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Celebrating the end of an era: 4 shocking moments with David Letterman

After over 30 years in the business, legendary talk show host David Letterman is finally retiring from the "Late Show." The last show airs May 20. According to Time magazine, Bill Murray is Letterman's last scheduled guest, appearing the night before, which means the events of the last show are largely still a mystery. 

As for who will stay tuned for the hosts final bow, a recent Opinion Outpost poll showed that roughly 31 percent of viewers plan to watch the last performance.

Whether you're a Letterman fan or not, it's hard to deny this talk show host's success. His shows have been filled with wholehearted laughs, punchy dialogue, exciting bits and even a few breathtaking moments. 

Here are 4 of the most shocking examples.

4. Madonna drama
One of the music industry's most popular artists squaring off against a quick-witted talk show legend, Letterman's interview with Madonna in 1994 was bound to be entertaining, but it jumped into legendary territory after Letterman's introduction.

"She's sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry," Letterman ribbed.

Madonna fired back by smoking a cigar and saying the F-word a record 14 times on air. If that interaction doesn't shock you, think about how the FCC reacted.

3. Every Bill Murray appearance
Murray has a special legacy on the "Late Show." Nearly every appearance he's made with Letterman has been bizarre and eventful. Vulture has cataloged some of his stunts. Murray has dressed up as Peter Pan and flown onto the stage. He faked his own kidnapping. He let Letterman shave his beard just because he felt the urge to change his appearance. He dressed up as Liberace. And, don't forget one of his most memorable quotes on his first ever visit with Letterman. He told the host:

"You got out of Indianapolis and didn't look back. I'm just waiting for the other shoe to fall on you, man, and I want to be there when it hits the floor! I had a chance to strangle Richard Nixon and I didn't—and I regret it!"

2. Tina Fey's #LastDressEver
One of his last guests on the show, Tina Fey quipped about how she wore fancy dresses on the "Late Show" as a sign of respect to Letterman. Her point was that after his retirement, there would be no reason to wear a fancy dress again. Her next move: strip down on-stage and give her clothes to Letterman. 

1. Johnny Carson's surprise appearance
When one of the figureheads of the late night talk show medium pays a visit to your set, that's when you know you've made it. Johnny Carson made a surprise appearance in 1994, but didn't even get the opportunity to make a joke during his time on stage. The crowd went wild for the retired hosting legend and refused to stop. He left his spot at the desk behind a thunderous applause without ever saying a word.

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