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David Letterman's 20 Most Controversial Interviews

Updated June 14, 2019 1.7k votes 371 voters 35.0k views20 items

List RulesUpvote the most controversial interviews of David Letterman's career.

Since he became a late-night TV show host, David Letterman has done his fair share of interviews. But here, we're going to look at the ones the garnered the most attention, for better or worse. Letterman is very good at getting a rise out of his guests...or unsuspectingly ambushing them with a line of questioning that would catch them off-guard. Better yet, the most talked about interviews happened when no one saw them coming, like in the cases of Andy Kaufman/Jerry Lawler, Crispin Glover and Joaquin Phoenix. During these times, Dave wasn't in on the joke, and it led to some uncomfortable times and unintentional comedy.

These are some of the most controversial, albeit infamous, interviews of David Letterman's career. You may find some of these names familiar, others you may not, but no matter what the case, you should have a few laughs, a few cries and a few cringes. Enjoy!
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    1987: Before there was Phoenix, there was Crispin Glover. Unbeknownst to the host and likely anyone else in the audience, Glover went in character from his upcoming movie (at the time) River's Edge. What happened was similar to Andy Kaufman's stunt with Jerry Lawler a few years prior. After some strange behavior, Letterman cut to the Top 10. 
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      2008: In the heat of the presidential campaign, McCain was a no-show during a booked appearance on Letterman. Needless to say, the host wasn't thrilled.
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        2006: Shortly after the comedian best known as Kramer on "Seinfeld" went on a racist rant at a show in Los Angeles, he appeared via satellite on the "Late Show" to apologize for his actions, which people were still upset about. 
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          1988: The "American Splendor" creator and the "Late Night" host had butted heads in the past, but things came to a head on this particular show, where it seems like the show's bookers signed up Pekar just to stir the pot. The result? Late-night fireworks.
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