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Letterman kept talking about Jennifer Aniston's legs in creepy interview: "You can only wear..."

Jennifer Aniston's legs get more attention than she bargained for on David Letterman’s show and it's uncomfortable as hell

Jennifer Aniston did not exactly have a gala time during her appearance on 'Late Show with David Letterman' and was taken aback when the host David Letterman passed an awkward compliment. Though she handled the situation like a seasoned professional, the interview has since resurfaced, sparking debate over how Letterman made her uncomfortable.

During an appearance on 'Late Show with David Letterman', the 'Friends' star was bombarded with personal questions; however, what raised eyebrows was Letterman complimenting Aniston's legs, as per The Things. Letterman immediately fixated on Aniston's legs and said, "Wow. You look great. That's a tremendous outfit, and the reason that's a tremendous outfit is because you have tremendous legs. Fantastic legs. You can only wear that if you have well-shaped, lovely, lengthy legs." Aniston, maintaining her composure, downplayed the situation by explaining she wore shorts simply because "it was hot outside at the time." Letterman did not stop there as he continued the compliment, saying, "Your legs, you got something there."

Letterman, unfortunately, had more than one interaction that left Aniston feeling uneasy, as another appearance was even more uncomfortable than the last. The interview began like any other, but things took a creepy turn when Aniston shared a 1998 anecdote about encountering fans in her gym’s steam room, as per Image. Letterman then interjected with unsettling questions, asking, "How many naked women were there?" and whether they were "sweaty." 

The exchange shifted the tone of the conversation, making for an uncomfortable moment, which further took a turn for the worse when Letterman moved behind Aniston, telling her, "Forgive me if this is rude, I just want to try one thing," before unexpectedly putting a strand of her hair in his mouth. As she shouted, "What are you doing?!" he sucked on it before slowly pulling away. Though Aniston laughed along, her discomfort was clear as she accepted a tissue to dry his saliva from her hair.

Unfortunately, Aniston isn’t the only female celebrity who faced Letterman's embarrassing antics; he also crossed paths with Angelina Jolie in an awkward moment. The interview started on a rocky note when Letterman asked Jolie if she cooks or bakes, to which she sarcastically replied, "No, I'm not a good woman, Dave." The awkwardness continued when Letterman commented on her scent, saying, "You smell great, you smell nice, that’s a lovely fragrance, I appreciate that."

Jolie responded uncomfortably, "Anything I can do," as per The Things. The conversation briefly regained focus until Letterman asked if she was married, prompting Jolie to pause before revealing she was "in the process of getting a divorce" from Jonny Lee Miller. The awkwardness continued when the topic of Jolie’s tattoos came up. She made it clear she "wasn't going to climb on Dave's desk" to show them off, making a subtle jab at his questioning. The interview eventually shifted back to discussing her latest film, but it remained brief.