David Letterman's 20 Most Controversial Interviews

1994: Madonna was a real bad girl.Bad.This remains one of the most famous episodes of all time. Madonna dropped the F-bomb 14 times and used other provocative words (double meanings, etc.) and acted unseemly for network TV. She did not return until 2000, but this night stays in TV infamy."Late Show"Madonna dropped the F-bomb 14 times and used provocative words (double meanings, etc.) and acted unseemly for network TV. She did not return until 2000, but this night lives in TV infamy.

1995: Finding out it was Letterman's birthday, Barrymore gave him a special present and flashed the host. Happy birthday.

2013: Lindsay Lohan became a popular punching bag for Letterman for years. Finally, Dave questioned her rehab stint, making the actress uncomfortable because it went off script.

1986: Cher let Letterman have it. She called him one of George Carlin's Seven Dirty Words, so be warned.

1982: One original controversial performance.Comedian Andy Kaufman.and pro wrestler Jerry "The King" Lawler guested on "Late Night" and fought. However, the stunt fooled everyone, including the host, because it promoted their upcoming wrestling match.

In 2006, shortly after the comedian known as Kramer on "Seinfeld" made a racist rant on a Los Angeles show, he appeared on "Late Show" via satellite to apologize for his actions; people remained upset.

1997: Fawcett was not the first person to sit next to Dave's desk, nor the last. But her odd interview made news then. Check the highlights above.

2009: After news broke about Letterman's infidelity, Rock appeared on the show and made fun of the host's personal problems.

1988: The "American Splendor" creator and the "Late Night" host clashed before. Things peaked on this show; bookers signed up Pekar to stir things up. The result? Late-night fireworks.

1987: Before Phoenix, there was Crispin Glover. The host and likely the audience did not know Glover acted out a part from his upcoming movie.River's Edge.. What happened mirrored Andy Kaufman's stunt with Jerry Lawler years earlier. After strange behavior, Letterman cut to the Top 10.

2009: Who forgets Joaquin Phoenix's stunt? No one knew then, including Letterman, that this was a gag for Phoenix's mockumentary.I'm Still Here.. His weird, rambling appearance still puzzles people, even though the actor explained himself the next time he was on the show.

2007: After Hilton was arrested, she appeared on "Late Show." She walked into a barrage of questions she likely did not prepare for. Letterman asked seconds later, "How much did you like jail?" Ouch.

In 2008, McCain skipped a scheduled appearance on Letterman during the presidential campaign. Letterman clearly was unhappy.

In 2004, Courtney Love channeled Barrymore, showing off her body to Letterman.

In 2006, Howard Stern dressed in drag to promote his move to Sirius, appearing on the show for a broader audience. Stern left CBS Radio just before this, leading to a lawsuit between the company and the DJ after the performance.

In 2011, Dave did not ask for ketchup on his paper after Lady Gaga, who disliked the line of questions.

In 2006, Letterman disliked seeing Sacha Baron Cohen as Borat instead of himself. The result was not 'very nice!'

In 2008, Kristen Stewart appeared awkward and testy, leaving Dave with little to do.

In 2014, the two discussed Beyonce. They have gone back and forth over the years.

In 2006, the show needed only two words for this incident: fire extinguisher. Richard Simmons had appeared on the show for years.