8 David Letterman Moments That Will Really Make Us Miss the Late Night Icon

The long-time late night host takes his final bow tonight at 11:35 p.m. on CBS

By Lauren Piester May 21, 2015 12:30 AMTags
David LettermanJeffrey R. Staab/CBS ©2015 CBS Broadcasting Inc. All Rights Reserved

One of the most reliable staples of late night is taking his final bow tonight after thirty-three years, and it feels like we're losing a relative or a dear old friend. He's not dying, of course, so it's more like he just decided to move to Florida, but in any case, we're going to be going from seeing David Letterman every single night to seeing him maybe a few times a year, and that's definitely going to take some getting used to. 

While thirty-two years of interviews and segments and musical guests is a lot to go through, we've attempted to compile some sort of a list of moments that are really going to make us miss TV's late night icon, the man who changed the face of talk shows for good.

Justin Bieber's fans thought Letterman was being rude when he grabbed Justin's arms and made fun of him for referring to the Sistine Chapel as the Sixteenth Chapel, but this whole thing is really just a more public reenactment of any interaction between any grandpa and a teen boy relative at a family gathering. "So you're 18 now? Are you gonna vote? Will you go to college? Don't get any more tattoos!" Maybe if Justin had actually had a grandpa like David Letterman, he wouldn't have gotten in so much dumb trouble over the years. 

Back in 2008, during his presidential campaign, John McCain was supposed to appear on the show. He canceled at the last minute, saying he had to rush back to Washington, but then it was discovered during the taping of the show that he was still in New York, preparing for an interview with Katie Couric. Needless to say, Letterman was not thrilled and went on a beautiful tirade before wondering if the senator would ever come back. 

Strangely, McCain did come back to the show, and had no defense other than three words he repeated over and over again: "I screwed up." 

Watch: Bruce Willis Shares Bizarre "DWTS" Story on Letterman

Bruce Willis has often had a habit of showing up on the Late Show with weird hat and an even weirder story, and his last appearance was truly special. He not only recreated his look from his very first appearance on the show, but he told a strange story in which he had to break up a fight on Dancing with the Stars, and either Julianne Hough or Carrie Ann Inaba kicked him in the head. 

Joaquin Phoenix's appearance in 2009 is the stuff of legend and brings the art of trolling to a whole new level. He donned sunglasses inside the theater, claimed he was retiring from acting to start a hip hop career, and prompted Dave's famous quip, "Well Joaquin, I'm sorry you couldn't be here tonight." It was glorious, and it only got better when we learned that it was all a stunt for another movie. 

"Howdja like being in jail?" Letterman asked that to Paris Hilton right after her jail stint in 2007 as casually as he asked if she liked New York or LA better, and it was a truly beautiful moment in pop culture. 

After Johnny Carson died in 2005, Letterman opened his show without a single mention of the death. However, after his monologue, he revealed that the whole monologue was actually written for him by Carson. It was a beautiful tribute for one of the greatest minds the comedy world has ever seen. 

We will never, ever forget Crispin Glover's bizarre 1987 appearance on the show in which he shocked both the audience and Letterman himself by his demeanor. He almost kicked the host in the face! What. Did. We. Just. Watch.

What was your favorite moment from Letterman's career? Sound off in the comments section below!