2004: 50 Cent doesn't like the thoughts that are in gay people's heads

Between his various entrepreneurial endeavors in the fields of crack cocaine and Vitamin Water, 50 Cent was also, at one point, a rapper, In 2004, he gave an interview to Playboy, expressing his homophobia in terms that were almost hilariously direct:

I ain’t into faggots. I don’t like gay people around me, because I’m not comfortable with what their thoughts are. I’m not prejudiced. I just don’t go with gay people and kick it — we don’t have that much in common. I’d rather hang out with a straight dude. But women who like women, that’s cool.

2005: Kanye West speaks out against homophobia in hip-hop

Say what you like about Kanye's outsize ego and general jackassery, but he's one of the first hip-hop heads to really come out against homophobia. In a 2005 interview with MTV, West said that hip-hop was supposed to be about:

...speaking your mind and about breaking down barriers, but everyone in hip-hop discriminates against gay people... I want to just come on TV and just tell my rappers, tell my friends, "Yo, stop it."

In another interview, he noted that he used to be homophobic before learning that a cousin of his was gay. 

I would use the word "fag" and always look down upon gays. But then my cousin told me that another one of my cousins was gay, and I loved him. He’s one of my favorite cousins. And at that point it was kind of like a turning point when I was like, "Yo, this my cousin, I love him, and I've been discriminating against gays."

2006: Lil Wayne photographed kissing Birdman on mouth

In 2006, Lil Wayne, the cough-syrup-fueled dynamo who'd rapped about "homo niggas getting AIDS in the ass," was photographed kissing his mentor, Birdman, on the mouth. The pair have remained relatively tight-lipped on the kiss, though Birdman defended the kiss as familial a few years later, saying, "That's my son, ya heard me? If he was right here, I'd kiss him again."