7. Letterman Has Fun With Conan/Jay Situation
You may remember back in 1993 that, when NBC gave Jay Leno The Tonight Show, it sent Dave to CBS to be his direct competitor. But the network walked into a similar nightmare in 2009 when it installed Conan O’Brien as host of The Tonight Show; fearing they'd lose the popular Leno to a rival, they created The Jay Leno Show at 10pm and generated considerable tension between the two hosts. Safe in his CBS perch, Letterman had a ball over the melee, trashing his former bosses and laying into Jay “Big Jaw” Leno in delicious monologues over several days. But some of his meanest barbs were hurled at the little-seen and culturally irrelevant Last Call With Carson Daly, which airs after Late Night. "Having a show at 1:30 is almost exactly like not having a show," Letterman said with wicked snideness.