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David Letterman's 20 Most Controversial Interviews

Updated June 14, 2019 1.7k votes 372 voters 35.2k 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!