Date: Feb. 10, 2010

During his now-infamous interview with Playboy, John Mayer made a number of racially offensive comments, amongst them a reference to his penis as being a "white supremacist" and seemingly flippant use of the "N" word when explaining the idea of a "hood pass." "It's sort of a contradiction in terms, because if you really had a hood pass, you could call it a 'n***er pass,'" Mayer said.

The immediate backlash to Mayer's controversial use of the word prompted him to issue an apology via Twitter, saying, "I am sorry that I used the word. And it's such a shame that I did because the point I was trying to make was in the exact opposite spirit of the word itself."

Mayer continued, admitting, "It was arrogant of me to think I could intellectualize using it, because I realize that there’s no intellectualizing a word that is so emotionally charged."