Throughout the course of hip-hop history, no artist has epitomized the tragic characteristics of the gunslinger figure better than Eminem.

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The Wild West has always kept America in its thrall. So much so that over time, we transformed real-life outlaws such as Jesse James, “Doc” Holliday and “Wild Bill” Hickok into fictionalized anti-heroes—from Jack Schaefer’s Shane to Sergio Leone’s The Man With No Name Trilogy, to contemporary characters like John Wick. The gunslinger, as this trope is best described, remains one of the most prolific and complicated figures in modern storytelling.

In popular culture, the gunslinger is cool and rebellious—and challenges the institutions that be. Figures like John Wayne and Clint Eastwood remain iconic for playing these characters: lone wolves remembered for their saviorism—even if self-appointed—of the people and places being overrun by evil. The gunslinger, both in history and fiction, is often positively framed with all of these qualities in mind, and their audaciousness is treated as a merit badge. It’s a figure wrapped in tragedy, however, as the mythos of the gunslinger withers away as those who held such antiheroes in high regard realize the finiteness of their legacies.

Throughout the course of hip-hop history, no artist has epitomized the tragic characteristics of the gunslinger figure better than Eminem. As all iconic outlaws and antiheroes of pop culture often were and are, Eminem’s career is a study in both the importance of how one becomes a legend as well as their limits. That polarity is the foundation for his grandest achievements and his hardest falls and can be found most prominently in his earliest days as an artist.

Three years removed from his independently released 1996 debut, Infinite, frustration over poor sales and stalled buzz had begun to set in. Infinite was an admirable but conceptually milquetoast album filled with technically intricate and colorful lyricism, yet devoid of an engaging personality.

Marshall Mathers is a born lyricist, hellbent on maneuvering his way through rhyme patterns and metaphors with a sailor’s knot of tongue-twisting lyrics with clear influences, ranging from Ice-T to Big L to Masta Ace. Infinite, though, fell flat as a commercial jumping-off point. Eminem could out-rap anyone else in the room, but that didn’t mean people were going to listen.

It wasn’t until the 1997 release of the Slim Shady EP that the industry—and more specifically Jimmy Iovine, Dr. Dre, and Interscope Records—took notice of a stark alteration in Eminem’s rhyme style. The Slim Shady EP was more brazen and relentless. It traded in looser concepts and nonstop lyricism for darker, introspective tracks ranging from horrorcore rap to pop culture satire with a much tighter conceptual grasp.

As Interscope began to prioritize their future golden goose—and as tracks like “Just Don’t Give A Fuck” and “Just The Two of Us” (eventually retitled “97 Bonnie & Clyde”) transformed into foundational pieces of a potential full-length project—the Slim Shady persona mutated from Eminem’s frustrated circumstances and rebellious nature.

Enter Eminem’s 1999 major label debut album, Slim Shady LP, which arrived as one of the most audacious and monstrous records of the entire decade—both critically and commercially. However grandiose and unique Eminem’s entrance into hip-hop’s mainstream was, though, it became the first and subsequently most important step toward him becoming an iconic, and ultimately tragic, gunslinger figure in hip-hop.

The success of both Eminem’s Slim Shady persona, and subsequently the Slim Shady LP, follows the same traits of the gunslinger trope in American culture. Eminem’s alter ego, as he saw it, was neither the hero or villain, but the satirical and bitter antihero channeling everything from his difficult childhood to his frustration with the music industry into one rebellious figure.

The polarizing nature of Slim Shady is what made Slim Shady LP iconic for its time. He was an anti-hero daring enough to poke fun at the music industry—all while garnering fame by pushing the boundaries of storytelling and shock rap. Eminem could be Jesse James and John Wayne at once: an artistic outlaw refusing to conform, and a self-appointed savior of pop culture.

The success of Slim Shady LP rests almost entirely on how the framing of Eminem’s own narrative—and the gunslinger mentality that drove every ounce of the album—has played out over the past 20 years. It’s also evident that Eminem knew and understood his role in hip-hop and the responsibility of having such a role.

Twenty years on, the moments on SSLP that have aged the best are those in which Eminem juxtaposes his vigilante approach to pop culture with a self-aware reflection on his own role in that particular machine, resulting in the album’s most harmonic satire.

On “Role Model,” wonky guitar strings and flat drums guide Eminem down a high-flying trail of references ranging from former NFL running back Marcus Allen to cartoon character Foghorn Leghorn, all while Eminem himself critiques the ridiculousness of the song’s catchy violence. “Now follow me and do exactly what you see / Now you wanna grow up and be just like me?!” bookends every bar in the chorus, the facetiousness of it all remains as affecting as ever.

The album’s other high water marks, “Just Don’t Give A Fuck,” “If I Had,” and “Still Don’t Give a Fuck,” are cooked with many of the same ingredients as “Role Model.” Within those peaks, SSLP feels like a dazzling shootout of lyricism. On “Just Don’t Give a Fuck,” the first true watershed moment of Eminem’s career, the velocity with which the Slim Shady persona flips from remorseless psychopath to stand-up comedian still connects today based solely on his energy and execution alone.

The album’s darkest and most confrontational tracks, like “If I Had” and “Still Don’t Give a Fuck,” ground the chaotic nature of Slim Shady with the very isolated and lonely existence of the man behind the zany alter-ego.

For an album that has historically been labeled a “classic,” the Slim Shady LP isn’t without its warts. “Guilty Conscience,” for all of the controversy surrounding its subject matter, is burdened with dry and unchallenging production—and a concept that inspired substandard lyricism from both Eminem and guest Dr. Dre.

The same can be said for “My Fault,” which, despite its desire to be a boy band-esque mockery of pop music bullshit, falls flat once the novelty of its purpose wears off post-listen. Yet, neither track encapsulates the album’s most glaring weakness.

As the scope of Eminem’s career has widened over the past two decades, the album’s emptiest tracks, such as “Cum On Everybody,” “I’m Shady,” and “Brain Damage,” have become even more vacant.

Whether in brashness or ingenuity, many of the album’s achievements have either soured or turned to ash as it became apparent that Slim Shady was less Eminem’s alter ego and, instead, a faulty blueprint that he was using to position himself within hip-hop. In molding himself into the renegade gunslinger, raging against every single entity in his way, Eminem inadvertently failed to consider the long-term impact of such an artistic style.

Going back to the Western trope: the gunslinger narrative isn’t a tale of heroism as much as it is a tragedy about the eventual uselessness of such a figure the more that society outgrows it. The outlaws of the Wild West were privy to two fates: either die legends or live just long enough to see themselves diminished from a society progressing without them.

One year later, Eminem released his magnum opus and most exhilarating album, Marshall Mathers LP, which was then followed two years later by arguably the most mature and well-rounded project in his catalog, The Eminem Show. Still, the imprint Slim Shady LP made on the entirety of his career remains the most profound.

There are seeds planted within every album Eminem has released over the past 20 years that capture the polarity that plagues SSLP. From Encore to Kamikaze, especially, Eminem has sounded trapped within the idea that lyricism matters more than purpose, shock more than thoughtfulness, and showmanship more than substance.

Now, in 2019, Eminem’s career feels eerily similar to that of William Munny’s: the protagonist in Clint Eastwood’s Unforgiven, the story about an aging gunslinger living in regret about the life he lived but without a path out. The difference being that, in Unforgiven, Munny’s iconic character is aware of the fruitlessness of his life, and that its sum will forever be wrapped up in the mythology of his actions.

For Eminem, that self-awareness isn’t there. While SSLP will forever remain a success—characterized by its author’s fearless approach and 18 million copies sold worldwide—its creation ultimately led to Eminem becoming hip-hop’s aging gunslinger, continuously riding into a town that no longer fears or needs him, trying to survive off a legend instead of a life.