10. Paris Hilton meets David Letterman (2007)
Three months after her infamous prison stint, the allegedly new and improved Paris agreed to appear on The Late Show With David Letterman, ostensibly to promote her new fragrance. The host's opening question? "Uh, how'd you like being in jail?" "Not too much," replied Paris,  before squirming her way through a further six minutes of grilling about life behind bars - with precious little mention of her signature scent. How rude!
Dive-behind-a-cushion moment: At one point, a member of the audience called out, "I love you, Paris!" Glad of the distraction, the heiress called back, "I love you, too" and blew a kiss. "Somebody you met in prison?" asked Letterman.