After a bare-knuckle fight to get the job, then 17 years on the air (almost all at #1) – the most famous chin in America is leaving one of the longest television institutions: The Tonight Show. During that time, Jay managed to log 33,000 political jokes and hundreds of guests. While many people in my generation have mixed feelings about Leno’s humor, I’ve routinely enjoyed his overstuffed monologue and moreover, his workaholic attitude and good humor about the seedier parts of the business.

He will be missed, but not for long: as you probably know, NBC has gambled that Jay’s older audience will watch him nightly at his new 10:00 slot – and with any luck, the college crowd tokes up early and decides to stay glued to the Peacock from 10 all the way to 2:30am. To help bridge the gap, new host Conan O’Brien will be the final guest on Jay’s show (with music by James Taylor).

We’ll have to wait ’til the fall to see how the 10pm gig works out. Either way, his run on The Tonight Show certainly is a great accomplishment. Here’s to you, Jay.

Now, a look back at some moments that didn’t go as planned:

UPDATE: The Hollywood Reporter has a really good, albeit a bit technical, take about how Jay could succeed from a business-sense at 10pm. As I’ve said countless times, even though it’s a huge gamble, this could be the best move by network TV since the dawn of cable.