The Top 10 Times David Letterman Got Too Real

3. Johnny Carson Steals Dave’s Truck

I learned to hate Leno from the moment he took over the Tonight Show because I was told Carson wanted Dave to take over. And when you watch moments like this, you can see the affection Johnny had for his protege. This is my favorite scene between the two, because Johnny is getting one over Dave for a change. You can hear the discomfort in Letterman’s voice as he realizes Carson has set up an elaborate prank around his beat up truck, and as it slowly unfolds, you can hear Dave get more and more uncomfortable. It ends with a great pay off, and further reminds you what a middling choice Jay Leno really was.

2. Jerry Lawler slaps Andy Kaufman

Of course this list would have a wrestling entry, but this really is one of the most shocking moments in TV history. Andy Kaufman is a god of absurd comedy, destroying all expectations of what’s funny, going from a sitcom star and comedian to a man who wrestles women and insults the people of Tennessee. This appearance was just one part of Kaufman’s feud with Jerry Lawler, but this was when wrestling wasn’t as fake as it is now, and Dave wasn’t in on the joke. The tense exchanges, Lawler slapping Andy, the swearing, it’s all too much for Letterman. It makes you wish The Rock and John Cena would show up and beat each other up on Dave’s desk today, but it just wouldn’t have the same zazz.

1. Norm Macdonald Says Goodbye

To be honest, this possibly won’t be remembered as the best ever in a few years, but it’s fresh enough right now to feel that way. I didn’t expect so many emotions during this clip because Norm MacDonald, while being a great comedian, is known for a dry delivery that keeps his feelings at a distance. Also, he played Dave in one of the meaner parodies of the show I’d ever seen:

And yet, with the end approaching, Norm gives one final, heartfelt standup performance that concludes with a tribute to Letterman that he has trouble completing.

Norm is tearful saying goodbye to a man he respects and admires, knowing that this really is the last time he’ll be able to perform on Late Show for Dave. It’s like a grieving son realizing he’s saying goodbye to his father, and it’s all hitting him at once. Honestly, that’s a bit of how I feel saying goodbye to Letterman too. Through heart surgeries and sex scandals, it just felt like he’d always be on TV, whether you watched him or not. And when you finally realize that such an institution is ending, it can fill you with emotions when you least expect it. Moments like that hit all the harder because you never see them coming.

7 thoughts on “The Top 10 Times David Letterman Got Too Real

  1. Never was a big fan of Madonna. But I just went down a Youtube rabbit hole of her appearances on Letterman after this article.

  2. I saw Cher on her last tour and she sang I got you babe with a projection of Sonny. It would be real corny if it wasn’t so beautiful.

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