14. JENNA JAMESON

When: January 2011
Comment: “I don’t like the word raunchy. I’m irreverent and I say things that a lot of people wouldn’t say, and some of it probably isn’t in the best taste. But when I hear the word raunchy, to me that describes Jenna Jameson. Look, I’m never going to please everybody."

During an interview with Glamour, Chelsea described her comedic style and associated Jameson with the word raunchy. An angry Jenna Jameson eventually tweeted in retort, "Chelsea handler makes fun of peoples kids... Probably because she's a dried up old whore. Just cuz I say it like it is...... Don't hate...... She talks massive shit.. Ok, whatever...."