There's very little that ages well given today's constantly changing standards. For better or for worse, the culture has caused film and TV fans to reevaluate the stories, characters, and personalities they loved growing up. There's no doubt that this includes the actions of acclaimed comedian and late-night talk show host, David Letterman. For example, David made Jennifer Aniston incredibly uncomfortable when he repeatedly asked her about her legs on the show. Then there was the interview with Angelina Jolie that went so wrong that she never returned to his show again. In fact, David has had a number of uncomfortable interviews, including a handful with Lindsay Lohan. But there's one interview in particular that still has fans furious in 2022.
Lindsay Lohan's 2013 interview on The Late Show With David Letterman gained a lot of attention when fans rediscovered the video in 2021. Thanks to TikTok and Youtube, fans could see just how uncomfortable the interview got. With the lens of the growing social movements of the past decade and of the attention on the #FreeBritney movement, fans were furious about how David treated his guest. While many of the jokes he made during the interview were funny back then and are still funny now, other moments were downright cringe-worthy. Here's why fans are still talking about this awkward, uncomfortable, and somewhat shameful interview that resulted in Lindsay Lohan crying on national television...
David Letterman Couldn't Stop Talking About Lindsay Lohan's Rehab Experiences
The interview started with David being honest about "routinely" making jokes about her public image and her battle with alcoholism. He also admitted that he knows some of the stories about Lindsay that were circulating in the press weren't true at all. David then began to read some of the jokes he had written about her, some of which actually made Lindsay laugh. He is a comedian, after all. At this point in the interview, Lindsay seemed to be game with making fun of herself and her history of allegedly stealing things. But then things took a turn...
"Now, aren't you supposed to be in rehab?" David asked. Lindsay immediately became uncomfortable but gave him a date when she would return to deal with her addiction issues. Seeing an opportunity for a newsworthy and entertaining interview, David asked her numerous questions about her repeated stays at rehab.
"How will this time be different? What are they rehabbing? What is on their list? What are they going to work on when you walk through the door?" he asked her.
Lindsay was very clearly uncomfortable at this point, doing her best to stay calm and collected when faced with a sensitive subject she wasn't happy talking about. On top of this, Lindsay reminded David that she was there to promote a movie, Scary Movie 5. She even called him out for trapping her on-air with the questions. They were not, after all, discussed in the pre-interview.
Even though she was undeniably uncomfortable, Lindsay answered his question graciously and honestly, stating that rehab was going to be
an "opportunity to focus on what I love in life."
David Letterman Continued To Hammer Lindsay Lohan To The Point That She Started Crying
"Now do you have addiction problems?" David asked immediately after Lindsay gave him an answer that both shut the subject down and yet was honest.
"Now you sound like Dr. Phil," Lindsay stated sharply.
"I'm sorry. Is it alcohol? Do you drink too much?"
"We've discussed this in the past."
"Did we? See, now I'm the one having the blackouts. I outta be in rehab. What is wrong with me?"
"We are here for a movie," Lindsay said, shutting down the topic again. But when David made a joke of her response, Lindsay started to throw around a few self-deprecating jokes herself. This seemingly trapped her in an increasingly uncomfortable conversation.
While Lindsay delicately tried to balance comedy with honest responses, her level of discomfort was so obvious that the audience could feel it. But David still wouldn't let up. By the end of the interview, he tried to pay her an honest compliment for being brave enough to come on his show and face such ridicule. But the damage was done and Lindsay started to well up.
Since the interview resurfaced in 2021, fans of Lindsay have called out David for being "misogynistic", "vile", and adding to the "stigma of addiction and rehab".
Even still, some fans pointed out that headlines that claimed that David made Lindsay cry were deceiving. While almost everyone believes David crossed the line with his relentless jokes about her addiction, they claim he actually made her cry when he gave her a compliment. Whether or not critics of the interview will see it the same way is another story entirely. At the very least, this interview has gone down as one of the most cringe-worthy in his history.
