21. Role Model (1999)

With jokes about the alleged OJ murders and Lauryn Hills mythical hatred of white men, this is Eminem starting to realise his power as a cultural provocateur. The fact he bluntly erases his predecessor (I saw Vanilla Ice and ripped out his blonde dreads) also feels significant, with the Detroit native reshaping the idea of the ascendant white rapper.

20. Without Me (2002)

With a mischievous beat that sounds as if it was crafted by Dr Dre rhythmically squeezing a bunch of clowns noses, this is a continuation of the silly pop theatrics of The Real Slim Shady and My Name Is. When Eminem claimed rap would be empty without him around, it was hard to disagree.

19. Cleanin Out My Closet (2002)

A bit like watching a white trash family drama unravel on the Jerry Springer show, this intensely autobiographical song works because Eminem isnt afraid to operate from a place of weakness. Em also shares his mission statement as an artist, rapping: Give em hell for as long as Im breathing.

18. Scary Movies (1999)

Eminem has always made an artform out of killing people and his absurdist pledge to Throw you down a flight of stairs / Then Ill throw you back up them is undeniably hilarious. Scary Movies is a reminder of a time when Em wasnt just a great rapper, but a great comedian, too.

17. The Way I Am (2000)

As good as The Slim Shady LP was, it was a bit too heavy on dick jokes, and this highlight from its follow-up showcases clearer artistic growth. A haunting meditation on fame, its a paranoid, inward-looking tale of being so famous that you get followed to the bathroom.

16. Hellbound (2000)

Rapping over regal music from beat-em-up game Soulcalibur, Ems promise to fuck the planet until it spins on a broken axis projects a larger-than-life confidence. Eminem slashes through the beat like a katana sword, writing the hyper-animated blueprint that Kendrick Lamar and Nicki Minaj would later follow.

15. Jay-Z Renegade (feat Eminem) (2001)

Originally an Eminem collaboration with frenemy Royce Da 59, Ems potent critique of middle America proves he was one step ahead of his broadsheet critics. He is operating at the height of his powers, with verses so vivid that Nas even taunted Jay-Z with the barb: And Eminem murdered you on your own shit.

14. If I Had (1999)

Em has rarely sounded this dejected, with the artist wondering what he must sacrifice in order to make a million dollars. When he would rap about his personal life later on in his career there was too much syrupy sentimentality and self-pity, but here (where he recalls earning $5.55 an hour) Eminem has never sounded so relatable.

13. Superman (2002)

The kind of song that might get an artist cancelled today, Superman is a twisted take on the love bops Nelly and Ja Rule were routinely pumping out. Endlessly catchy, its the closest Em has come to a club banger, and his problematic Lothario dazzles rather than disgusts because he dares you to take him seriously.

12. Im Back (2000)

Not all of Dres beats on the Marshall Mathers LP have aged that well, but Im Back remains truly compelling theme music for a comic-book villain. Eminem fans the flames by threatening to murder Columbine bullies; at this point, he genuinely felt like pop cultures most provocative son.

11. Guilty Conscience (1999)

Playing into media claims that rap music was leading young people astray, rarely has a mainstream rap single been so conceptual, as Em and Dre play the two conflicting sides of the male conscience. Em tells Dre who assaulted TV host Dee Barnes in 1991 hes in no position to lecture someone else on how to treat a woman. Its still bold.

10. Deja Vu (2009)

This is a three-dimensional account of what its like to be a person with the kind of privilege that might fuel a drug addiction. Em recounts being in an ambulance after an overdose, but the fact he does so while joking about his fears of suffering a cliched death like Elvis makes for an endearing listen.

9. White America (2002)

Aware that he was every parents worst nightmare, Eminem dissects his cultural influence with real precision. Screaming his vocals from the very back of his throat, he also grapples with his white privilege, acknowledging: If I was black, I wouldve sold half. White America showed rappers they could be rock stars, too punk rappers such as Slowthai and Denzel Curry will have learned a lot from this.

8. Remember Me? (2000)

Designed to be blasted out of a car in a dingy alleyway at 1am, this abrasive shot of horrorcore is as raw as an exposed nerve ending. Each verse is more unhinged than the last, with Eminem fully embracing his growing mythology as raps angry blonde.

7. My Name Is (1999)

You couldnt make these kind of jokes today, but back in 1999, this subversive doozy really felt like Slim Shady was breaking through MTVs glass ceiling. Em played the role of pop cultures Dennis the Menace ever so well, mocking the misguided idea that rappers should be considered role models over a catchy Labi Siffre sample.

6. Square Dance (2002)

Eminem is too self-aware to create truly transcendent moments, but this experimental banger is the closest he ever got to crafting one. Tapping into post-9/11 paranoia, Em plays the role of the demented ringmaster, bringing you into his garish circus with aplomb. It is basically the rap version of Being For the Benefit of Mr Kite!

5. Lose Yourself (2002)

This is the Rocky theme song reimagined for millennials, with Eminem at his most inspirational while forcing you to empathise with the plight of the working class. Its rare that a whole generation knows the lyrics to a rap song, but Lose Yourself is more than worthy of that honour (even if Marty disagrees).

4. Kim (2000)

Arguably the darkest song to ever appear on a diamond-selling album, the murderous chaos of Kim powerfully reflects a misguided lovesick rage. Em switches between male and female voices with an unsettling schizophrenic power, with the bittersweet chorus also strangely enchanting. This broke new ground for storytelling rap, and made your mum lock away your copy of The Marshall Mathers LP in a safe, for ever.

3. Dr Dre Forgot About Dre (feat Eminem) (1999)

This track perfected the juxtaposition between Dr Dre as the world-weary OG and Eminem as his deranged apprentice. Rapping like a cartoon rottweiler, Em chomps his way through the beat in a way that is linguistically dizzying. As far as perfect producer and rapper dynamics go, this remains the one to beat.

2. The Real Slim Shady (2000)

If MTV had become a little safe and too draped in shiny suits by 2000, this was Eminem attempting to liberate it from its excesses and give pop cultures trashier icons (Will Smith, Fred Durst) a much-needed spanking. This was a single so big that it opened up hip-hop to the suburbs and made millions of white teenagers dye their hair blond.

1. Stan (2000)

Six-minute epics about crazy fans who drown their pregnant girlfriends dont usually top the pop charts, but Stans storytelling was so vivid and claustrophobic that it grabbed you by the neck and forced you to get into the back of that car. This shifted the pop paradigm completely and gave a face (and name) to the kind of toxic fan culture that would later multiply with the explosion of social media. As far as rap storytelling goes, it is unlikely Stan will ever be bettered. This is Eminems Stairway to Heaven, and the fact he could even make Dido sound bearable is testament to just how good he used to be.