David Letterman’s 5 Most Confrontational Interviews

Crispin Glover Kick on Late Night With David Letterman

Glover: “I can kick!”

An era ends tonight with David Letterman’s final episode of The Late Show. Letterman is an institution on TV of course, and he’s also about as old as we are, in a way. Heavy Metal‘s first issue came out in 1977; Letterman at that time was a nationally-known standup comedian, and in 1978 proved himself a viable talk show host as Johnny Carson’s regular fill-in on The Tonight Show. It took NBC another couple years to figure out how to use Dave’s talents, but eventually he got his signature show, Late Night With David Letterman. Letterman back in the day brought an irreverence and sense of risk to late-night programming that we—and we suspect, our readers—could really dig. You just didn’t know what would happen, and there were plenty of “what did I just see?” moments as well.

Letterman’s a born comedian, but not necessarily a born interviewer. His attempts to manage ornery or creepy guests are some of the best moments in talk show history. Here are five unforgettable encounters (and we apologize for the poor quality of some of these videos; many were taken from VHS tapes):

1. 1987: Crispin Glover nearly kicks Dave in the head

…Crispin Glover returns, three weeks later, seems like a totally different (still weird) person

2. 1994: Madonna spews profanity and cracks jokes about Charles Barkley’s penis

…Part 2 of the Madonna interview

3. 2009: Joaquin Phoenix, former actor and aspiring hip hop star, seems completely out of it

4. 1986: Cher calls Dave an “asshole”

5. 1987: Harvey Pekar being Harvey Pekar

This is typical of Pekar, the late writer of American Splendor comics and graphic novels—just pure curmudgeonry:

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Published on: May 20, 2015

Filled Under: News, TV

Views: 27213

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One Response to David Letterman’s 5 Most Confrontational Interviews

  1. Steven dr says:

    Harvey may not be the most likable person but his courage to state what were the questionable practices of GE at the time is commendable. It is also attention grabbing and so the question is.. was it to grab attention to him or to shine light on the dark history of General Electric? both? perhaps only Harvey can say or wouldn’t say if he were still with us.

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