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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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“If I Had” (1999)

Eminem is known for his mania, his scorched-earth delivery, and for packing syllables into stuffed lines, but he is charmingly even-keeled on “If I Had.” That stems from the empty space in the production by the Bass Brothers, who helmed most of The Slim Shady LP. Their spare backdrops put a spotlight on Eminem’s tongue-twisting heroics. The rapper articulates a clear class consciousness, though of a type more often found in country music: “I’m tired of bein’ white trash, broke and always poor/Tired of takin’ pop bottles back to the party store/I’m tired of not havin’ a phone/Tired of not havin’ a home to have one in if I did have one on.” But don’t think he’s leading up to some final grandiloquent statement: “If I had one wish,” Eminem concludes, “I would ask for a big enough ass for the whole world to kiss.”

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“Rap God” (2013)

Rap God” is a mind-boggling, seething testament to Eminem’s own legacy, the rapper executing one acrobatic lyrical trick after another to demonstrate, chronicle and critique his hip-hop lineage. However he seems to shrug whenever he talks about the song, which was recorded in one take. He says he barely remembers that session; for him, it was just another day of mapping out multiple internal-rhyme schemes. In the third verse of this six-minute exhibitionistic display, he famously references J.J. Fad’s “Supersonic,” rapping at a stunning, Twista-level of speed and agility. “Everybody, every time, when they make a song, wants to say: I’m still here. Don’t forget about me,” Em said to MTV News. Though his pop-culture references have occasionally dated him in the latter part of his career, “Rap God” acknowledges the past with a thrilling freshness. 

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“Brain Damage” (1999)

In “Brain Damage,” Eminem tells the tale of DeAngelo Bailey, a bully who terrorized him in junior high. And in April 1999, a few weeks after The Slim Shady LP hit the charts, the real DeAngelo Bailey stood up and granted an interview to Rolling Stone to confirm that the grisly, over-the-top song, where a young Marshall’s brain falls out of his skull, was at least somewhat based on factual events. “There was a bunch of us that used to mess with him. You know, bully-type things … We flipped him right on his head at recess,” Bailey recalled. But in 2001, after Eminem’s star had risen higher and his mother Debbie Mathers was awarded a small settlement over his lyrics, Bailey had a change of heart and sued the rapper, unsuccessfully, for $1 million. 

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“Wake Up Show Freestyle” (1997)

In 1997, a then-unknown Eminem flew to Los Angeles from Detroit to participate in the battle-rap competition Rap Olympics. With the event sparsely attended, DJs Sway and King Tech, hosts of the hugely influential Wake Up Show, agreed to put the rapper and other competitors on-air to help increase their exposure. Eminem’s two verses blended Big L-inspired multisyllabic mastery (“But I’m more toward droppin’ an acapella/To chop a fella into mozzarella worse than a helicopter propeller”) with blistering humor (The duo’s favorite line: “Doctor Kevorkian has arrived/To perform an autopsy on you while you scream, “I’m still alive!”)

“His verse stood out because it was hardcore, funny and skillful at the same time,” Sway and King Tech tell Rolling Stone via email. “Humor at that level was really new. People were more impressed with lyrical/metaphor masters at that time. He had that and was adding a weird humor to it, so he definitely stood out. The feedback for weeks was all positive. … We just remember driving home and saying, ‘That kid had mad skills, man. It was unusual but dope.”

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“Criminal” (2000)

“‘Criminal’ was my new ‘Still Don’t Give a Fuck’ for The Marshall Mathers LP,” Eminem wrote in the 2000 book Angry Blonde. “That’s why it’s the last song on the record. It sums up the whole album.” Perhaps by design, “Criminal” comments on the controversy whipped up by Em’s debut, while at the same time ensuring that the follow-up album will generate even more outraged headlines. The first verse’s “Hate fags? The answer’s yes” was treated like a smoking gun in op-eds about Em’s homophobia, but that line, just like “Relax, guy, I like gay men” a few bars later, feels more like a shock-value punchline than a sincere declaration. Politically, “Criminal” is irresponsibly scattershot, but as a thesis statement for Eminem’s refusal of responsibility in the name of artistic license, it’s terribly on point. 

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“Any Man” (1999)

“So, I walk into D&D [Studios] and Eminem is sittin’ in the lounge – doesn’t look like a rapper, regular guy,” remembered producer Mr. Walt of Da Beatminerz (Black Moon, Black Star) in an interview with Hiphopdx. “I play beats for [Eminem] and he picks the beat for ‘Any Man.’ I never heard this guy rhyme [before]… So, he gets in the vocal booth and the first thing he says [in a high-pitched nasally tone] is ‘Hi!’ I look at my engineer like, ‘Oh my God, what did I just get myself into?'” Eminem goes on to unleash a series of wildly lewd and rude verses, as if he’s hoping to break as many taboos as possible in less than four minutes of classic New York boom bap. “I hope God forgives me for my sins,” he raps. “It probably all depends on if I keep on killin’ my girlfriends.” The session left Mr. Walt in a daze: “I looked at my engineer,” he said, “I was like, ‘Yo, what just happened?'”

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“’97 Bonnie & Clyde” (1999)

If Eminem is the flawed hero of his own music, Kim, his ex-wife and mother of his daughter, Hailie, is habitually his Achilles’ heel. On “’97 Bonnie and Clyde,” one of the earliest and most explicitly chilling takedowns of his femme fatale, he plays loose with Bill Withers’ “Just the Two of Us,” fantasizing about dumping Kim’s dead body into the ocean … with his daughter in tow. Hailie even appears on the track. “I lied to Kim and told her I was taking Hailie to Chuck E. Cheese that day,” Em told Rolling Stone for a 1999 cover story. “But I took her to the studio. When she found out I used our daughter to write a song about killing her, she fucking blew.” Eminem knew the consequences that such a track could have for his daughter. “When she gets old enough, I’m going to explain it to her. I’ll let her know that mommy and daddy weren’t getting along at the time.” Years later, the rapper was more contemplative. “Shit, hindsight is 20/20,” he told RS in 2013. “At that time, that was how I dealt with things. I didn’t really think about … what was right or wrong or whatever.”

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Jay-Z feat. Eminem, “Renegade” (2001)

Though it appeared on Jay-Z’s pinnacle achievement – 2001’s The Blueprint – the lyrically astounding “Renegade” was always Eminem’s song. He produced it and recorded the original version with Royce Da 5’9″ as the duo Bad Meets Evil. So, when Nas savaged Jay on 2001 diss epic “Ether,” charging that “Eminem murdered you on your own shit,” it was a distortion in more ways than one. In fact, Jay’s verse sketches lucid, entrancing metaphors that work both as introspection and inspiration. Plus, unlike every other major MC who appeared on a track with Eminem, he doesn’t strain to battle on Em’s gloriously spiteful turf. He follows his own artistic path. Good decision since Em’s tightly packed internal rhymes burst with assonance and he flows almost casually yet no less emphatically – that old familiar ire only pitching up his voice toward the end of his last verse so it feels more earned. On 2009’s “A Star Is Born,” Jay-Z gave his official blessing: “His flow on ‘Renegade,’ fucking awesome, applaud him.”

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“Role Model” (1999)

More than any other major artist, Eminem has consistently toyed with and questioned the public’s desire to turn famous artists into paragons of virtue and wisdom. Here, he fires off absurd insults, injures himself and envisions scenarios where he’s embodying Norman Bates (“Mother, are you there? I love you”) or beating up Foghorn Leghorn “with an acorn,” hilariously satirizing the very idea that younger fans would ever mimic him. “To me it’s just a rap record. The message behind it was just complete sarcasm,” Eminem wrote in Angry Blonde. “I wanted to be clear: Don’t look at me like I’m a fucking role model.”

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“White America” (2002)

By 2002’s The Eminem Show, the rapper had faced off against two consecutive vice-presidential wives (Tipper Gore and Lynne Cheney), in their crusades to censor rap. He strikes back in the album’s opening track, where he demands to know how he became one of America’s Most Wanted. In print, his interrogation of his position as a rich and famous white rapper seems almost matter-of-fact. (“It’s obvious to me that I sold double the records because I’m white,” he said to Rolling Stone.) But in “White America,” set to Em’s own arena rock-sized production – thudding percussion and the sound of fighter jets – those same sentiments feel like he’s declaring a state of emergency. “See, the problem is,” he raps urgently, casting himself as a generational figure, “I speak to suburban kids/Who otherwise woulda never knew these words exist/Whose moms probably woulda never gave two squirts of piss/’Til I created so much motherfuckin’ turbulence.” 

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“Marshall Mathers” (2000)

The song carrying Eminem’s birth name reveals the man behind all the personas as he struggles with paranoia and disgust for everyone who is now monitoring his every post-fame move. He petulantly jabs at bubblegum pop, boy bands and fellow Detroit pottymouths the Insane Clown Posse. “I felt that what I needed to talk about in the verses was just me and my opinions,” wrote Eminem in Angry Blonde. “So I touched on everything from the newest trends in hip hop (which I’m not really with), to ICP, to my mother, to my family members who don’t know me and always wanna come around. I wanted to just spit fire in each verse and have the soft-ass innocent chorus.” He did, in what came to be the mid-period Eminem style, entrancing millions with his passion and skill, while likely alienating others with his casual slurs.

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“‘Till I Collapse” feat. Nate Dogg (2002)

Recorded circa “Lose Yourself,” this standout from The Eminem Show was built around the beat from Queen’s “We Will Rock You” and is, in many ways, a lyrical companion piece to 8 Mile‘s tale of trial and toil. “You gotta search within you/And gotta find that inner strength/And just pull that shit out of you,” Em intones at the song’s outset. But it is Eminem’s ranking of the best all-time rappers, which comes halfway through the song, that made all the headlines. “I got a list … /It goes Reggie [a.k.a. Redman], Jay-Z, 2Pac and Biggie/Andre from Outkast, Jada, Kurupt, Nas and then me.” Chatter among pundits ensued, but Eminem was transparent about his respect for the genre’s greats. “Being a student of hip-hop, in general, you take technical aspects from [different] places,” he told Rolling Stone in 2013. “You may take a rhyme pattern or flow from Big Daddy Kane or Kool G Rap. But then you go to Tupac and he made songs. His fucking songs felt like something – “Holy shit! I want to fucking punch someone in the face when I put this CD in.” Biggie told stories. I wanted to do all that shit. My goal … is to be technically able to satisfy every underground or every great rapper there is and also be able to try to incorporate it into a song. And make the song feel like something.”

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“Guilty Conscience” feat. Dr. Dre (1999)

“I remember Animal House when the girl passes out and the guy was about to rape her. He had a devil on one shoulder and the angel on the other saying don’t do it,” said Eminem, defending this song to the Los Angeles Times in 2010. “So, we did the same thing, only [with] a little more graphic detail.” On one of the most compelling tracks from The Slim Shady LP, Eminem introduces three different characters in three increasingly toxic scenarios with Emimen and Dr. Dre playing the characters’ good and bad consciences arguing with each other. The album version sounds like three creepy skits stitched together by voice-over, but the single version stacks three distinct eras of teenage desire: The chorus is inspired by the chaste yet spiritual “I Will Follow Him” by Sixties teenybopper Little Peggy March; Dre’s beat jauntily interpolates Ronald Stein’s “Pigs Go Home” from the Vietnam-era youth movie Getting Straight; while Dre and Em’s lyrical interplay speaks to the increasingly jaded and cynical MTV generation. References to Son Doobie of Funkdoobiest’s widely mocked foray into porn, the 1995 movie Kids and Dre’s own history of assault complete a deft satire of violent male impulses.

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“Kim” (1999)

Though 8 Mile‘s “Lose Yourself” became Eminem’s Academy-Award-winning song, his most filmic performance was on this six-minute-plus dramatization of his own horrendously dysfunctional marriage to supposed true-love Kim Scott Mathers. His jealous, grindingly detailed rage surges and recedes in an abusive call and response, never losing intensity, as the Bass Brothers’ rock-centric track storms on. It climaxes at the end of the second verse, where he screams “Get the fuck away from me! Don’t touch me!/I hate you! I hate you! I swear to God, I hate you!” Then recoils, in tears: “Oh my God, I love you!” The “Kim” character (also played by Em) apologizes, but she’s blotted out by her husband’s howling cry. It’s as if John Cassavetes’ A Woman Under the Influence was reshot with Peter Falk’s husband in the spotlight instead of Gena Rowlands’ wife, replaying his climactic line, “I’ll kill ya, and I’ll kill these sons-o’-bitchin’ kids,” throughout a Tarantino-esque blood-spurting third act. Though overshadowed by its graphic depiction of violence against a woman, Eminem’s performance is powerful and intense. The real-life Kim reached a settlement after suing her husband for $10 million.

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“Cleanin’ Out My Closet” (2002)

An innately combative MC, Eminem dreamed up his alter ego Slim Shady so he could unload on the world with impunity – morality police, music critics, other white rappers. But his true-north antagonists have always been wife Kim and mom Debbie. And of all the songs about his mother – both absurd and apologetic – “Cleanin’ Out My Closet” is the most deeply affecting, even becoming a Top Ten pop hit. DJ Head’s syncopated, almost delicate drum loop darts around the dark, spare instrumentation (bass, guitar, keyboards played by co-producer Jeff Bass), while Eminem excavates a lifetime of debilitating parental emotions. The song’s tone nimbly fluctuates, especially with the haunting “I’m sorry, mama,” chorus. Finally, there’s the climactic betrayal – when his mom, according to Em, tells him that she wishes he’d died instead of his uncle/best friend Ronnie (who committed suicide in 1991). Eminem barks his chilling reply into the void, “Well, guess what? I am dead – dead to you as can be!” In 2014, fellow Detroit native Angel Haze was inspired by to revive and revise “Cleaning Out My Closet” to tell her own tale, one of being sexually abused as a child. “I was so angry,” she told The Telegraph. “It was like catharsis to listen to [Eminem].”

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“Get You Mad” (1999)

For this loony appearance on This or That, the Interscope-backed mixtape from influential Bay Area radio hosts Sway and King Tech, Eminem lays down a proper studio recording of some reference-packed bars initially spit for their Wake Up Show. Like the hip-hop version of his eventual pop-star takedowns, Em pokes fun at the latest round of rap dramas, takes down the current crop of platinum MCs, adds kindling to some of his earliest intra-industry feuds, throws out some tasteless jokes and lacerates the record business (“Don’t act like a fan, you wanna get signed/Get the whitest A&R you can find, pull him aside and rap as wack as you can”). “All we did was reach out to people that we knew were dope, and were gonna last,” producer King Tech told HipHopDX about making their 1999 compilation, which also featured early performances from Tech N9ne and Crooked I. “I’m from an era where if the beat is bangin’, just let him roll. Let him do what he does. I remember him callin’ me, ‘Tech, you think I gotta change the hook? I might’ve been too crazy.’ I was like, ‘Kid, I love that shit!'”

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“Bitch Please II” feat. Dr. Dre, Snoop Dogg, Nate Dogg, Xzibit (2000)

Beyond some of the greatest collaborators of Dr. Dre’s solo peaks perfectly complementing each other, “Bitch Please II” captures the brash undercard confidence that makes Em’s unapologetic attitude so bracing. That take-me-or-leave-me armor works, in large part, because he constantly accents his cynicism with humor: his Snoop Dogg-tweaking opening lines and off-key Nate Dogg harmonizing envelope a stolidly serious Dre production in Em’s waggish glee. At his core, Eminem wants you to see that he’s just joking — “somewhere deep down there’s a decent human being in me” — without sacrificing any of his music’s outrageously rebellious spark and impact.   

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“The Way I Am” (2000)

“If you think I’m an asshole, then I’m gonna show you an asshole,” he told SPIN of his motivation behind the angst-ridden 2000 single that adapts lines from Eric B. & Rakim’s “As the Rhyme Goes On.” “If you call me a misogynist, I’m a misogynist. If you say I hate gay people, then I hate gay people.”In the wake of releasing The Slim Shady LP, Eminem became one of hip-hop’s most polarizing figures: PTA meetings were dedicated to his violent lyrics; conservative organizations decried him as poisonous to young people. This was hardly a shock to the rapper. “Look, I know what people say and how they feel about some of the language I use, topics I rap about and stuff I present,” he told Rolling Stone in 2013. And so on “The Way I Am,” the self-flagellating second single off The Marshall Mathers LP, Eminem beats his critics to the punch. He embraces the role of a villain, happy to aggressively play it up.