Happy 30th anniversary, Letterman. Oh, and I love you.

I have the oddest crushes: Alex Trebek, Wolf Blitzer, David Letterman …

When I started watching Letterman, he was smoking cigars on air. It was late-night and it was different from anything else on television. The show had an underground-cool factor. They booked the coolest music acts and some of New York’s most notorious notables. From the get-go, the brass at NBC were grooming Dave for the much coveted 11:30PM spot, once Johnny Carson – Letterman’s mentor – decided to retire.

But television is cruel. It’s a business where you recognize your friends from your enemies because they stab you in the chest and not in the back. And when it was time to pass the baton, NBC decided to hand it to the King of boring, the Master of predictable, the Lord of note-cards-during-interviews: Jay Leno. No need to sugar-coat it: Letterman had been fucked.

In his book The Late Shift, Bill Carter describes a depressed Letterman, ready to give everything up. It was Johnny Carson who convinced him to not quit late night television and to accept CBS’ lucrative offer. And he did. And then thrived, reminding us all that sometimes, Plan B is the better plan.

Letterman is more than a talk-show host and more than a pertinent interviewer. He’s a raconteur, a fan of indy bands and of Darlene Love, a geopolitical connoisseur even if he modestly tries to dumb himself down. Beyond the laughter, it’s Letterman’s sensitivity that often prevails. Never was that more true than in the wake of September 11th 2001.

Here’s Letterman, on the first show after the tragedy: