being very involved in this hip-hop history as an outsider, like being there when Kanye first played his music for other people or writing an R&B song with Sisqó. Very weird things for a kid that looked like a rapper’s accountant. It was a surreal ride, and it doesn’t end with the happiest of endings. I sort of retired out of rap after I was told the label couldn’t release my album because of scheduling conflicts, which has a ton of controversy and weird conspiracy theories around it, but it tells that story up until the day I decided to never rap professionally again.

You have a lot of outlandish stories from along the way. Can you tease any of those?

One time I went to write an R&B song at Sisqó’s house, and when I went to the bathroom, I decided to steal porn from him. It’s a very weird story, but there are a million of those. I had my 21st birthday with [Sugar Ray’s] Mark McGrath at this swank, L.A. nightclub. He bought me a bottle of Cristal, and it ended with him getting a Virgin Mary neck tattoo that he’d later get removed. These things happened all the time, and I was always the person looking at it from afar like, “What is going on?”

I was one of Kanye’s first checks for production, before he even admitted he was a rapper to most people. I was an early stop on a very fast train. We went to movies together, we went record shopping together. I don’t know this person—it’s been 15 years—but I was able to see what a superstar is like before they have that opportunity. One crazy thing is that we used to have two-way pagers back in the day; all rappers had them. It was like texting before texting was a thing. Before people even knew he was a rapper—this is when he was still a producer—all of Kanye’s two-ways would say at the bottom, “Check out my albums,” and it would list all of his albums. It was all the titles he released 10 years later. They were all in order. The only one he didn’t do, is that after 808s & Heartbreak, he was going to do one called Good Ass Job. But all of the rest of them were in order, and I think even the years next to them were really close to when he released them.

When we’d go to restaurants together he’d say to the waitress, “Oh, I’m a rapper, do you want to hear me rap?” And she’d say no, but he’d do it anyway. Just watching a superstar come together and see someone who was destined for bigger things was a remarkable journey. We haven’t really spoken since his [2002 car] accident, but watching the prelude, the episode one for him, was worth a book in itself. But it’s just one chapter.

What did you learn from that journey?

The biggest thing I’ve taken away is that a lot of people allow a journey like that—one that has a sad ending—to define them, and I didn’t let it. It took a lot of work, but when I saw a dead end, my goal was to make a U-turn. It was a huge blow to me, especially at such a young age, to feel that failure, but I didn’t want to give up. So the thing I learned most from that journey is that there really is no dead end, you just have to make a U-turn and find another way in. I just found other avenues to get my creativity out and not let someone else pen my story. It’s cliché, but I didn’t want someone else to write the final chapter. I wanted me to do it.

Looking back, what’s your stance on the music industry?

It’s not for the weak. Being a 36-year-old man now, I look at it and I think I wish I was 36 when I signed a record deal, but who would sign a 36-year-old rapper? That sounds terrible. When you’re young and you’re trying to make it and you want people to hear your voice, you sort of don’t have a voice of your own. I think for people who are trying to push their music out there now, a point of view is so important. That’s what you see with so many big artists now—they create their own lane, and that’s what I wish I would’ve done. There’s no human way a 20-year-old who won a radio contest would have that kind of ability, but I wish I did, and that’s what I tell anyone who asks me advice from that time.

Kanye West Owes Me $300: And Other True Stories from a White Rapper Who Almost Made It Big is out now.