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Eminem: 50 Greatest Songs

The best from the bloody, bombastic, brilliant career of the hip-hop troublemaker

Though he’s been a multiplatinum, Grammy-winning star for almost 20 years, Eminem is not an unequivocally triumphant figure, either within pop music or within his own mind. Just listen to the vulnerability and self-doubt on his recent single “Walk on Water.” At age 45, the Detroit rapper continues to make art about how people are driven crazy by weakness and lack. It’s just now he’s finding it harder to joke about the darkness that has always fueled his best work.

Some fans celebrate only the funny “Slim Shady,” when the musical comedy is quality controlled by executive producer Dr. Dre. They eschew the more viciously somber, rock-leaning character studies helmed by Em and his longtime Detroit collaborators Jeff and Mark Bass. But spend serious time with Eminem’s entire catalogue and you quickly realize that those two sides of his music are inextricable, one always informing the other. 

When Eminem raps about violent, tragicomic death, he is furthering a grand murder-ballad tradition in folk and blues music. He’s also, on occasion, regurgitating grotesque sexist, homophobic stereotypes. But for a poor, white, emotionally unstable MC to excel in hip-hop and not be viewed as a villainous buffoon, he must possess prodigious artistic gifts and a real commitment to personal transparency. On these 50 essential songs, Eminem fearlessly displays that devotion to task and proves why he’s been one of pop music’s most fascinating, complex characters. 

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“Stan” (2000)

In 2003, Nobel Prize winner Seamus Heaney was asked whether he though any current musicians had inspired a renewed interest in poetry. “[Eminem] has sent a voltage around his generation,” the Irish poet answered. “He has done this not just through his subversive attitude but also his verbal energy.” Heaney didn’t cite specific lyrics, but the song most deserving of such high-flown praise is this epic diary of obsession. Playing off what functions as an ironic sample (by producer DJ Mark the 45 King) of Dido’s “Thank You,” an ode to simple gestures of kindness, Eminem unreliably narrates the story of “Stan,” an increasingly disturbed fan who religiously follows, then feels abandoned by, Em’s unhinged alter ego “Slim Shady.” Eminem, as himself, finally shows up to reply, but it’s too late. The song’s brilliance lies in its panopticon of personas and points of view, which shift from compassionate to cruel to bewildered. When interviewed, Eminem tended to characterize “Stan” as a conventional cautionary tale, but he wasn’t very convincing. “It’s kind of like a message to the fans to let them know that everything I say is not meant to be taken literally,” he told MTV at the time. “Just most of the things that I say.”

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“The Real Slim Shady” (2000)

After listening to an early iteration of The Marshall Mathers LP, Interscope boss Jimmy Iovine delivered some grim news: The record lacked a lead single. “I thought that the album was spectacular, but I thought they hadn’t taken it as far as they could,” Iovine remembered in a VH1 special. “They needed a song to introduce the album.” Dr. Dre agreed: “I knew we had a second or third single,” he acknowledged, “but we needed that big opener.” The pressure frustrated Eminem. “I can’t give you another ‘My Name Is,'” the rapper lamented. “I can’t just sit in there and make that magic happen.”

He didn’t come up with another “My Name Is”; instead, he topped it with “The Real Slim Shady,” which became Eminem’s biggest hit to date, reaching Number Four on the Hot 100. Though Eminem would soon transition into making somber world-beaters like “Lose Yourself” and “Cleanin’ Out My Closet,” “Real Slim Shady” is uproarious, with a carnivalesque synth line and a lyrical nod to a novelty track from Canadian comedian Tom Green. The rapper takes shots at everyone – pop stars, music critics, Will Smith, himself – but those freewheeling insults mask a unifying purpose: “I guess there’s a Slim Shady in all of us,” Eminem concludes. “Fuck it, let’s all stand up.”

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