Artwork by Cap Blackard (Buy Prints + More)

David Letterman is a once in lifetime entertainer whose worldwide pants straddled the classic days of late night television and the edgier wit of the modern era. He’s the missing link between the stylish Rat Pack bravado of Johnny Carson and the Dadaist outpouring of personalities like Conan O’Brien, Stephen Colbert, and even his own No. 1 fan Jimmy Kimmel. Not bad for a gap-toothed kid from Indianapolis who started as a TV weatherman.

Today, he’s a 68-year-old veteran. Most of his contemporaries have been replaced, changed formats, or are still secretly plotting their next sinister return from a luxury car garage in Burbank. By comparison, Dave’s the sole survivor. He’s going out on top and on his own terms, which is rare in any field, let alone the entertainment industry. Celebrities, musicians, comedians, artists, politicians, and fans of all ages have made pilgrimages to the Ed Sullivan Theatre to spend one final evening with their late night hero.

Tonight, it’s all over. Which is why we’re taking a closer look back at how it was even possible for one funny man to shape so much of our world. Ahead, you’ll find a comprehensive editorial spread out over three unique sections, which we’ve broken down into a simple menu for you to peruse below. Think of it as a breezy guide to a complicated icon, or treat it as an online celebration, culled together by a collection of writers who really, really, really wanted to talk about Dave.

So, pop the champagne, find an old pencil, and start tapping away.

I. The Humanity of David Letterman

II. Top 10 Late Night/Show Performances

III. 33 Years, 33 Essential Memories