Everything had to go wrong for Jimmy Fallon to get The Tonight Show. NBC had to choose Leno over Letterman, and then choose Leno again over O’Brien: A pair of historic injustices, if you’re the kind of person who treats millionaire-white-dude desk-swapping like generation-defining culture-quakes. There’s a school of thinking that Letterman and O’Brien “deserved” The Tonight Show — not to mention two decades of jokes about how Leno didn’t deserve it. But deserve’s got nothing to do with it. The Tonight Show is a powerful concept — a way to talk about Hollywood or America or Comedy or Whatever Matters Now — but it’s also a straightforward piece of old-fashioned showbiz, a variety show airing five times a week on a network that needs to make money.
Letterman and O’Brien always had a perspective on the late-night franchise that was simultaneously admirable and totally weird: They seemed to buy in completely to the grand idea of The Tonight Show, but also want more than anything to stamp themselves completely onto that grand idea. As related in Bill Carter’s The War for Late Night, O’Brien could have actually kept The Tonight Show but refused to move it back to midnight. Four years later, it’s hard to tell whether that exit was a brave blow struck in the eternal battle of Individual against Machine, or a defining moment in the history of Taking Things Too Seriously. READ FULL STORY