David Letterman’s old interviews with famous women are going viral for their inappropriate nature. Here are the most uncomfortable ones. – Yahoo News

Actress Lindsay Lohan appeared on "Late Show With David Letterman" in 2013. CBS Photo Archive/Getty Images

Several of David Letterman's old late-night interviews have resurfaced.

Many people have criticized his past treatment toward the women that joined him as on-air guests.

Insider rounded up 11 of the former talk-show host's interviews that haven't aged well.

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David Letterman interviewed some of the biggest names in entertainment during his 33 years in the late-night circuit.

The 73-year-old, who hosted NBC's "Late Night With David Letterman" before CBS' "Late Show With David Letterman," was known for pushing boundaries and asking those "big names" startlingly direct questions.

But after several of his old interviews with famous women like Lindsay Lohan, Jennifer Aniston, and Paris Hilton resurfaced online in 2021, some people are reconsidering their opinion of the long-time talk-show host.

Many are saying that he crossed lines.

The outcry against Letterman's past behavior stemmed from the February release of The New York Times documentary "Framing Britney Spears," which examines the media's misogynistic treatment towards women.

And Letterman is just one of many prominent figures facing scrutiny in the aftermath of the documentary.

Keep reading to see 11 of his interviews that haven't aged well.

The "Parent Trap" actress appeared on "Late Show" in 2013 to promote "Scary Movie 5," but Letterman seemed far less interested in her professional projects than on her forthcoming return to rehab.

Right off the bat, the host told Lohan that she looked "remarkably well" before launching into invasive questions about whether or not she steals things and manages her money responsibly.

His go-to punchline, though? Her plans to check into rehab.

The actress answered his questions about when she was going to rehab and how long she planned to be there. Eventually, Lohan told the audience that she and Letterman "didn't discuss this in the pre-interview" and asked the host to "stay on the positive."

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Despite Lohan's obvious discomfort and statement that her healing process is "not a joking matter," Letterman returned to the topic later, leaving Lohan in tears.

After Justin Timberlake exposed Jackson's breast during the 2004 Super Bowl halftime show, the moment received an explosive amount of media attention.

So when Jackson appeared on "Late Show" shortly after, Letterman spent the majority of the interview prodding her for behind-the-scenes details.

"I don't want to relive any of that," the guest said right away.

Letterman ignored her request and repeatedly asked if the onstage moment was a preplanned stunt, a suggestion that Jackson denied multiple times.

She remained composed, telling Letterman to ask her about something else as it was "very embarrassing" to have her breast shown on live television.

"There are more important things to focus on in this world," she told him.

When they pivoted from the halftime show, Letterman dove into her dating life and asked about her brother, late performer Michael Jackson. Months earlier, the "Billy Jean" singer had been arrested on charges of child molestation, which he denied. She refused to speak on the matter.

Only at the very end of the interview did Letterman ask Jaskson about her CD "Damita Jo."

As he did with many of his other guests, Letterman welcomed Alba to the stage by telling her she looked "fantastic" and smelled "even better."

The actress, who was on the show to promote the movie "Honey," said that filming one particular dance scene in a "tiny, little outfit" made her uncomfortable.

Letterman followed up: "How tiny was it? Where was it tiny?"

As the actress was describing her role as a "coquette" in "A Month by the Lake" during a 1995 interview on "Late Show," Letterman stopped her to talk about Thurman's personal life.

She continued discussing the project until Letterman said he's "not talking about the film now" and asked if she'd ever dated an older man. He then asked if she'd been with a 30-year-old, a 35-year-old, or a 48-year-old - his age at the time of the interview.

Letterman then asked if she'd been married before. After she replied that she had, he asked if it was "traumatic" before saying he would stop asking her about such a "miserable part" of her life.

"God, your ears are just perfect," he then told the actress, who replied, "Thank you."

As Letterman circled back to "A Month by the Lake" at the end of the interview, he said, "It's a lovely, lovely piece of work, as are you."

The interview between Letterman and the "Friends" actress started out seemingly normal, despite the host's request to know if Aniston was "naked" during her anecdote about meeting fans in a steam room.

He later paused their conversation and said: "Forgive me if this is rude. I just want to try one thing."

Letterman then scooted his chair behind the actress, placed his hand on her shoulder, and put a piece of her hair in his mouth.

She squealed and asked what he was doing, appearing confused as Letterman sucked the strand until it dropped from his mouth. He then handed Aniston a napkin to dry her hair.

"I'm sorry," he said, adding, "Something to do with the steam room."

Letterman joked that they'd edit out the moment, and Aniston replied, "That was something that I'll never forget."

When the actress seemed shaken in the moments that followed the interaction, Letterman told her she seemed "traumatized."

She responded, "I am."

Between her marriage to Gavin Rossdale, her new music, and her clothing line, Stefani had plenty to discuss with Letterman when she visited his show.

However, the host seemed to pivot from topic to topic by making a comment about Stefani's appearance.

"You look tremendous," he said, later adding, "You smell great too."

When she explained the process that went into her latest record, Letterman responded, "You have tremendous legs."

The pop star stirred up controversy during her 1994 appearance on "Late Show," during which she said "f---" 14 times and made a series of expletive jokes on-air.

Letterman wasn't blameless in the situation, however.

As soon as Madonna joined him onstage, he urged her to kiss a man in the audience. When she refused, he continued to vocalize the suggestion.

"Why are you so obsessed with my sex life?" she asked him, adding, "You are a sick f---."

The singer visited "Late Show" in 2001 to promote a special called "Home for the Holidays." Midway through the interview, Letterman tried to refocus the interview on Carey herself.

"What do you do when you want to have fun and stuff? Because you look like a girl who likes to have fun," he said.

When she responded by saying she enjoys swimming, the audience erupted in laughter.

"I do like to have fun, Dave," she followed up.

Carey later shared that she had plans to go skiing over the holidays. She told Letterman that she's not very skilled but enjoys the sport because of her fashionable snow outfits.

"I like the outfit you got here now," he said, looking at her dress. He added, "You don't ski in that, do you? Whoa, Nelly."

The country star appeared on "Late Night" in 1987 to promote Dollywood, her theme park in Tennessee.

As soon as she walked out to the stage, Letterman told her that they "look good together." He added that she smelled "great" shortly after she sat down.

They began by chatting about the amusement park before the host jumped in to say: "Please marry me."

Parton joked that she'd "consider it," even though she'd been married to her husband Carl Dean for over 20 years at the time of the interview.

During Hilton's visit to "Late Show" in 2007, Letterman spent the majority of the interview asking about her time spent in jail.

Months earlier, Hilton was sentenced to 45 days in jail after a judge ruled she violated her probation for a previous traffic offense. Her sentence was ultimately reduced to 23 days.

On her podcast, "This Is Paris," she said Letterman agreed not to talk about her sentence on the show and focus on the fragrance she was promoting.

Moments after she saw down opposite the host, he asked: "How'd you like being in jail?"

Letterman pressed Hilton to give him answers to his questions about jail for the rest of the interview, even when she said she didn't "really want to talk about it."

"It was like he was purposely trying to humiliate me. During commercial breaks, I would look at him like, 'Please stop doing this. You promised me you wouldn't talk about this. That's the only reason I came on the show. Please don't bring it up again,'" she said.

Hilton said she left the stage "crying" after the interview, adding the Letterman later apologized to her. She visited the show again years later, and Letterman told her he was sorry for his past behavior once again.

When the actress appeared on "Late Show" to talk about her role in the film "Hancock," Letterman greeted her with a string of compliments about her looks.

"Wow. Boy oh boy. You look fantastic, beautiful, just gorgeous, a vision. Oh my God," he said as she sat down, later adding, "Nice going."

Theron then mentioned that her birthday was approaching and joked that Letterman should send her a gift. He told her, "I'm sending you something right now."

"I didn't want that," she told the host, who replied, "I know. Nobody does."

Their conversation then moved on to Theron's appreciation for the outdoors, and the actress mentioned that she's OK going without a shower during trips. When Letterman and Theron moved on to discuss "Hancock," the host circled back to her previous comment.

"What's the longest you've gone without showering?" he asked her out of the blue.

Paul, the band member, cut in to say: "David! David! Behave."

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David Letterman's old interviews with famous women are going viral for their inappropriate nature. Here are the most uncomfortable ones. - Yahoo News

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