Top 10 David Letterman Moments

By Julia Ricci

We all knew it was coming sooner or later, but the world was shocked April 3 when David Letterman suddenly announced that he will retire in 2015. Letterman has been a prominent figure in television for more than 30 years, and it’s going to be sad to see him go. It’s not time to be too mournful just yet, however, so let’s reminisce on his career with the Top 10 David Letterman Moments. Ready, Paul?

David Letterman announces his retirement on April 3, 2014.

10. The first top ten.

    After Letterman delivered his inaugural Top Ten “Words That Almost Rhyme With Peas” on September 18, 1985, listing things in a category has never been the same. Top ten lists were nothing new at the time, but Letterman’s famous absurdist humor gives them a fun spin and has made them a timeless fixture in pop culture.

9. Any time “Jungle” Jack Hanna was a guest.

    “Jungle” Jack Hanna’s numerous appearances on Letterman’s late night programs have provided some of their funniest and most unpredictable moments. The interactions with the animals were always great, but Hanna and Letterman’s rapport and Hanna’s mock-exasperation any time Letterman asked an honest question made these segments all the more enjoyable.

8. Working the drive-thru.

    It’s a shame Letterman stopped doing remotes; he’s absolutely hilarious in them, especially when he worked the drive-thru windows at McDonald’s and Taco Bell. These segments are a testament to his quick-thinking comedic chops and sarcasm and are always a delight to watch.

7. The annual tradition of Darlene Love performing “Christmas (Baby Please Come Home).”

    Singer Darlene Love has been performing this Christmas classic for Letterman since 1986. It’s always a spectacle with a huge band and backup singers, and the perfect way to kick off the holiday season. Last year’s performance was the best yet.

6. The episode sans-audience during Hurricane Sandy.

    While most of New York City shut down due to Hurricane Sandy, David Letterman and bandleader Paul Shaffer still put on a show with a handful of crew members and no audience. The silence was eerie, but the show was still entertaining, and the most endearing moment came when the Top Ten was presented on cue cards instead of computer graphics.

5. Oprah’s 2005 interview.

    This interview marked the first time Oprah had appeared on Letterman in 16 years after a supposed feud between the two. Conflict or not, they had a good conversation, and afterward Dave escorted her across the street to a performance of the Broadway version of The Color Purple she produced. Seven years later, he’d bring her to Ball State.

4. Dave’s return after his heart surgery.

    After undergoing quintuple bypass surgery, Letterman returned to The Late Show on February 21, 2000. He cracked a few jokes about it in his monologue, but he got choked up when he brought out his medical team, saying, “If you ever have to have this surgery, by God, I hope you’re blessed enough to go through it with people like these.”

3. When Bill Murray does anything.

    The enigmatic Bill Murray was Letterman’s very first guest way back in 1982 and has paid many memorable visits since. Each time he returns with a stunt bigger and more bizarre than the last–from dumpster diving (literally) to flying onstage as Peter Pan. Murray has been a feature of Letterman’s shows since day one, so I wouldn’t be surprised if he returns for the final send-off.

2. The post-9/11 Monologue

    On September 17, 2001, The Late Show was the first late night program to return after the 9/11 attacks. Letterman delivered a solemn monologue from behind his desk, praising then-mayor Rudy Guiliani and the first responders. He cracked a few little jokes to alleviate the tension, but he also expressed the anger, confusion, and sorrow everyone was feeling and handled it in a heartfelt, honest way.

1. “Are these your drums?”

    On a happier note, this has been a running joke of Letterman’s for quite some time and he’s asked this question of just about every drummer in the bands that perform on the show. We may never know the reason behind it, but it sure makes a good super-cut.