25. Chelsea Handler
If the past, we've looked at Chelsea Handler's most controversial comments—if that wasn't enough to sway you, we'll spell it out for you: Handler says whatever is on her mind, and apparently her mind can be a vulgar, mean place.
Remember that in 2011, she pissed off the entire country of Serbia by coming to the defense of Amy Winehouse, who the Serbian Defense Minister had called a “shame and disappointment.” In response, Handler read the statement aloud during an episode of her E! show, Chelsea Lately, and followed it up with, “Well, so is your country.”
That's just one moment in a long career.