Jensen Karp’s Kanye West Owes Me $300 is a triumphantly funny look at failure

Silly Little Show-Biz Book Club is Nathan Rabin’s ongoing exploration of books involving show business, with a special emphasis on the very bad and the very sleazy.

In Kanye West Owes Me $300: And Other True Stories From A White Rapper Who Almost Made It Big, Jensen Karp emerges as something of a Zelig figure, and not just because he was the MC most likely to quote Annie Hall during his brief yet incredibly dramatic career as battle rapper Hot Karl. He was there when a feverishly ambitious producer named Kanye West was compared to Urkel because of his guileless enthusiasm and nerdiness. He was there when West played “Jesus Walks” for the powerful people he hoped could fulfill his dream of becoming a rapper, resulting in those assembled laughing derisively.

Karp was also there when fellow Interscope artist Will.I.Am floundered to such a degree that he briefly hitched his wagon to Karp’s temporarily rising star in a desperate attempt to keep from getting dropped along with his group Black Eyed Peas. Even more fascinatingly—and embarrassingly—the future superstar was so broke he’d hang around recording studios for the free food, pretending to be part of sessions he had nothing to do with. Karp’s 21st birthday somehow devolved into a drunken bacchanal that involved his buddy Mark McGrath waking up with a Virgin Mary neck tattoo despite not being remotely religious.

When the “Latin invasion” overtook the music industry at the turn of the millennium, Karp was there to cash in with “Caliente Karlito,” a would-be smash single. It was reworked by no less than Timbaland, one of a number of huge names eager to help themselves to the enormous “open budget” on Karp’s scotched major-label debut. Heck, when Latin hip-hop lothario-turned-respected A&R Gerardo wanted to come back, Karp was right there to serve as his hype man and ghostwriter. That last story isn’t important in any conceivable way, but it’s still pretty awesome to hip-hop geeks of my generation.

Most importantly, and disastrously, Karp was a white kid and a battle-rap-honed freestyle fanatic with a love of dark comedy and smartass pop culture references—at the same time fellow Interscope artist Eminem was becoming the biggest and most controversial rapper alive. The success of Eminem seemingly created a lane for other funny, idiosyncratic white rappers who didn’t fit the mold. Karp didn’t realize until too late that Eminem’s success would also close that lane. The man who would have made Hot Karl (Karp’s literally shitty stage name, and one he deeply regrets) a household name was Interscope kingpin Jimmy Iovine, who not coincidentally introduced Marshall Mathers to the world. Iovine shows up several times in Kanye West Owes Me $300—first in his capacity as a dream- and star-maker, and then in his equally notorious capacity as a dream-killer (and finally in an equally inevitable role of dream-forgetter).

But before everything went horribly, entertainingly awry, Karp was a nerdy, bespectacled kid from the not-so-mean streets of Calabasas, California. His parents were, if anything, overly supportive of their son’s dreams (to the point where his mom sometimes served as his hype woman and onstage dancer). From the very beginning, Karp was keenly attuned to the cultural zeitgeist and understood that even talented rappers benefited from a gimmick, or two, or three. As Karp wryly recounts in Kanye West Owes Me $300, he first achieved modest success as a preteen rapper and part of an interracial group whose standout track was a dis song to the more popular prepubescent hip-hop outfit Another Bad Creation. In it, Karp coldly alluded to having fucked Iesha, the girl ABC dreamily sang about pursuing in one of its hit singles. You’re never too young to internalize hip-hop’s innate sexism.

After nearly hooking up with Ice-T’s crew as a middle schooler, Karp reinvented himself as a battle rapper, a champion of both the lunchroom and later an influential radio program where Karp racked up victory after victory over unseen challengers while maintaining a crazy secret life. As far as his classmates were concerned, Karp was just a college student and Flintstones In Viva Rock Vegas crew member. But when he’d call the radio station that would become his early creative home, he would morph into a ferocious battle rapper, a freestyler whose incontestable skill belied his goofball appearance.

On one level, battle rapping represents a form of linguistic magic. It’s a harsh realm where rappers launch devastating verbal attacks in the moment, using everything at their disposal to improvise scathing insults. On another level, battle rapping can be something of a glib party trick, and one that reaches often and enthusiastically into a deep, fetid pool of homophobia. Sadly, like many successful battle rappers of his era, Karp wasn’t shy about tapping into this toxic line of discourse, and is appropriately ashamed of it, while acknowledging that a battle rapper in the late 1990s who eschewed homophobic disses completely had about as much chance of winning a battle as a one-armed boxer would a heavyweight title fight.

Karp looks back on his past with a combination of richly merited pride and equally merited mortification. Like Eminem, Karp peppered his lyrics with pop culture references so timely that they were doomed to be instantly dated. “Dated” is almost invariably used pejoratively, but Kanye West Owes Me $300 is dated in the best possible way. For hip-hop fans of my generation, it hits all the nostalgia sweet spots.

Karp includes the lyrics to his most significant songs as well as the ages that he wrote them in the book (he was 20 and 21 when his rap career almost happened). In another context, this might seem arrogant, but it works here, in part because Karp is more interested in analyzing his early work from the perspective of a grown man looking back at his adolescent mistakes rather than glibly celebrating his words. The lyrics Karp includes in the book are compelling primarily for what they say about Karp’s mind when he came achingly close to making it big.

It bears reminding that Karp was 20 years old, for the most part, when he nearly became famous. Even the most grounded, talented, and intelligent 20-year-olds are essentially just kids, and liable to make the kind of mistakes kids make. And also, just to be stupid, shithead little motherfuckers. Shit, I was 21 when I started writing for The A.V. Club, and at that point, I could barely read, let alone write well.

Karp was actually far less of a shithead than a lot of kids his age, and definitely for people who achieved so much, so young. Kanye West Owes Me $300 is not the story of a stupid kid who fucked up the chance of a lifetime by doing drugs, hitting the bottle, or generally devolving into a monster of id and ego. No, Karp kept his head down, worked on his craft, and did everything he could to transform his Interscope deal into a sustainable career. But sometimes people do everything right and end up taking a giant L all the same. But in every surreal encounter with a pop culture heavyweight, this born storyteller got an anecdote that almost makes all that failure and crushing disappointment worth it.

Karp never got to collaborate with Wu-Tang super genius RZA, for example, but he did have an exquisitely unlikely conversation with the eccentric artist in which RZA, trying to get a handle on Karp’s unique hip-hop persona, asks him if he’s a rap Richie Cunningham. When Karp replies that he’s not quite as square as Ron Howard’s squeaky-clean teen, RZA responds by asking if he’s more of a Fonzie type. When Karp says that he’s considerably less cool than the Fonz, if cooler than Richie Cunningham, RZA splits the difference and asks him if he’s a hip-hop Potsie, and Karp concedes that that’s probably the most accurate comparison.

Confessions Of A Hip-Hop Potsie would actually be a pretty great alternate title for the book, and one keeping with Karp’s sense of humor, but Kanye West Owes Me $300 is more than just a catchy title. Karp has a gift for crafting portraits of hip-hop stars that are as funny and revealing as they are succinct, and his take on a pre-fame West is funny but also, like much of the rest of the book, surprisingly emotional and poignant.

Phonte (whose longtime Little Brother producer 9th Wonder produced “I’ve Heard,” perhaps Karp’s best song) rapped that money doesn’t change you; it just makes you more of what you already are. On that note, it’s clear that even when West was living with his mom in New Jersey—volunteering that he was also a rapper to people who just wanted his damn beat CD and embarrassing himself by rapping at mortified waitresses whether they wanted him to or not—he was the deranged, attention-crazed narcissist he would become in embryonic form. It just took money and fame and power to kill the humble kid who always showed up early for recording sessions despite living in the middle of nowhere and give birth to the superstar seemingly perpetually in the grips of a very public nervous breakdown. West and Karp have a bit of an A Star Is Born dynamic: As the once white-hot Karp plummets to the ground, the nerdy kid unexpectedly rockets to stardom as a rapper-producer.

Kanye West Owes Me $300 reminds me of another book I’ve covered for this column about a ferociously talented iconoclast who almost made it: J-Zone’s Root For The Villain. It’s tempting to say that Zone and Karp are too smart for hip-hop, but it’d be more accurate to say that they’re too smart and principled for the abundant bullshit that comes with being a hip-hop recording artist. And I’m pleased that after retiring from hip-hop in disgust, both artists have cautiously returned to the genre, albeit on their own terms: Zone with a pair of rock-solid comeback albums and Karp in a more modest way, with some new music on his website.

Karp starts to lose his shit when he’s dropped from Interscope, possibly at the behest of someone in Eminem’s organization. He ends up going the independent route with his 2005 debut, The Great Escape, which I apparently reviewed here at The A.V. Club, something I forgot about completely until Karp reminded me of it when I met him at the Gathering Of The Juggalos last year. (He was there backing up and performing with Nova Rockafeller, a white female rapper he manages.) Needless, to say, Karp’s life has not gotten less interesting since he left rap, seemingly for good. He owns pop culture galleries and a pin company, has his own Earwolf podcast, and is brilliant at Twitter, a medium that allows him to tap into the skills and quick wit he honed in his precocious battle rap days.

In the section of my review of The Great Escape that Karp quotes in his book, I write that “Karl’s creative soul might not be worth the hassle,” a fairly brutal and heartless assertion (Jesus, it’s easy to be a cold-hearted fuck when you think you’ll never encounter the people you write about) he surprisingly agrees with. I would now like to take the time to say that Karp’s creative soul is most assuredly worth the hassle. It just took a different medium for him to fulfill his enormous potential. He took his overhyped nothing of a rap career and transformed it into the basis of a book that is something special. If that isn’t hip-hop, I don’t know what is.