Interviews David Letterman's 20 Most Controversial Interviews  

Daniel Kohn
512 votes 116 voters 26.6k views 20 items

List Rules Upvote 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!
1 36 VOTES

Joaquin Phoenix


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2009: Who could forget Joaquin Phoenix's stunt? Though no one knew it at the time, including Letterman, that this was part of a gag for Phoenix's mockumentary, I'm Still Here. His bizarre, rambling appearance is still a headscratcher, even though the actor explained himself the next time he was on the show. 

Age: 43

Birthplace: Río Piedras, Puerto Rico, Puerto Rico

Also Ranked

#44 on The Best (Male) Actors Working Today

#17 on The Greatest Actors Who Have Never Won an Oscar (for Acting)

#32 on The Greatest Former Child Stars

#22 on The Best Living American Actors

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Drew Barrymore


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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: 43

Birthplace: Culver City, Los Angeles, California, United States of America

Also Ranked

#54 on The Best Actresses Working Today

#84 on The Most Trustworthy Celebrities in the World

#85 on The Best Actresses in Film History

#1 on The Greatest Former Child Stars

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Andy Kaufman


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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: Died at 35 (1949-1984)

Birthplace: New York City, USA, New York

Also Ranked

#91 on The Funniest People of All Time

#48 on The Funniest Stand Up Comedians of All Time

#56 on The Greatest Entertainers of All Time

#24 on The Most Original Comedians

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Cher


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1986: Yikes! Cher really lets Letterman have it here. She calls him one of George Carlin's Seven DIrty Words, so consider yourself warned. 

Age: 71

Birthplace: El Centro, California, United States of America

Also Ranked

#89 on The Best Singers of All Time

#33 on The Best Female Vocalists Ever

#76 on The Best Current Female Singers

#33 on The Best Female Rock Singers

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