A lot of talk show hosts celebrate their birthdays in April. Conan O’Brien just turned 50 years old, David Letterman is 66–but nobody’s having a better birthday than Jay Leno. He’s turning 63 years old while leaving The Tonight Show on his own terms. That’s pretty sweet revenge, since Leno frankly embarrassed NBC for allowing Conan O’Brien to usurp his late-night throne in 2009. The Tonight Show suffered in the ratings, Jay returned, and NBC made a real big production out of making sure American knows that new host Jimmy Fallon has the current host’s blessings.
Of course, we’ve all been assured that Jay’s not really cool as Conan. He’s certainly not as cool as Letterman. But The Tonight Show has always done better with younger demographics than people want to believe, and he’s even held up against Jimmy Kimmel–and we’re not particularly cool ourselves, so here’s three weird (and uncool) clips looking back at Jay’s career. We couldn’t afford to buy him another car….