1991: Et tu, A Tribe Called Quest?

Despite being loved as one of the smartest, most progressive, most generally awesome hip-hop groups of the '90s, even A Tribe Called Quest weren't immune to some bonehead plays. The most regrettable of these is the unreleased "Georgie Porgie," the original version of "Show Business." While "Show Business" is a cautionary tale about the music industry, "Georgie Porgie" features lines like "Getting done up the butt box / Oh my God, how gross can one be? / Well anyway, better him than me," and Q-Tip's nonchalant parting shot, "Call me homophobic but I know it and you know it / You're filthy and funny to the utmost exponent." Grand Puba remains unrepentant, calling his verse "probably one of the best verses I ever wrote." In fact, when the label wouldn't release the song, he refused to record a verse for "Show Business." 

1994: Notorious B.I.G. releases "Me and My Bitch"

...which features the line "You look so good, I suck on your daddy's dick," and weirdly, even being willing to make that claim jokingly seems almost progressive in the context of '90s rap. Not exactly a statement of solidarity, but hey, baby 

2000 - 2001: Eminem, confirmed homophobe, duets with Elton John, confirmed gay dude

Emerging in the late '90s, Eminem doubled-down on homophobia. Some of his greatest hits:

• "You faggots keep egging me on till I have you at knife point, then you beg me to stop?" ("Kill You")

• “My words are like a dagger with a jagged edge / And I’ll stab you in the head, whether you’re a fag or les / A homosex, hermaph, or a trans-a-ves / Pants or dress? Hate fags? The answer’s yes." ("Criminal")

• "New Kids on the Block sucked a lot of dick / Boy-girl groups make me sick / And I can't wait 'til I catch all you faggots in public, I'ma love it" ("Marshall Mathers")

And on it went... until he performed a duet with Elton John at the Grammys. They hugged afterwards, and homophobia was defeated forever. On SNL, Tina Fey memorably zinged Eminem over the incident, reporting, "When asked if he felt conflicted about working with the obviously gay performer, Elton John said, 'I don't have a problem with it.'"