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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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“Lose Yourself” (2002)

Eminem has always drawn a line between 8 Mile‘s protagonist, Rabbit, and his own life: The film’s central character was loosely based on his own come-up, but it was not strictly autobiographical. Still, it’s easy to hear much of the rapper’s own grind in the film’s lead single. In many ways, it’s the realism and overcoming-all-odds sentiment of “Lose Yourself” that propelled it to become the biggest hit of Eminem’s career and the first rap song to win the Academy Award for Best Original Song. Eminem and producer Jeff Bass had recorded a demo a few years earlier, but revisited it during the Detroit-based production of 8 Mile; Eminem wrote the song’s confessional lyrics only after receiving the film’s script. “I had to make the song while I was in the movie,” he told Funkmaster Flex. “Because once I stepped out of that movie I wouldn’t feel like I was in [the character.]” He cut the track in rapid-fire fashion. “”He came in and laid down all three verses in one take,” recalled engineer Steven King. “Jaws dropped – we were, like, ‘Oh, my God!’ This story had been building up in him.”

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Dr. Dre feat. Eminem, “Forgot About Dre” (2000)

Despite its origins as a hard-nosed diss track torching Suge Knight – written in secret and presented to Dr. Dre by Eminem – “Forgot About Dre” became the artist/producer/A&R visionary’s career capstone, winning a Grammy and achieving pop-culture ubiquity five years after his last Top 40 hit. “People were saying that I didn’t have it anymore and that I hadn’t made a good record in years,” Dr. Dre told Rolling Stone at the time. “I just can’t ignore that shit. … Now what do you people have to say?” The creeping-outside-your-window ambience he conjures – like a tightly plotted big-screen adaptation of the Dungeon Family’s vividly sprawling vignettes – possesses an almost stately, imminent threat. This song a rap fan wrote for a pioneer also might be Eminem’s crowning validation. The artful verse structure he creates for both himself and his mentor allows them to spit scorn or self-affirmation in perfectly calibrated declaratives or dazzling double-time. Plus, Em voices the unforgettable chorus in a battle-rap rat-a-tat that effortlessly ferries a dizzy melodic swoosh. 

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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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