The Top 10 David Letterman Moments
In his 33 years on late-night television, David Letterman hosted 6,028 episodes of Late Night (NBC) and The Late Show (CBS), and was the longest-running late-night broadcaster in American history. We at Esquire have certainly missed his now-bearded face and are happy to hear he’ll be returning to entertain us for a new series for Netflix.
The yet-to-be-named, six-episode series has Letterman combining two of his areas of forte: in-depth conversations with extraordinary people, and in-the-field segments where he’ll able to express his amicable sense of humour. In each hour-long episode, Letterman will conduct a long-form conversation with a singular guest - and will also explore topics on his own, away from the studio. The series is set to premiere in 2018.
To commemorate the return of Letterman to our screens, we thought it best to take a trip down memory lane and have a look at some of the host’s most memorable moments.
1. Joaquin Gets a Little Weird
You remember when Joaquin Phoenix went through that phase of being an absolute weirdo in order to accumulate footage for his mockumentary I’m Still Here? Letterman remembers.
2. Letterman Confesses To Having An Affair
When you’re a figure as famous as David Letterman it’s rare that your private life ever remains truly private. Subject to an extortion plot regarding the intimate details of his life, Letterman, aware of his dirty laundry already being aired for all to see, exhibited an overwhelming honesty by announcing to viewers all over the world about his numerous extra-marital affairs with members of his staff.
3. Michael Richards Apologises
After a video of Michael Richards (known for his performance of Kramer on Seinfeld) delivering a wealth of racial slurs to hecklers went viral in 2006, Richards made the decision to appear via satellite on the Late Show in order to attempt to apologise for his actions. Replete with uncomfortable laughter from the audience, this moment remains one of the most controversial interviews that Letterman has conducted.
4. Jimmy Carter Talks About His Great-Grandchildren
It’s not often that someone gets to interview the President of the United States, and it’s even less often that someone gets to do it multiple times throughout their career. Although there are multiple Letterman presidential interactions to choose from, we found his interview with the former president Jimmy Carter to be one most endearing and interesting.
5. Andy Kaufman vs Jerry Lawler
The world of professional wrestling is pretty insane. Often blurring the lines between fiction and reality, it can sometimes be quite difficult to differentiate between the two. There’s nothing that better conveyed the absolute madness of the sport than that of surreal scripted rivalry between comedian Andy Kaufman and professional wrestler Jerry Lawler. Transporting their conflict onto Letterman’s show in 1982, not only was this a landmark moment in the world of wrasslin’, but it’s also a fantastic precursor to the “reality” of reality television we’ve become accustomed to today.
6. Letterman Grills Paris Hilton Over Jail Time
David Letterman is a man used to interviewing a range of the world’s most talented individuals. So when the slightly less talented Paris Hilton appeared on The Late Show to promote her latest perfume range, you knew that Letterman wasn’t going to go easy on the hotel heiress. Watching David Letterman rip apart Paris Hilton over her stint in jail is a little like watching a pride of lions tear apart a gazelle. You know what you’re watching isn’t really a fair fight but you simply can’t take your eyes off the action for even a second.
7. Warren Zevon Gives His Final Performance
After his good friend and frequent guest Warren Zevon was diagnosed with terminal lung cancer, Letterman dedicated an entire episode to the musician and his ongoing battle with the disease. This episode not only gave viewers an incredibly human insight into the transience of life (complete with Zevon’s wonderful life advice of “enjoy every sandwich”) but it also offered a touching final public performance from the iconic musician.
8. Letterman Meets Bieber
Towards the tail-end of his tenure you could definitely tell that David Letterman was getting a little tired of some of the supposed “celebrities” he had to interview. In so situation was this more pertinent then when Letterman met Bieber in 2012 and proceeded to mock the poor young lad for all he was worth. Whilst Letterman’s belittling of the Biebs might seem overly harsh at times, this video is worth a watch purely for Letterman’s uttering of the phrase “chicks ahoy”.
9. Drew Barrymore Wishes Letterman a Happy Birthday
Yeah, you all knew this one was coming. Who could forget about the time that a then-20 year old Drew Barrymore decided to wish David Letterman a very happy birthday in just about the best way possible? We certainly haven’t. Happy birthday, Dave indeed.
10. Seinfeld’s Last Time on Letterman
A regular guest on the show over the years, we’re pretty sure everyone got a little emotional when Jerry Seinfeld returned for one final appearance with Letterman in April 2015. Performing the very same stand-up routine he did all the way in 1982, this was a fitting way for Seinfeld to pay tribute to Letterman’s legacy and the numerous high-profile careers he’s helped to jumpstart over the years. Jerry and David even have a go at doing the classic Letterman run for old time’s sake.