How many shocking moments from David Letterman's tenure on late-night television can you think of? And are there any other celebrity interviews that didn't happen on Letterman that you're surprised ended up airing? Let us know down in the comments.

▬Contents of this video▬
00:00 - Intro
00:48 - Bill O'Reilly
01:37 - Madonna
02:16 - Paris Hilton
03:33 - Lindsay Lohan
04:20 - Janet Jackson
05:26 - Jennifer Aniston
06:12 - Gwen Stefani
06:38 - Crispin Glover
07:05 - Drew Barrymore
07:33 - Farrah Fawcett
08:17 - Outro

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David Letterman started his career as a late-night talk show host with The David Letterman Show on NBC which ran from June 23, 1980 to October 24, 1980. He later made his return to late-night television with The Late Show on CBS which debuted on August 30, 1993. After 33 years and 4,261 episodes, Letterman filmed his last episode of the program on May 20, 2015.

The Ed Sullivan Theater, the historic locale where the show was filmed for decades, was often the setting for some of the most controversial, scandalous, and talked-about moments in television history.

From Madonna dropping the F-Bomb 14 times to Dave sucking on the hair of Jennifer Aniston, there was never a dull moment on the set of Letterman's talk shows. Many of these moments involved unusually tense interviews with stars who didn't seem to be bothered by giving Dave a hard time, while others involved Dave acting like a bully. In this video, we'll be looking back at several controversial interviews with David Letterman that probably shouldn't have been aired on TV.

David Letterman's Most Controversial Interviews That Shouldn't Have Aired on TV