It’s hard to believe, but after 22 years, David Letterman is officially hanging up his late night shoes for good. Sure, we knew it was coming, but now the big day is finally here.
After Wednesday night, the Late Show is being handed off to Stephen Colbert (his first show airs Tuesday, Sept. 8), and Letterman is walking away from The Ed Sullivan Theatre for the last time. He’s told the press that he’s never going to set foot in that iconic New York building again. Excuse us for feeling a little nostalgic.
Before we say farewell to Letterman for good, we want to share the 22 things we’ll miss most about the iconic host and his legendary time on the late night circuit. Block off the next hour or so. And thanks for the memories, Dave.
1. His Top 10 Lists
Hard to believe they’ve been around since 1985, huh? So what started it all off? One of the most ridiculous lists of all: “Late Night’s Top 10 Words that Almost Rhyme with Peas.”
2. His original feud with Jay Leno
Everyone knows that Leno and Letterman were competing for the same Tonight Show gig during the earlier days of their careers (Leno swooped in and got the NBC show, forcing Letterman to leave the network and start up his own on CBS roughly a year later). It was a feud that spanned decades, but was never as succinctly addressed as it was when it was fresh in 1991. Exiting Late Night host Johnny Carson — who was advocating for Letterman as his replacement — flat out asked his guest: “Just how pissed off are you?” The real fun starts around the 3:30 mark.
3. His ongoing feud with Jay Leno
Letterman might have been classy when it came to Leno replacing him back in the day, but when Leno moved to 10 p.m. and Conan O’Brien took over — only to be fired so that Leno could come back a year later — Letterman couldn’t hold his tongue any longer. And with just one little monologue, the Late Night Wars were officially back on. No two hosts will ever duke it out the same.
4. The way he inspired guys like this
Hopefully the likes of Jimmy Fallon, Jimmy Kimmel and Stephen Colbert can inspire new legions of comedians that will reach this level of success too.
5. His stylish wardrobe
No one else could ever quite pull off a velcro suit the way Letterman could.
6. His scholarly, professor-ish ways
Who could forget the time he gave a Justin Bieber a geography test? His encouragement really was as fatherly as it gets.
7. That sauve way he has with the ladies
Um, a shirtless Drew Barrymore in 1995? We’d say that’s game if there was ever game to be had. The star, who was 20 years old at the time, flashed Letterman when she learned it was his birthday. The grin on his face had everyone thinking he might actually run for president after that.
8. The times he was just as uncomfortable as the rest of us — and it showed
What DO you do when Borat comes on and talks about his dead wife and liking to watch girls make pee?
9. How he always managed to draw in chaos
Andy Kaufman + Jerry Lawler = a recipe for disaster.
10. The fact that he’s a proud New Yorker, through and through
When 9/11 happened, it took a while for most people to find the words. Letterman took the lead, delivering one of the most emotional and heartfelt monologues to ever be broadcast. It put him on a whole new footing with audiences and fellow comedians alike.
11. That he owned up when he had to
How do you deal with an extortionist scandal that’s been leaked to the press? If you’re David Letterman you address the issue head-on, by telling your audience exactly what went down and admitting to having sex with members of your staff.
12. And he always thanked those that truly mattered
Letterman’s quintuple bypass surgery in the early 2000s gave everyone quite the scare. But there was no better episode than the one in which he returned. Between this opening monologue, Robin Williams dressed up as a doctor and the Foo Fighters playing Letterman’s favourite song, “Everlong,” the energy was infectious. “Wait ’til you hear what happened to me,” Letterman kicked it all off.
13. How he knew when to lighten things up with some good old fashioned physical comedy
Is there anyone who didn’t want to try on an Alka Seltzer suit at home and just float all their worries away?
14. We’ll miss interviews like this, when Letterman set the stage for a string of strange Joaquin Phoenix antics
There are actually no words.
15. We’re really going to miss Stupid Pet Tricks
This is high quality entertainment, people. Before cats and dogs took over YouTube.
16. Stupid Human Tricks, too
Eat your heart out, America’s Got Talent.
17. We always admired how he could admit to being an “asshole”
Why did it take Cher so long — four years to be exact — to appear on David Letterman’s show? Because she thought he was an “asshole.” Watch for the infamous comment around the 3:57 mark.
18. Paul Shaffer
We’d be remiss if we didn’t include Canadian band leader Paul Shaffer. He and Letterman were together for 33 years total; we’ll definitely miss him too.
19. How Letterman could party with the best of ’em
Devilled eggs, vodka and Martha Stewart. That’s how Letterman does it.
20. And how he could throw down in the kitchen, too
If you haven’t seen “David” and Julia Child improvise together over beef tartar, well … you haven’t lived.
21. His ability to know when to call it quits, and how to deliver an announcement in the most poignant way possible
We knew this retirement announcement was coming, but it still tugged at our heartstrings anyhow. This was the official beginning of the end.
22. And last, but not least, we’re going to miss one of the best guest-host relationships we’ve ever seen on TV.
On Wednesday night Letterman is ending it all exactly where it began — with Bill Murray stopping by as a guest star. The actor has appeared on more than two dozen episodes of the series throughout its run, making this final appearance a fitting end for a fabulous career.
Catch David Letterman’s final episode Wednesday, May 20.