Eminem’s fall from grace has been a tragic and shockingly rapid one. It was as recently as a half-decade ago that Slim was considered to be the most relevant artist in all pop music, selling millions, earning critical raves, even winning an Oscar or two. A mere year or two later, the man’s career was done and done–a truly spectacular flame-out that was only fortunate in that it didn’t (to my knowledge) involve any sex scandals or racist radio interviews. How did this all happen? Well, let’s examine the ten moments that transformed Eminem from seeming like the Bob Dylan of his generation to making a feud with Brett Michaels seem like something close to a fair fight.
I like Unterberger’s list, but I think he misses the actual things that undid Eminem. Well, to be more precise, he expertly tracks Em’s descent into embarrassingly insanity, but he doesn’t pinpoint the events that made Marshall Mathers irrelevant. I’d say (and I have a feeling this has been mentioned before, but I can’t for the life of me think where) the two events that properly triggered Em’s demise were his duet at the Grammys with Elton John, and the critical praise he received for his role in 8 Mile. The former neutered his ability to be controversial, and the latter placed his persona into a context that could be understood by those who didn’t usually pay attention to rap music and didn’t know how to read its narratives. Those of us who listen to rap understand that what a rapper says isn’t what a rapper does, and 8 Mile explained this: “Oh I get it, he’s acting.” And, so, once these two events conspired to prevent Eminem from being controversial and unreadable,1 he had to fall back on the less interesting parts of his act: the celebrity mocking and the songs about how much he loved his daughter.
It’s ironic that the things that did most to undo Mathers’ career were some of his biggest successes, and one of the biggest nails in his coffin was correspondingly one of his big successes. Let’s not forget that Em came along at a time when mainstream rap was money, cash, hoes, and Em’s grimy horrorcore was ideally situated to make him seem like he was a credible problem with society. But when Em put 50 on, gangsta rap came back in a big way — as did its cousin, trap rap — and we all remembered to be scared of black guys with guns again. How could a white actor really be public enemy number one when the charts were suddenly filled with louche charmers with a gun in one hand and a bag full of kis in the other?
And let’s not forget 9/11 and the Iraq war; all of America was scared of Osama Bin Laden, and half of it was scared of the President, and both of those things were more pressing and real than that guy who talked about stabbing gay people as a metaphor for his linguistic abilities. Slim Shady was a real Clinton-era villain, as Slim himself acknowledged: “You want me to fix up lyrics while the President gets his dick sucked?”
The end of the Clinton era claimed Eminem, and took with it those other two icons (Blink-182 and American Pie) of a curious time when hyperbolic gross-out humor seemed threatening, but the question is, how did the fourth horseman of the End of History apocalypse survive? As much as I’d claim it died a creative death around the same time Eminem did, “South Park” endures as a commercial success, even if it doesn’t quite have the cultural cache it did in the Clinton-era (remember the “Oh My God, You Killed Kenny” t-shirts?). How did Matt Stone and Trey Parker flourish while Eminem did not?
 Also, he was now too rich to credibly tell stories about being white trash from Detroit a la “If I Had.” Jay-Z encountered a similar problem a few years later, and temporarily solved it with American Gangster by embracing the film format. I guess 8 Mile lengthened Em’s career by acting as a similar cipher, but I wonder if he could return to that now, and make a concept album about being younger, more poor and miserable, and not a famous rapper?