Angelina Jolie Never Appeared On David Letterman’s ‘Late Show’ Again After This Awkward Interview
Angelina Jolie might've taken a few subtle shots at David Letterman throughout their interview years ago.

David Letterman is considered a legend of the late-night game, however, he is also regarded as a polarizing figure, given the way some of his interviews have gone.
In truth, some of them have aged really badly, including his time alongside Paris Hilton, or sucking on Jennifer Aniston’s hair.
Letterman underwent more than a few bizarre interviews, though this one alongside Angelina Jolie is very peculiar, especially given the fact that she never returned.
In truth, fans think Jolie was teasing and subtly ripping David throughout the interview. In addition, some fans weren’t too pleased with David’s questions for the star.
Angelina Jolie Had A Tough Past Before Climbing The Mountain In Hollywood

Angelina Jolie underwent a tough childhood. She failed to create friendships, according to the star, because of her look and mother’s income compared to the rest of her schoolmates.
In addition, as a teen, the actress suffered from insomnia along with an eating disorder. She would also self-harm herself to ease the pain of her life.
Acting turned out to be the escape, but at times, even that became troubling. In recent years, Jolie has opened up about her past struggles, which include a traumatic experience alongside the now-disgraced Harvey Weinstein.
“If you get yourself out of the room, you think he attempted but didn’t, right? The truth is that the attempt and the experience of the attempt is an assault,” she said.
“I was asked to do ‘The Aviator’, but I said no because he was involved. I never associated or worked with him again. It was hard for me when Brad did,” she said.
Thankfully for Jolie, her ex-husband Jonny Lee Miller was great throughout the experience. Though the two would ultimately go their own ways, they did so on amicable terms. However, on David Letterman’s show, things began to go south when he was brought up.
David Letterman Brought Up Touchy Topics When Angelina Jolie Clearly Looked Uncomfortable

The interview got off to a rocky start when Letterman asked Jolie if she cooks or bakes, only for the actress to say sarcastically, “No, I’m not a good woman Dave.”
Things would get that much more awkward when Dave made a comment on Jolie’s smell, “You smell great, you smell nice, that’s a lovely fragrance, I appreciate that.” Angelina would awkwardly respond, “Anything I can do.”
The interview finally seemed to get back on track, that was until David brought up the question about marriage, asking Jolie if she was married. Jolie paused and stated that she was in the process of getting a divorce from her first husband, Jonny Lee Miller.
The two got hitched when the actress was only just getting into her 20s. Letterman tried to offer some advice, claiming that his marriage didn’t work out either given that he was too young at the time. Jolie just looked on without saying much following the advice, making mention that the experience had brought them closer together instead.
More awkwardness to follow when the conversation of Jolie’s tattoos came up. Angelina revealed that she wasn’t going to climb on Dave’s desk and show them off… yikes, she was likely throwing some shade his way.
The short interview would finally get back on track with Jolie ever so briefly speaking about her newest film. Nowadays, the interview resurfaced and fans weren’t too pleased with Dave’s questions.
Fans Were Upset With David Letterman Looking Back At The Interview Years Later

Like so many other David Letterman interviews, this one resurfaced years later after the fact. Dave does have a bumpy track record when it comes to certain interviews, especially alongside female celebs.
Nonetheless, for the most part, fans roasted Letterman while applauding Jolie for keeping her composure. Here’s what the YouTube fans had to say.
“He’s so inappropriate, but she handles it so well. So quick-witted, charming, and beautiful.”
“Anyone with an emotional IQ higher than a telephone pole would be able to tell she was uncomfortable and by ignoring it and thinking with the wrong head, Letterman was disrespectful and unprofessional.”
“I think her decision to underdress and wear her hair all back and wear black was deliberate- it’s almost a protest like maybe she really didn’t like him and was forced to go to promote the film.”
Was Angelina Jolie sending a message during the interview? Who knows, but what we know for sure is that she would never return again.