Angelina Jolie

• 2005: Trump demeaned the physical attractiveness of Angelina Jolie while speculating on MSNBC about the celebrity divorce of Brad Pitt and Angelina Jolie. “What good is a celebrity split without two-time divorcee Donald Trump to weigh in on the matter? Fewer than five days before his own nuptials to wife No. 3, Trump had more than a few things to say about Brad and Jen's breakup, telling msbnbc.com: ‘There are plenty of rumors about why they split. Maybe Jennifer was jealous that Brad got too friendly with his co-star, Angelina Jolie. ‘Now I never really understood that one because I watched Angelina Jolie with Billy Bob Thornton, and she was all over the guy.... I mean, do people really dig her?’ Five words for Trump: Esquire magazine's sexiest woman alive.” (Chicago Tribune, January 18, 2005)
• 2007: Trump again publicly criticized Angelina Jolie's appearance, claiming in an interview with Larry King that she was not "beautiful." “What do you do if you're no longer one of the biggest names in Hollywood? If you're Donald Trump, you attack one of the biggest names in Hollywood. The target? Angelina Jolie. The subject? Are you ready for this? Her beauty. ‘I'm not saying she's an unattractive woman, but she's no beauty, by any stretch of the imagination,’ Trump said earlier this week on ‘Larry King Live.’ ‘In terms of beauty, she's not a great beauty. She's a nice-looking woman. She's OK. But she's not a great beauty.’” (Chicago Tribune, October 19, 2007)