As Leno prepares to hang up his Tonight Show spurs Thursday night, let's look back on some of the highlights of his decades-long tenure, from his news-making interviews to his 4,600 jokes about Bill Clinton:
That Hugh Grant Interview
After winning a nasty war of succession with David Letterman, Jay found himself trailing his old rival in the ratings, until one perfect question – "What were you thinking?" – launched him into first place, a position he'd hold for more than a decade.
The Dancing Itos
Jay got a lot of mileage out of the O.J. Simpson trial, but none of his skits were more bizarrely enjoyable than this troupe of flamboyant Lance Ito impersonators.
Steve Irwin's Appearances
Letterman had Jack Hanna for longer, but Leno had the freewheeling Irwin, who brought a madcap enthusiasm to the placid Tonight Show set.
His Post-9/11 Show
The L.A.-based Leno didn't – couldn't – have the emotional reaction to 9/11 that New Yorkers David Letterman and Jon Stewart did, but in the turbulent weeks after the attack, Leno's dependable professionalism was its own kind of salve.
Ask the Fruitcake Lady
Did you know she was an aunt to Truman Capote? Like her literary nephew, Marie Rudisill tempered a caustic wit with just enough Southern charm to take the edge off.
Arnold Schwarzenegger Vows to 'Pump up Sacramento'
It was one of those moments that will make future generations sit up and go "really?" A strongman actor with no political experience goes on national television to announce he's running for governor of America's most populous state. Arnold's bid became international news (as you can see in the clip above) and it all happened on Leno's couch.
Is it the most original segment? No, but Jay made it his own, with a winking roundup of the foibles of America's small-town newspaper editors that he delivered with relish.
Alongside "Headlines," this is the segment that most viewers will remember Jay's Tonight Show by. Was it a searing critique of the American education system, or just a study in how performance anxiety affects the temporal lobe? Why not both?
The man who will inherit Leno's seat has made his career on a series of viral-ready sketches, but Leno proved he had it in him too, when this impromptu karaoke segment spread around the Web in 2013.