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David Letterman's 20 Most Controversial Interviews

Updated June 14, 2019 1.7k votes 369 voters 34.8k 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!
  • Paris Hilton
    Video: YouTube
    2007: After Hilton was arrested, she appeared on the "Late Show," where she blindly walked into an onslaught of questions that she probably wasn't prepared for. Within seconds of sitting down, Letterman asked, "How much did you like jail?" Ouch.
    • Age: 39
    • Birthplace: New York City, New York, United States of America
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  • Drew Barrymore
    Video: YouTube
    1995: Upon finding out it was Letterman's birthday, Barrymore decided to give him a special birthday present and flashed the host. Happy birthday indeed.
    • Age: 45
    • Birthplace: Los Angeles, Culver City, California, United States of America
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  • Madonna
    Video: YouTube
    1994: Remember when Madonna was a real bad girl? This remains one of the most famous "Late Show" episodes of all time. Madonna dropped the F-bomb 14 times and used a number of other provocative words (double meanings, etc.) and acted a bit unseemly for network TV. She didn't return again until 2000, but either way, it is a night that will live in TV infamy.
    • Age: 62
    • Birthplace: Bay City, Michigan, United States of America
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  • Andy Kaufman
    Video: YouTube
    1982: One of the original controversial performances, comedian Andy Kaufman and pro wrestler Jerry "The King" Lawler guested on "Late Night" and appeared to get into a fight. But alas, it ended up fooling everyone there, including the host, as it was a stunt to promote their upcoming wrestling match.
    • Age: Dec. at 35 (1949-1984)
    • Birthplace: New York City, USA, New York
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