Top 10 Moments From the ‘Late Show With David Letterman’

Lauren Novak August 30, 2023

LATE SHOW WITH DAVID LETTERMAN, David Letterman, (Season 21, Episode 114, aired April 3, 2014) — Jeffrey R. Staab/CBS/Everett Collection

David Letterman will likely go down in history as one of the most popular talk show hosts of all time. He moved to CBS and fronted The Late Show with David Letterman starting on August 30, 1993.

LATE SHOW WITH DAVID LETTERMAN, David Letterman, 1995, 1993-2015

Christopher Little/CBS/Everett Collection

As we celebrate the show’s 30th anniversary, let’s go over some of the best moments until its eventual end in 2015, with Stephen Colbert taking over after that. In recent years, Letterman has hosted the Netflix series My Next Guest Needs No Introduction with David Letterman and That’s My Time with David Letterman.

Barry White and His Top-Ten List

No doubt the Top Ten list you’re reading right now was inspired by Letterman’s famous Top Ten lists. Many different guests presented the segment over the years and one of the best was done by crooner Barry White. You can’t help but laugh at the absurdity of the top 10 words that sound romantic when spoken by Barry White, complete with ’70s-style background singers. If you have some time, watch as many Top Ten lists as you can because it was no doubt one of Letterman’s best segments.

Letterman’s Mom and the Olympics

It seems that we know where Letterman got his comedic chops from. His mother Dorothy appeared several times on the show and famously traveled to Lillehammer, Norway for the 1994 Winter Olympics. She was so sweet and fans loved it when Dorothy popped up in one of the segments. She passed away in 2017.

Chris Farley has an unusual entrance

Just a few years before his untimely death, actor and comedian Chris Farley appeared on the talk show to promote his film Tommy Boy. Always the jokester, he entered the interview by doing cartwheels and rocking out to the music. The pair interacted so well and were so hilarious that many fans commented that it was one of the rare interviews that got Letterman laughing so hard.

Letterman works at Taco Bell for a day

This is a pretty common segment among talk shows now but it was pretty unique back in the day. Letterman decided to spend one day working at Taco Bell, working the drive-thru, to see what kind of reactions he would get. Of course, he jokes around and even pulls pranks on customers, making it an awesome day for surprised fans and Taco Bell employees. He also worked at McDonald’s for the day.

Drew Barrymore leaves Letterman speechless

In a 1995 appearance on the show, Drew Barrymore gave Letterman an interesting present for his birthday. She did a dance on the desk and even flashed him. It was one of the rare moments that he was speechless and proved that anything can happen on late-night television.

Joaquin Phoenix’s bizarre appearance

Joaquin Phoenix was perhaps the most controversial and talked about guest on the CBS show. It was so uncomfortable and he appeared unshaven, quiet, and just downright odd. It ended up being a stunt for Phoenix’s mockumentary called I’m Still Here but Letterman truly didn’t know that. At the time, people thought he had lost his mind but it ended up being a way to mock Hollywood. Now that people are in on the joke, many find the whole thing hilarious and thought-provoking.

Letterman’s monologue after 9/11 attacks

Let’s get serious for a moment. Many television shows stopped airing the night and days after 9/11 and comedy talk shows were nervous to get back on the air after such a major tragedy. Letterman decided to continue with the show and shared a very honest and heartfelt monologue that resonated with a lot of people.

Johnny Carson’s final appearance

Johnny Carson was a personal hero of Letterman and Carson’s last television appearance was on the Late Show. Carson took over Letterman’s desk and read the Top Ten for him and it was just a heartwarming moment of television.

Stupid Pet Tricks

This segment featured animals doing bizarre and often silly or cute tricks. Think dogs playing basketball, pigs eating mints, and skateboarding bunnies. Letterman would often say “Remember, this is not a competition, it is only an exhibition — please, no wagering.” This segment also extended into Stupid Human Tricks at times.

Outdoor stunts

Letterman used to do some fun outdoor stunts from time to time outside of the Ed Sullivan Theater, where the show was taped. Some of these were pretty wild! Tell us, what is your favorite moment from Late Show with David Letterman?