David Letterman Kept Hitting On Uma Thurman During An Extremely Uncomfortable Interview

Summary

• David Letterman's conduct upset some guests, including Uma Thurman.
• Thurman felt uncomfortable when Letterman asked personal questions about her relationships with older men.
• There is no evidence to suggest that Letterman had an obsession with Thurman, but his failed Uma, Oprah joke at the Oscars haunted him for years.

For anyone who gets the opportunity to become a talk show host, it would make sense to examine David Letterman's career. After all, Letterman became a legendary figure who is so rich that he can afford to lead a truly incredible lifestyle.

However, it would be a mistake for anyone to think that Letterman's career was unproblematic. In reality, Letterman's conduct upset some of his guests, which even resulted in some stars walking off his show. A perfect example of the sort of thing that Letterman did wrong was his incredibly uncomfortable interview with Uma Thurman.

David Letterman's Inappropriate Flirting Made Uma Thurman Uncomfortable

When celebrities appear on talk shows, they should be able to feel comfortable as they promote whatever project they are there to discuss. Unfortunately for Uma Thurman, however, it was very obvious that David Letterman once made her feel uncomfortable.

In 1995, Thurman starred in a mostly forgotten romantic comedy titled A Month by the Lake alongside an actor named Edward Fox. In A Month by the Lake, Thurman's character flirted with Fox's character.

When were Uma Thurman and Edward Fox born, according to Britannica and Empire Online?

The reason why Thurman's character flirting with Fox's character in the film was noteworthy is the large age difference between the two actors. After all, Thurman was almost exactly 33 years younger than Fox was in real life. That age difference played a significant role in A Month by the Lake's plot.

When Thurman was promoting A Month by the Lake, she made an appearance on Late Show with David Letterman. During the resulting interview, it didn't take too long for David Letterman to bring up his interest in the prospect of Thurman getting involved with an older man.

Just like Edward Fox was before his passing, David Letterman is significantly older than Uma Thurman. In Letterman's case, he is almost exactly 23 years older than Thurman is.

As a result of their age difference, it seemed like David Letterman took a special interest in the character Thurman portrayed in A Month by the Lake. However, during their interview, it quickly became clear that Letterman wasn't overly interested in talking about the film with Thurman. Instead, Letterman wanted to talk about Thurman's relationships with older men like him.

As they were discussing A Month by the Lake, Letterman asked Thurman if her character in the film marries the older man. Letterman used that as his opening to ask Thurman about her private life.

First off, Letterman asked Thurman, "Have you ever been married yourself?" By the time of the 1995 interview, Thurman had gotten married to Gary Oldman only for them to get divorced not long after.

Clearly, Thurman didn't have any interest in discussing her former marriage, as she continued to talk as if Letterman was asking about her film. Undeterred, Letterman clarified that he was asking about Thurman's private life. "Okay. I'm not talking about the film now. We'll talk more about you."

At that moment, Thurman seemed to feel like she had no choice but to acknowledge what Letterman was talking about. However, she still didn't want to answer Letterman's question, and she playfully communicated that to the talk show host. "Oh no. I'm just trying to see if we get past that."

Thankfully for Thurman, Letterman gave up on asking her if she'd been married in the past. However, that didn't mean that Letterman changed the subject to something the actor was more comfortable with.

Who celebrities has Uma Thurman been involved with according to Whos Dated Who?

• Don Johnson
• Married to Gary Oldman between 1990 and 1992
• Richard Gere
• John Cusack
• Robert De Niro
• Timothy Hutton
• Married to Ethan Hawke between 1986 and 2004
• Rumored to have dated Quentin Tarantino

Letterman followed up his original query with a series of questions about Thurman dating older men. Keep in mind that Thurman's ex-husband, Gary Oldman, was roughly 12 years older than her.

"Would you, yourself, date an older man? What's the oldest man you've ever gone out with? You're 25, ever been out with a guy 30?"

When Thurman confirmed that she'd been involved with a man who was five years old, Letterman kept pushing. First off, Letterman asked Thurman if she'd been involved with someone who was 35 or older, and she again confirmed she had. Then, Letterman asked Thurman about the exact age he was at the time; 48.

After Thurman stated that she'd never dated a man that age or older, Letterman looked at the camera with a devilish grin on his face. Letterman then went on to pledge he would change the subject but not before he commented on Thurman's looks.

"I know now that I'm going to stop asking you about this miserable part of your life. But god, your ears are just perfect."

After Thurman thanked Letterman as she sounded uncomfortable, she was asked about her movie's release. When Thurman commented that the number of theaters the movie was in was "growing a little bit more", Letterman erupted in laughter. Letterman then complimented Thurman again. "Well, it's a lovely, lovely piece of work. As are you."

Was David Letterman Obsessed With Uma Thurman In 1995?

When Uma Thurman appeared on Late Show with David Letterman to promote A Month by the Lake in 1995, things were already complicated. The reason for that is, earlier in the year, Thurman had been linked in the media to Letterman because of a joke he made.

In March 1995, Letterman hosted the 67th Academy Awards. During that ceremony, Letterman made one of the most memorable jokes of his career because it completely flopped.

Who has David Letterman been involved with according to Whos Dated Who?

• David Letterman began dating Regina Lasko in 1986
• David Letterman and Regina Lasko got engaged in 2001
• David Letterman and Regina Lasko have been married since 19th Mar 2009
• David Letterman and Stephanie Birkitt had an affair between 2001 and 2003
• David Letterman had a fling with Terri Garr in 1990
• David Letterman dated Bonnie Hunt

In the opening seconds of his Academy Awards monologue, Letterman walked over to one side of the stage and acknowledged Oprah Winfrey. Letterman then found Uma Thurman in the crowd and said her first name. Letterman then proceeded to repeat Winfrey and Thurman's first names, referencing how similar they were, and that was the joke.

Given the infamous Uma, Oprah joke and the way he hit on Thurman during their 1995 interview, it could be reasonable to suggest Letterman was fascinated by her. However, it seems almost certainly untrue that Letterman had any kind of obsession with Thurman.

That said, it would be reasonable to think that the failed Oscars joke haunted Letterman at least for some time. After all, Letterman has addressed how disastrous his Academy Award hosting gig was as recently as 2020, which was 25 years after that event. Letterman's discussion about that subject especially focused on the Uma, Oprah joke.