3. Roger Ebert
Date: Jan. 5, 2011
For centuries, the tale of Huckleberry Finn been mired in racism. Ebert shared his thoughts on the modern version of the novel in the most indiscreet way possible, tweeting: "I'd rather be called a N***** than a Slave." That didn't go over so well. He later tweeted, "You know, this is very true. I'll never be called a N***** *or* a Slave, so I should have shut the **** up." Thumbs down, homie.