Fail Occurred: April 23, 2009

While spending the day at Rutgers University, white stoner-cum-white rapper Asher Roth was, pardon the phrase, riding high. In that mindset, he tweeted, "Been a day of rest and relaxation — sorry twitter hanging with nappy headed hoes." He thought he was making fun of Don Imus; just about everyone else saw it as a retread of an ugly moment in time and race relations. The reaction was swift. His words were recycled and re-tweeted, and anger brewed up and down RSS feeds. Taste-making hip-hop site Nah Right banned Asher, and was criticized for not doing so earlier. After a few hours, Asher finally gave a fearful apology. No one's ever said it's easy being male, middle-class, and white.