If you’re a gambler, you’re in luck. If you’re looking for a fair fight, look elsewhere. This one’s a scorched-earth, Reagan ‘84-grade blowout. It’s also a story of the circuitous journey of intellectual property and the hazards and limitations of flattering yourself that you’ve created something new and exclusive under the sun.

He was an artistic and entrepreneurial pioneer in hip-hop but Ice-T was always less interesting as a rapper than he was as a public figure, which is in no way a dig. He was a capable MC, although, as the critic David Browne observed, his style could be better described as “intonation” than rapping. Along with Too $hort, he was one of the first to infuse hip-hop with the philosophy and aesthetics of the author Iceberg Slim and wrote a few classics (notably “6 ‘n the Mornin’” and “L.G.B.N.A.F.”). But as a public figure, he was absolutely essential to understanding the racial politics of the early ‘90s.

T’s journey took him from tanking his career with a poetic fantasy about slaughtering arrogant, closed-minded cops to playing an arrogant, closed-minded cop on Law and Order: SVU. His autobiography and essay collection The Ice Opinion: Who Gives a Fuck?, released realtively early in his career, sheds some light on how this transition was less about hypocrisy and opportunism than it was an example of the ontological fluidity that allowed him to succeed as a street hustler in Los Angeles, home of the most Machiavellian street hustlers in the world.

In 1993, though, Ice-T was at loose ends, and his desperation clouded his hallmark intelligence. He’d lost his representation and become a public pariah thanks to “Cop Killer,” an explosive track he recorded with his heavy metal side-project Body Count. 1993’s Home Invasion is a sprawling tribute to the scatterbrained loss of identity he experienced at the time, a mix of a few good ideas, a lot of tossed-off bullshit, and seething paranoia.

His “99 Problems” was an explicit attempt to return to the sex-rap he did better than most (particularly “The Girl Tried to Kill Me”). The aggro, high-impact track is one of the album’s sonic highlights, and Ice had the wisdom to bring on Brother Marquis from 2 Live Crew, who easily smokes him. Ice’s verses are a list-making, “99 Lines About 44 Women”-style catalog of the countless women who find his charms irresistible and whom he finds the time to spoil rotten, despite his overfilled dance card. It’s one of the better jams from a frustrating, overstuffed LP recorded at a lousy time in his life and career.

The song gave the world the line, “I got 99 problems and a bitch ain’t one,” but it left it to someone else to make that hot line a hot song.

In March 2001, the Miami shock-rapper Trick Daddy took a swing and missed. Trick’s “99 Problems” is essentially a cover version marked by its emotional and creative vacantness. Despite a decent beat and a few memorable jokes, it’s not in league with Ice’s version, or even with the best of Trick Daddy’s uneven catalog.

Later that year (on September 11, 2001, by pure coincidence, I’m sure), the New York rapper Jay-Z dropped The Blueprint, an escape from the wreckage of post-Biggie Smalls jiggy rap and a defiant, definitive statement of purpose that proved, among other things, that’s it’s possible for me to get an entire LP stuck in my head for the better part of a decade. After that, Jay-Z was welcome to spike the ball and do victory laps for the balance of his career. Instead, he released The Black Album, an even more challenging and satisfying tour de force and expression of his calculated, hot-and-cold, hyper-observant ethos.

Jay’s “99 Problems” is hardly about the bitches at all, focusing entirely on the problems. These range from the personal rendered with fist-pumping universality (the hostility of critics who refused to grok his artistic transformation) to those common to black men in America, rendered with horrifying specificity and detail (being pulled over and searched by arrogant, closed-minded cops). The track is a triumph of early-aughties hodgepodge aesthetics, and the vocal easily lent itself to detournment by the mashup artists ascendant at the time. Indeed, it’s such a brilliant, undeniable anthem that it’s been referenced everywhere from White House press conferences to cover versions by the likes of Courtney Love, the artistry of which made Trick Daddy sound like Nina Simone in comparison.

Jay’s version had little to do with Ice’s outside of the 100% recontextualized quotation, but of course Ice had to embarrass himself by getting salty about it, long past the end of his relevance in rap. Ice expressed chagrin that Jay never credited him with the concept, going so far as to remake his “99 Problems” with Body Count, which only served to highlight its limitations (and the fact that the best thing about it was the now-deceased Brother Marquis). Having made examples of Nas and Mobb Deep, Jay did what he does, which is to drive rivals to barking madness by ignoring them and then extinguish their careers by continuing to ignore them in feats of high-status hip-hop wu wei.

So, although art should not be competitive (although, in reality, it clearly, totally is), the easy winner here would be Trick Daddy (just kidding). May we all find 99 new problems more exciting and worthy of our grit than our current ones.

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