5 Most Memorable David Letterman Interviews

Joaquin Phoenix, David LettermanCBS

In honor of David Letterman‘s 20 year reign as late night talk show host on The Late Show with David Lettermanwe’re looking back at some of his most memorable interviews. Below are five of the most entertaining, which remind us why he’s remained a constant presence in our lives, and why we’re going to miss him when he goes. Nobody else can play caustic and abrasive as charmingly as Dave.

5. Joaquin Phoenix, 2009

At the time of this debacle, none of us knew that Phoenix was commenting on the absurdity of stardom with his surreal appearance on Letterman in 2009. We all just thought he was losing his mind. Despite it being a joke, the interview caused a sensation and Letterman’s reaction is nothing short of hilarious. 

4. Drew Barrymore, 1995

For Letterman’s birthday present, actress Drew Barrymore flashed him in front of the live audience. There’s debate about whether or not this moment was spontaneous or scripted, but it hardly matters. So often these celebrity interviews are boring and monotonous, and Barrymore spiced it up with a moment we’re never going to forget. 

3. Madonna, 1994

In 1994, the Queen of Pop caused controversy as usual when she cursed and talked about sex. At the time, half of the audience was annoyed with Madonna and the other half admired her courage to defy the rules. Now we’re all grateful for this rare moment of off-kilter insanity. 

2. Harmony Korine, 1995

Provocateur Harmony Korine deliberately annoyed Letterman in this uncomfortable interview that reminded viewers of the importance of knowing something about a guest before inviting them on the program. What else is to be expected from the guy who made Gummo

1. Kristen Stewart, 2008

Kristen Stewart is an awkward celebrity in general, and her interactions with Letterman during this interview are painful to watch. You can tell she doesn’t want to be there, and Letterman doesn’t make it easier by asking her ridiculous questions and then mocking her answers in order to elicit a laugh from the audience. This is late night television at its finest.