Eminem: 50 Greatest Songs

Contrary to his well-earned reputation as a fearless cultural provocateur, Eminem has long written sentimental songs that give context and nuance to his emotional outbursts. “Headlights” from The Marshall Mathers LP2 may be the most necessary addition to this less-celebrated aspect of his canon because he finally tries to make amends with his mother – whom he had mocked mercilessly on 1999’s “My Name Is,” then excoriated, in heartbreaking fashion, on 2002’s “Cleanin’ Out My Closet.” Em’s use of Debbie Mathers as a musical antagonist frayed their relationship and resulted in a lawsuit, but on “Headlights” he apologizes for his part in their estrangement. “I went in head first/Never thinking about who what I said hurt/And what verse/My ma probably got it the worst,” he raps. He doesn’t downplay their brutal conflicts, like how she kicked him out on Christmas Eve when he was a teenager, and how they’ve barely spoken since his career took off. But he resists indulging in the kind of blind rage that he’s unleashed in the past. “I hope you get this message that I will always love you from afar,” he concludes. When asked about “Headlights” during a SiriusXM Town Hall session, Eminem responded, “What I said on the record is what I have to say about that. … There’s no need for me to elaborate on it.”

This deranged dark comedy about how dangerous love can be isn’t what most fans expected from two of hip-hop’s most skilled lyricists. You can thank Rick Rubin, who sent Eminem the cheery, oldie-but-goodie loop (built on Wayne Fontana and the Mindbenders’ 1965 smash “A Groovy Kind of Love”) because he couldn’t hear anyone else over it. (“I don’t know if I want to hear Jay-Z on that record,” he said to Complex.) But it was Em’s idea to feature Kendrick Lamar, whom he’d recently met, to Rubin’s surprise. Even Em got more than he bargained for out of the collaboration. When the two MCs met at the studio, Eminem kicked out Lamar’s crew, as if to see whether his guest indeed wrote his own lyrics. Not only did Em get a hook and an outrageous Slim Shady-esque verse from Lamar, but he also had a song that forced listeners to reckon with the conceptual genius of both rappers.

In 2013, Jay-Z and Eminem became the first examples of what happens when the most famous rappers in the world are over 40. While the former embraced his maturity by collecting modern art and basketball arenas, Eminem brilliantly cut a figure as a confused hermit over the churning Joe Walsh riffs of “So Far.” Here, he raps about a fan noticing his crow’s feet, his inability to understand downloads and Facebook, and still feeling bad when pretty girls catch him picking his nose. Or, as he says to Zane Lowe, “I’m complaining about shit that I have no business really complaining about.”

The blockbuster collaboration between Eminem and Rihanna grew out of a loop that the British producer Alex Da Kid brought to songwriter Skylar Grey, which inspired her to write about her mistreatment by the music industry. When Eminem got the track, he wanted it for his Recovery album, but felt that only Rihanna could bring the necessary emotion. The song’s central metaphor shifted with Rihanna’s participation and became more explicitly about the violence that can erupt between two romantic partners – Eminem drew on his experiences with his ex-wife and lyrical foil Kim, while Rihanna’s memories of the violence at the hands of then-boyfriend Chris Brown tinged her unforgettable wails on the song’s chorus. “It’s something that we’ve both experienced on different sides of the table,” Rihanna told Access Hollywood in 2010. “[Eminem] pretty much just broke down the cycle of domestic violence, and it’s something that people don’t have a lot of insight on.”

On “Roman’s Revenge,” the throwdown between two of the 21st century’s most technically proficient crossover MCs, Eminem and the then-ascendant Nicki Minaj trade barbs (and au courant references to iPods and Giants quarterback Eli Manning, as well as a shout-out to Busta Rhymes’ verse on A Tribe Called Quest’s “Scenario”) over a malfunctioning-Nintendo beat crafted by Swizz Beatz. “Absolutely the most fun song on Pink Friday ­– it gave me life, dahling,” Minaj said, in her Roman Zolanski persona, during a 2010 MTV interview. After clarifying that she collaborated with “Slim Shady” not Eminem, Minaj was asked who offered up the “crazier” character. She broke up laughing and exclaimed, “It has got to be Slim!”

For some, Royce the 5’9″ was still the best MC in Detroit in August of 1998, when he and Eminem paid a rite-of-passage studio visit to Stretch Armstrong and Bobbito Garcia’s influential New York underground radio show. Em and Royce flung freestyle spittle for 12 relentless minutes, stoked by what bystander Noah Callahan-Bever called “a pharmacopeia of drugs.” Just more than a year after that dazzling display and the transformative impact of The Slim Shady LP (which featured Royce on the track “Bad Meets Evil”), the duo released an indie 12-inch. The B-side, “Scary Movies,” was the keeper, a peak indie-’99 banger, with a strings-swept, RZA-gritty thump and some of Em’s most ferocious rhymes – “Any man plannin’ to battle’ll get snatched outta his clothes so fast it’ll look like an invisible man standin’.” But playing sidekick to Em didn’t suit Royce and their paths eventually diverged until an eventual rapprochement (and reunion album) after the 2006 death of their mutual friend, D12’s Proof.

The de facto sequel to Eminem’s 1998 smash “My Name Is” and 2000’s “The Real Slim Shady” is a manic, quicksilver whirl through Eminem’s shit list, launching acid-laced broadsides and flipping the middle finger at real and imagined enemies, including then-Vice President Dick Cheney (whose wife Lynne took Em to task during a 2001 war of words with Madonna); DJ/producer Moby (who was “running his fucking mouth” at the Grammys, according to the rapper in a 2002 Rolling Stone interview); the Federal Communications Commission (which levied, and then rescinded, a fine against a Colorado radio station for playing the clean version of “The Real Slim Shady”); and his mom (who had taken him to court over his talk on “My Name Is”). “It’s, like, I need drama in my life to inspire me a lot, instead of just trying to reach for something,” Eminem told The Face in 2002.

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.”

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.

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.

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.”

“‘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.

“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?’”

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.”

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.”

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.”

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.”

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.

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.”

“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.

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.

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].”

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!’”

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.

“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.

In the summer of 1998, when Aftermath/Interscope mailed out 12-inch promos of “Just Don’t Give a Fuck” as the first single from Eminem’s major-label debut, he was still a battle-rap rumor. This rowdy-rebel boast was the wider world’s first brush with the wiseass white MC, who instantly tweaks our perceptions, tagging himself “Slim Shady,” his sociopathic alter ego, in the first line. Soon after, there’s a goofier intro – “My name is Marshall Mathers, I’m an alcoholic” – which spikes the mix with a third persona via his government name. This is the foundational head trip: Who is this person? Are all of these narrators unreliable? Though not the pop wallop of follow-up “My Name Is,” “Just Don’t Give a Fuck” was its own defining shot – more polished, scintillating and frisky than the version on 1997’s Slim Shady EP (credit to executive producer Dr. Dre). It wildly sprays the sky, with the three-headed rapper waving “two Glocks, screamin’ ‘Fuck the world’ like 2Pac.”

Even at the peak of his powers, it was a bold move for Eminem to get on a track with a posthumous Notorious B.I.G. verse. The antisocial jolt of Biggie’s lines on the thunderous “Dead Wrong,” produced by Bad Boy Hitmen Chucky Thompson and Mario Winans with Diddy hovering nearby, were among his most potently scathing. Yet Eminem practically matches him, sketching an antihero heel turn that scoffs at norms and good taste. Rather than reaching for Big’s legendarily blunt, declarative phrasing, Em eases into his verse easily, abstractly, as if he were writing a Wikipedia page on theistic Satanism: “There’s several different levels to devil worshipping. …” But it’s a false sense of banality as the verse winds its way into a maze of malevolence and brutality.

In late 1999, Eminem called his mentor Dr. Dre. He doesn’t remember what they were supposed to discuss, but he was struck by the jauntily frenetic jazz loop (possibly borrowed from Jacques Loussier’s 1979 composition “Pulsion,” as a lawsuit claimed) that Dre was tinkering with in the background and demanded to use it. Though Em already had a triple-platinum, Grammy-winning album and a Rolling Stone cover touting his “dirty white boy rap,” he was eager to warn folks that he was only getting started. (To quote Em’s Angry Blonde: “If anything … I got worse.”) To wit, “Kill You” uncorks a delirium of comic-book revenge, shading irony with savagery to bait and ridicule his critics. But the track is most fascinating impressive for its absurdly specific and self-aware depiction of an unhinged superstar (though, unfortunately, most of the ire is at the expense of women and features a homophobic slur). Vice presidential wife Lynne Cheney was among those taken aback. During a 2000 Senate hearing, she cited “Kill You” – in particular, Em’s perverse revenge scenario against his estranged mom, who had sued him for $10 million after lyrics about her appeared on The Slim Shady LP – as one reason the music industry needed a rating and labeling system to protect children from harmful subject matter.

Eminem’s 1998 breakout single burst from the earliest meeting between the then-unknown MC and the storied producer Dr. Dre, who had been fiddling with a sample from Labi Siffre’s 1975 soul strut “I Got The…” “I was, like, man, listen, I put this sample together – tell me if you like it. And I hit the drum machine, and maybe two or three seconds went by, and he went, ‘Hi! My name is … My name is …,” Dr. Dre recalled in the 2017 documentary The Defiant Ones. “Like, ‘Yo, stop. Shit’s hot.’ That’s what happened on our first day, in our first few minutes of being in the studio.” Eminem’s combination of nonstop pop-culture punch lines (he name-checked Nine Inch Nails, the Spice Girls, Pamela Anderson Lee and Kris Kross in the first verse), intricate rhyme schemes delivered in his Michigan drawl, cartoonishly violent imagery and a music video in which he gleefully parodied TV hucksters caused “My Name Is” to become a parental-advisory-emblazoned crossover sensation and MTV mainstay (albeit with heavy censoring). While it only peaked at Number 36 on the Billboard Hot 100, it won the Grammy for Best Rap Performance in 2000, establishing Eminem as one of hip-hop and pop’s brightest talents.

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.”

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.

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.”

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.”