David Letterman was once hailed as the master of late-night television, known for his wit and charm. But looking back, it’s fair to say that not all of his interviews have stood the test of time — at least in the eyes of critics.
One such interview was with Hollywood star Jennifer Aniston. At first glance, it seemed like a typical talk show moment. But what if we look at it today?
I couldn’t help but compliment her legs
A newly resurfaced photo of Jennifer Aniston and David Letterman has reignited discussions about one of the most awkward moments on The Late Show.
The 2006 interview took place when Jennifer Aniston appeared on The Late Show with David Letterman to promote the romantic comedy The Break-Up, in which she starred alongside Vince Vaughn, who also co-wrote and produced the film.
The interview took an awkward turn from the start when Letterman fixated on Aniston’s legs, repeatedly complimenting them throughout the conversation.
Aniston, dressed in a black button-down blouse and black shorts, quickly became the object of Letterman’s admiration. He couldn’t help but praise her legs, and the cameraman followed suit, zooming in on them on screen.
‘That’s a stunning outfit,’ he remarked, then added: ‘And the reason it’s an amazing outfit is because you have amazing legs. Fantastic legs. You can only wear an outfit like this if you have beautiful, well-shaped, muscular, long legs.’
‘That’s an amazing outfit,’ he remarked, then added, ‘And the reason it’s amazing is because you have amazing legs. Fantastic legs. You can only wear an outfit like that if you have beautiful, well-shaped, muscular, long legs.’
The actress, clearly puzzled, tried to smooth things over by joking that she had worn shorts simply because of the heat.
Although Aniston always conducted herself with dignity, even she couldn’t hide her discomfort during one interview in which Letterman seemed fixated on her legs.
But Letterman didn’t back down. As the conversation progressed, he returned to the topic with another remark: ‘Your legs, you’ve got something there.’ This exchange made fans uncomfortable then — and even more so now.
As if that weren’t enough, he quickly changed the subject and began asking her about her rumoured relationship with Vince Vaughn. Letterman also asked Aniston if it was Vaughn’s idea for her to ‘appear nude in the film.’ Caught off guard, Aniston hesitated before dodging the question, suggesting Letterman ask Vaughn when he was on the show.
Couldn’t resist mentioning Aniston’s legs
Today, we know that Aniston began dating her co-star Vince Vaughn during the filming of The Break-Up. In a later interview, she revealed that he played a crucial role in helping her recover from her highly publicised divorce.
Speaking about Vaughn, Letterman couldn’t resist mentioning Aniston’s legs. ‘I can’t take my eyes off your legs, to be honest. You’ve got something there,’ he remarked.
Later in the conversation, he made another comment that seemed to refer to them, saying: ‘I hope someone at home is recording this on TiVo, because I can’t take my eyes off this shot.’ Although it wasn’t entirely clear which shot he was referring to, Aniston’s awkward expression suggested that it was another mention of her legs.
since we’re talking about david letterman being awful.. is anyone ever going to address this? pic.twitter.com/ZU5wIpsTFg
— ۟ (@aerynsreid) February 14, 2021
And this wasn’t the first time Letterman had made Aniston feel visibly uncomfortable. In a now infamous 1998 interview, he grabbed her by the neck and sucked on a strand of her hair. Aniston, clearly uncomfortable, wiped her hair with a napkin Letterman handed her.
He then handed her a napkin to wipe away the saliva, which only made the situation even more awkward.
Aniston handled the situation with dignity, as she has done many times throughout her career. Known for her ability to remain composed in any situation, she managed to continue the conversation.
Even after such an awkward moment, she later returned to The Late Show, proving once again that she can rise above even the most awkward situations.
Two years after her infamous ‘leg’ moment with Letterman, Jennifer Aniston returned to the show, this time in a chic pink dress that reminded viewers once again how stunning she is.
Images from this clip recently went viral on social media, but most people seem to have focused on Jennifer’s legs and overlooked what she is actually holding in her hand.
This time, the Hollywood icon showed off more than just her looks. While the actress was busy trying to dodge personal questions, including those about her relationship with John Mayer, she also found time to present the host with a thoughtful gift.
Aniston, who graced the cover of GQ wearing only a red, white and blue tie, presented the Late Show host with a gift during the promotion of her new film Marley & Me.
‘It’s an early Christmas present,’ she said with a smile.
Letterman wasted no time, took off his tie and, with Aniston’s help, put on the new one. She presented him with the Brooks Brothers tie she wore on the cover of GQ magazine, saying, ‘This is the pinnacle of my career.’ Letterman, proudly wearing the tie, joked, ‘Funny, the tie said the same thing during the photo shoot.’
‘This is so exciting, I’m dressing Dave!’ she exclaimed.
When the tie turned out to be a little short, Letterman joked, ‘You know what they say about guys with short ties.’
It was a humorous moment, and fans couldn’t help but gasp at this unexpected gesture.
Although Aniston never spoke out against such encounters, looking back, it becomes clear that these moments did not stand the test of time. What was once considered late-night humour is now sparking a new debate that is difficult to ignore.
