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The Top 10 Memorable Moments on Letterman

A look back at the most memorable moments from the past 30 years of Late Show with David Letterman, including his interviews with celebrities like Bill Murray and Dolly Parton, his tribute to Johnny Carson and his opening monologue after the 9/11 attacks. 

Photo of David Letterman and his son Harry, with Love quote

You may have heard, David Letterman is ending his gig behind the desk of CBS’ Late Show this week. To commemorate the 30 years he’s been a part of the TV landscape, we’ve put together our own “Top Ten” list of the funniest sketches, greatest celebrity guests and most memorable moments on the show.

10. Julia Child’s Cooking Lesson 

Chef, author and TV star Julia Child frequently visited the late night set to whip up something special for Letterman. The two bantered together like old friends and usually, the dish came out perfect (it’s Julia Child after all). But during one cooking segment, when Child was teaching Letterman how to make hamburgers, of all things, the show’s cooking equipment malfunctioned forcing the chef to think quickly on her feet and giving the audience a good laugh. There’s a wonderful story about a later appearance of Child’s when she made her Bananas Foster recipe and Letterman requested that she make an entrée for him, instead. Her response: “You tell David Letterman not to be so fussy. He’s not the Queen of England, you know.”

9. The Suits Sketches

Before the internet meant late night show sketches could go viral, before Jimmy Fallon was parodying Game of Thrones or James Corden was singing in a car with Jennifer Hudson, Letterman was creating funny bits that oftentimes only his studio audience and the viewers at home got to see. One such skit was his recurring suits sketch, which had the host trying on all manner of wacky wear. From being covered in Alka-Seltzer tablets and dropped into a tank of water to wearing Velcro and sticking himself to a wall, Letterman was never afraid to poke fun at himself in order to give us a laugh.

8. Warren Zevon Interview

Rocker Warren Zevon was one of Letterman’s favorite guests. Along with performing great music, the singer also gave a really good interview, full of witty comebacks and self-deprecating jokes. Zevon performed on the late night talk show over a dozen times and even filled in for late night band leader Paul Shaffer on occasion which is why, when Letterman learned of the artist’s cancer diagnosis, he devoted an entire show to him. The two talked about his prognosis and Zevon gave a memorable piece of advice to Letterman and his audience: “Enjoy every sandwich.” That show would turn out to be his last public performance. Zevon died a year later.

7. Dolly Parton Interview

Dolly Parton came onto the Letterman show many times throughout its run but one of her first interviews with the host was back in 1989 when she came on to promote her film Steel Magnolias with Julia Roberts. The singer and actress talked about her upcoming tour and joked with Letterman about her love of food and her first time visiting the Big Apple.

6. Teri Garr Interview

Actress Teri Garr was a favorite of Letterman’s and was often on the show. The two flirted and joked with each other, but Letterman’s affection for the star really showed when he had her on for what would be her final TV appearance in 2008. Teri had recently had a brain aneurysm but agreed to do the interview with Letterman anyway, and the host sweetly walked her to her chair when she first stepped in front of the camera. The moment proved chivalry wasn’t dead and that Letterman could, in fact, be a gentleman.

5. Oprah And Dave Bury The Hatchett 

The much-talked-about feud between Oprah Winfrey and David Letterman supposedly began when Winfrey graced the late night show in the ’80s and had a not-so-pleasant experience. It would be another 16 years before she came back, but when she did, the actress and former talk-show host addressed all of the rumors of bad blood between the two. Letterman and Winfrey jokingly buried the hatchet and the host was even kind enough to escort Winfrey across the street to the opening of her Broadway musical, The Color Purple.

4. Johnny Carson Tribute

Johnny Carson will always be the true king of late night television and Letterman acknowledged that when he invited Carson onto his show for what would become the former late night host’s final TV appearance. Carson didn’t say much, but in a beautiful gesture of respect and friendship, Letterman let him sit behind his own late night desk and invited him to participate in his Top Ten skit. After the icon’s passing, Dave would give an emotional tribute to the man he so admired.

3. Bill Murray Interview

We have to think that any interview with actor Bill Murray would be a fun one, but Letterman’s first encounter with the star—which also happened to be his first celebrity interview ever when he initially took his seat behind the desk at NBC—is one of his most memorable. The comedian broke out into song, missed the first half of the show and didn’t mind picking on the show’s host a bit. The two enjoyed the experience so much, Murray would go on to guest on Letterman’s show for years to come.

2. Paul McCartney Concert

Artists regularly gave concerts on top of the famous Late Night marquee, but no performance was quite as memorable as Sir Paul McCartney’s. The Beatles singer played to a crowd that packed the sidewalks and filled the streets in front of the Ed Sullivan theater.

1. Dave’s 9/11 Monologue

In his first show after the terrorist attacks of 9/11, Letterman gave a poignant monologue trying to make sense of what had happened in his city and across the nation. Skipping his usual zinger-filled opening, Letterman praised then-Mayor Rudy Giuliani, members of the police and fire departments, and the hundreds of rescue workers who bravely risked their own lives to help save others. Letterman ended his speech with these words, “If you didn’t believe it before, you can absolutely believe it now. New York City is the greatest city in the world.”

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