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

David Letterman began his tenure as a late-night talk show host with The David Letterman Show on NBC which ran from June 23, 1980, to October 24, 1980. Over a decade later he returned back to the world of 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.

As with many stars who have had extensively long careers in show business, Dave’s was filled with just as many high points as low ones. The Ed Sullivan Theater, the historic locale where the show films for so many years, is more than Letterman likes, the setting for some of the most controversial, scandalous, and talked about moments in television history.

Many of these moments involves unusually tense interviews with stars who didn’t bother by giving Dave a hard time, while others seem to be tied to the now-74 year host having particularly a bad day. Often Dave made himself look like a bully and occasionally he seemed more like someone’s creepy uncle than a veteran television star.

In this video, we’ll be looking back at several controversial interviews from David Letterman’s glory years that probably shouldn’t have been aired on TV.

Most Controversial Interview #1 Bill O’Reilly

On January 3, 2006, Letterman invited conservative media personality, Bill O’Reilly on to his program. Quickly the interview devolved into a pretty heated argument over the War in Iraq. The interview eventually became so tense that Letterman couldn’t seem to prevent himself from taking a few low-blow jabs at his guest.

At one point Dave accused O’Reilly of ‘putting words’ in his mouth just like how he ‘put artificial facts’ in his head. Letterman followed that up by quipping that 60% percent of what Bill was saying was probably ‘crap’.

Fortunately, the two eventually managed to let bygones be bygones and set aside their differences. Even though they seemingly were able to patch things up, O’Reilly eventually made another appearance on The Late Show in March 2015. Not surprisingly, things got pretty dicey once again.

Most Controversial Interview #2 Madonna

Arguably, the single-most controversial interview that Letterman ever conducted was his March 31, 1994 interview with Madonna. Right off the bat, things got off to a pretty rocky start. As soon as Madonna sat down, Letterman joked that his guest had ‘slept with some of the biggest names’ in show business.

Madonna appears to be visually uncomfortable and upset after that remark, but even Letterman wasn’t prepared for what was about to happen. During an awkward exchange that included several passive-aggressive insults and innuendos, Madonna managed to say the F-word a grand total of 14 times. Because of that, the episode is to this day one of the most censored late-night television episodes in history.

Most Controversial Interview #3 Paris Hilton

In 2007, shortly after the Hotel heiress’s arrest and serving time for violating her probation after she receives an alcohol-related reckless driving charge, she made an appearance on the Late Show. At that point, she hadn’t done an interview in months because she simply didn’t want to talk about her legal troubles or jail stint. Letterman’s team repeatedly contacted her PR people to try and get her to come on the show. After several emphatic nos, eventually, Hilton agreed to go on the show to promote her fragrance line.

Her team made an agreement with Letterman that discussion of her jail sentence would be strictly off-limits. Despite these terms, as soon as her interview with Letterman began, he immediately pushed her to talk about the subject.

For several uncomfortable minutes, Hilton faces a barrage of questions that she’s not ready to answer. It almost seemed as if Dave had made it his mission to humiliate her because right from the get-go, he asked her how much she liked her time in jail. He then grilled her for several minutes about what the food was like and what she had learned from the experience.

Hilton eventually responded to his onslaught of personal questions by saying that she had ‘moved on’ and didn’t want to discuss it, but Letterman continued to press the issue. Hilton looked distressed and embarrassed but Letterman didn’t seem to care in the slightest.

After leaving the stage, Paris was reportedly in tears, crying and shaking. Fortunately, her sister Nicky was there to comfort and support her.

Most Controversial Interview #4 Lindsay Lohan

The since-retired ‘Parent Trap’ actress stopped by the Ed Sullivan Theater for a chat with Dave in 2013 to promote her latest flick, ‘Scary Movie 5’, but similarly to how he seemed obsessed with Paris Hilton’s troubles, Dave seemed far less interested in talking about her professional career and instead hit her with a steady stream of questions about her forthcoming admittance to a drug rehabilitation facility. At one point Lohan stated that she had expected Letterman to have played nice and that they hadn’t talked about any of what he was quizzing her about in the pre-interview.

Despite the fact that Lohan was obviously uncomfortable and had stated that her healing process wasn’t a ‘joking matter’, Letterman continued to berate her with questions and jokes about rehab and her previous struggles with addiction. By the end of the interview, Lohan was in tears.

Janet Jackson

After the infamous ‘wardrobe malfunction’ at 2004’s Super Bowl Halftime Show, Janet Jackson and Justin Timberlake are subjects to a mountain of scrutiny for what many suspected to be an intentional act of voyeurism.

Shortly after the big game and the ensuing media fiasco, Jackson appeared as a guest on the Late Show. Letterman proceeded to spend the brunt of the interview trying to get Jackson to divulge details about the controversial nip-slip.

As soon as he started prodding her, Jackson told Letterman that she didn’t want to ‘relive’ any of that fateful evening. Letterman then flat-out ignored her requests to change the subject and questioned her repeatedly about whether the moment had been pre-planned as some kind of publicity stunt. Jackson denied this allegation several times while remaining composed.

Later in the interview, Jackson say that there are more important things in the world to be focusing on. Shifting away from that topic, Letterman then asked Jackson about her brother Michael Jackson who had been arrested on charges of child molestation months prior. Jackson shut the questioning down immediately saying that she would not discuss the matter. Only at the last few seconds of the interview did Letterman ask her about her latest album ‘Damita Jo’.

Jennifer Aniston

Dave’s interview with the ‘Friends’ actress began fairly normal, despite asking her if she was naked during an anecdotal story she told about meeting her fans in a steam room.

Later in the interview, he interrupted her to ask if he could ‘try one thing’. Letterman then shuffled his chair up close to the actress, placing his hand firmly on her shoulder, and put a strand of her hair into his mouth.

She reacted as expected – by screaming and asking him what he was doing. Aniston appeared extremely disturbed and confused as Dave continued to suck on the piece of hair until it fell out of his mouth. He then handed Jennifer a tissue to dry her slobber-soaked hair.

Dave then apologized, albeit insincerely, and said that it must have been something to do with the ‘steam room’ story.

Letterman then said that she screamed like she was ‘traumatized’. Aniston responded by saying that she had been.

Can you imagine if a host were to try and pull this kind of move today? Hopefully, he’s learned a thing or two about consent in the years that have transpired since that disturbing encounter.

Gwen Stefani

During her five-minute interview with Letterman, Stefani discussed her new album, clothing line, and marriage to Gavin Rossdale. Between asking her various questions about her various projects, Letterman threw in compliment after compliment about the No Doubt singer’s looks. Later, he said that she smelled great as well. Towards the end of the interview, while discussing her latest record, Letterman made one last seemingly unwanted remark by telling Gwen that she had ‘tremendous legs’.

Crispin Glover

On July 28, 1987, Glover showed up to do Letterman to promote his latest film Rivers Edge. Unbeknownst to Dave or likely anyone, Crispin decided to do the interview in character. He wore a wig and platform shoes and behaved erratically and awkwardly throughout the incredibly uncomfortable-looking chat. At one point he got up and almost kicked Letterman in the face, causing the host to shut the interview down and walk off the set.

Drew Barrymore

In what has gone in history as one of the most memorable late-night moments of all time, Drew Barrymore, after finding out that it was Dave’s 48th birthday, decided to give her host a very special spontaneous Birthday present. Barrymore appeared on the Late Show previously, but this time around in January of 1995, after telling a story about dancing at a nude performance art show in New York City, Drew hopped on top of Dave’s desk, danced, and quickly flashed him.

Farrah Fawcett

The Charlie’s Angel accused Letterman of making fun of her – which of course he was – during a very painful to watch interview on Letterman in 1997. For nearly 20 minutes, Fawcett told several long, nonsensical, and at times creepy stories that seemed like would never end. She was there to promote a Playboy issue that she was on the cover of and a new pay-per-view special that she had been a part of, but it seemed very likely that she was on something at the time.

Farrah seemed confused, disoriented, and downright incoherent throughout the segment. At one point, she looked back at the set’s backdrop and said ‘wow’ as if she thought that it was actually New York City that she was looking at. From start to finish, the interview was like a train wreck happening in slow motion, but even so, Fawcett seemed to be having a great time.

That about wraps up this video. Can you think of any other moments from David Letterman’s tenure on late-night television that you found particularly shocking? And are there any other celebrity interviews that didn’t happen on Letterman that you’re surprised ended up airing? Let us know in the comments.

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