interviews David Letterman's 20 Most Controversial Interviews  

Daniel Kohn
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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!

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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: 42

Birthplace: Río Piedras, Puerto Rico, Puerto Rico

Profession: Television producer, Musician, Film Producer, Actor, Music video director, + more

Credits: Gladiator, Walk the Line, The Master, Her

Also Ranked

#44 on The Best Actors Working Today

#22 on The Best Living American Actors

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

#72 on The Best Actors in Film History

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24 10

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: 42

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

Profession: Television producer, Film Producer, Model, Screenwriter, Author, + more

Credits: Donnie Darko, Charlie's Angels, Scream, My Date with Drew

Also Ranked

#97 on The Best American Actresses Working Today

#99 on The Best Actresses in Film History

#81 on The Most Trustworthy Celebrities in the World

#96 on The Best Living American Actresses

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22 9

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, New York, United States of America

Profession: Wrestler, Comedian, Screenwriter, Actor, Writer, + more

Credits: Taxi, Heartbeeps, I'm from Hollywood, My Breakfast with Blassie

Also Ranked

#87 on The Funniest People of All Time

#48 on The Funniest Stand Up Comedians of All Time

#26 on The Most Original Comedians

#10 on The Best Male Stand Up Comedians of the '70s

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29 16

Chris Rock


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2009: After news broke of Letterman's infidelity, Rock came on the show and poked fun at the host's personal troubles. 

Age: 52

Birthplace: Andrews, South Carolina, United States of America

Profession: Comedian, Television producer, Film Producer, Screenwriter, Actor, + more

Credits: Chris Rock: Bigger & Blacker, Madagascar, Head of State, The Oscars

Also Ranked

#14 on The Funniest People of All Time

#18 on The Best SNL Cast Members of All Time

#94 on Celebrities Who Should Run for President

#7 on The Funniest Stand Up Comedians of All Time

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