Fact #1: Jay Leno has been the most popular late night host in America for the majority of the past 19 years.
Fact #2: Comedians, Hollywood insiders, and laypeople alike just love hating on Leno, and have been doing so consistently for over 20 years.
Why? In their minds, the reasons are legion: Because he stole The Tonight Show from Johnny Carson’s rightful heir, David Letterman, way back in the early ’90s. Because he refused to simply retire when NBC tried to replace him with Conan O’Brien in 2009. Because his primetime Jay Leno Show tanked, sinking Conan’s Tonight Show before it had even really begun — and eventually forcing Conan to leave NBC for good. And most of all, because they say his jokes are broad, pandering, and eminently unfunny — which is a shame particularly because once upon a time, Leno had a reputation for being one of standup’s sharpest and edgiest comedians.
So as Leno prepares for his final few Tonight Shows, he finds himself in a unique position: More widely watched than any of his competitors, yet widely reviled by the majority of his peers. How widely, you ask? Let’s take a look back at the most notable jabs, slights, and straight-up insults famous people have aimed at Leno over the years — starting shortly after NBC revealed that he, rather than Letterman, would become Tonight‘s next host. (Insert “Jay takes it on the chin” joke here.)