Date: February 21, 2001
The Moment: Two albums in, and Eminem had simultaneously become an international pop star, a critical darling, and the target of every special interest group known to man (except for, maybe, the ACLU). Liberal, conservative, it didn't matter. Eminem could offend the conservative moral majority and GLAAD on the same song. Imagine the world's outright shock, then, when Em not only performed his somber fan-gone-bad anthem "Stan" with gay icon Elton John at the 2001 Grammys, but when Eminem and Elton John also embraced, held hands, and raised them together at the end of the performance.
The Impact: As GLAAD continued to object to Eminem's ostensibly homophobic lyrics via protest outside the Grammys, the performance was already being celebrated by fans and critics alike as one of the greatest pop culture water-cooler moments of the new decade. Two incredible artists—seemingly at odds with each other musically and socially—joined together. It set a high bar for bringing nuance into dialogues about what musicians should and shouldn't sing, do, or say: Elton John had crossed the gay cultural picket line for Eminem, and Eminem had shrugged off rap's (still) conservative ideas about gay men in America with ease.
The Upshot: In the end, both Eminem and Elton John saw more acclaim than fallout over the matter, upsetting whatever previous expectations of them should do. The moment brought a renewed interest in younger audiences for Elton John and older audiences for Eminem, who won an Academy Award (something, it could be pretty reasonably argued, that he would have never seen without his Elton John collaboration coming before it).
The friendship between Eminem and Elton John continued for the next decade: In 2010, it came out that Elton John had been helping Eminem kick his addiction to prescription drugs. In 2011, Elton John told Rolling Stone that Eminem gave him and his husband two "diamond cockrings" as a wedding present.