Top 10 Most Controversial Moments From 'The Late Show With David Letterman' — VIDEOS

It is the end of an era. I feel like I've been saying that a lot with regards to television lately, but so many shows are experiencing a change in hosts and casts that it never stops being true. David Letterman's final Late Show appearance will happen on Wednesday night, a gig that will be taken over by Stephen Colbert in a post-Colbert Report world, and nostalgia is the name of the game as a result. While we've already said our goodbyes to, and made peace with the end of, The Colbert Report, it's time to give that same amount of love and Kleenex to The Late Show. Specifically, it's time to take a look back at some of the most controversial moments in The Late Show with David Letterman's history, because, well, there have been a lot of them.

Say what you want about Letterman, but he is an envelope pusher. Sometimes, that's good, and it results in a hilarious and spot-on interview that we couldn't get on any other late night talk show. Sometimes, that's bad and results in him putting his foot in his mouth so completely that you can't watch the interviews in question without cringing. And that's not just limited to the show itself. Letterman as a person is an institution, so his actions outside of the show tend to affect how people view it, and him.

In honor of Letterman's beloved Top 10 Lists, here's a Top 10 List of the Most Controversial Late Show Moments.

1. David Letterman Vs. Oprah Winfrey

It was the feud heard 'round the world. Letterman is a staple of late night talk shows, and Oprah is a staple of daytime talk shows, so, when the two began feuding, everyone was choosing sides and watching with a bag of popcorn. The feud, which lasted for 20 years, began when Winfrey made what she described as an "uncomfortable" appearance on The Late Show, which made her refuse to be a guest on the show again. Letterman began cracking jokes about this, and Winfrey didn't speak to him for 16 years. While aspects of the feud were probably exaggerated, it is rather famous at this point. Thankfully, the two have since buried the hatchet.

2. David Letterman Isn't Picked As Johnny Carson's Replacement

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Remember when Johnny Carson shocked the world by retiring from The Tonight Show after almost 30 years? By that time, Letterman, a close friend of Carson's, had covered for him on the show a grand total of 51 times — so he was the obvious choice to take over the chair when Carson retired. Right? Wrong, because the spot was given to Jay Leno instead. Suffice it to say, it's a good thing that worked out.

3. David Letterman Vs. Madonna

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Let us never forget the time that Madonna appeared on The Late Show and dropped so many f-bombs that there aren't any left to put in the script of your average Kevin Smith movie. At the very least, it certainly kept Madonna's name in the papers — and is still being talked about even now.

4. Drew Barrymore Flashes Letterman

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Was it real? Was it scripted? Either way, it is definitely a thing that happened.

5. The World's Most Awkward Janet Jackson Interview

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Ah, the Super Bowl. A time of freedom and spectatorship and... Justin Timberlake ripping off a portion Janet Jackson's shirt. The two pop stars got in a lot of trouble for the incident, which was controversial in its own right, but let's not forget the immensely awkward interview that Jackson did on The Late Show not long after. She so clearly doesn't want to talk about this. Letterman so clearly doesn't care. Awkwardness ensues.

6. David Letterman Vs. Bill O'Reilly

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Letterman and O'Reilly have... certain differences in political opinions. I think it's safest that we just leave it at that.

7. The Sex Scandal

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It's one thing to be dealing with a sex scandal for having affairs with his female staff members. It's another thing to be dealing with blackmail over that same scandal. But it's on a whole other level to publicly admit to the scandal, and to the blackmail, and then to use your late night show to discuss it and apologize to your girlfriend. Only on Letterman, you guys.

8. David Letterman Bombing At The Oscars

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When Letterman got to host the Academy Awards in 1995, I don't know what the world was expecting, but it definitely wasn't that. His jokes fell flat, and then kept falling flat, and his performance there bombed so hard that it allegedly began to affect the ratings of The Late Show. (Side note, he also used the time to take a couple more digs at Oprah Winfrey. Just saying.)

9. David Letterman Vs. Jay Leno

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Ah, Letterman and Leno. The feud that began when Leno got The Tonight Show spot over Letterman, and continued on for years. Although the two used to be very good friends, "The Late Night Wars" put a huge dent in that friendship — allegedly. While Leno and Letterman were said to have achieved frenemy status, neither of them really had negative things to say about one another in the press or anything. So, as far as feuds go, this one was pretty boring.

10. The Final Show Announcement

Suffice it to say, people are still really upset about this. However, the announcement that Stephen Colbert will be taking over The Late Show after Letterman was enough to mollify a few grieving fans. A few, but not all.