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Resurfaced clip of David Letterman making Lindsay Lohan cry during interview is still painful to watch

David Letterman’s 2013 interview is now making fans rethink how Lindsay Lohan was once treated on live TV

Back in 2013, Lindsay Lohan sat down with David Letterman to promote 'Scary Movie 5', expecting a routine Hollywood interview. 'The Late Show' had always been a go-to spot for stars promoting their latest projects, but things took an unexpected turn. Instead of solely promoting the film, Letterman went off-track, questioning Lohan about her rehab stints and legal troubles—topics that had made her a constant target at the time. Years later, when the clip resurfaced online, audiences saw it through a new lens. Many felt Letterman had crossed a line and called for an apology from him.

During the interview, the host asked Lohan, “Aren’t you supposed to be in rehab now? How many times have you been in rehab?” Lohan glanced off-camera multiple times before responding, “Several.” As reported by The Independent, Letterman then asked, “How will this time be different? What are they rehabbing, first of all? What is on their list? What are they gonna work on when you walk through the door?” Lohan then tried to be diplomatic and move on. “I think, to be honest, I’m happiest when I’m working, and the healthiest, and I think this is an opportunity for me to focus on what I love, and I don’t think it’s a bad thing. I think it’s a blessing."

Letterman continued to ask, “Do you have addiction problems? Is it alcohol? Do you drink too much?” As the audience burst into laughter, Lohan pointed out that rehab wasn’t part of the agreed-upon topics for the interview. Typically, guests are briefed in advance about what will be discussed, but Letterman appeared to have other plans. Determined to steer the conversation his way, he pulled out a printed list detailing Lohan’s past struggles. Without hesitation, she grabbed the paper, skimmed through it, and firmly told him to keep it to himself. She said, “You can’t make a joke of it. That’s so mean.” Lohan then told him he sounded like Dr. Phil.

Several social media users reacted to this clip on social media. One X (formerly Twitter) user said, "David Letterman should be canceled for the ashamed Lindsay Lohan’s interview in 2013. If this passed 9 years ago. Why this man is still doing shit live?" Another person commented, "David Letterman sitting a young Lindsay Lohan down for an interview and then saying 'aren’t you supposed to be in rehab' is so gross. the internalized misogyny in the media at that time and even now makes me sick... wtf." The conversation kept drifting off course, despite Lohan's attempt to redirect it back to her film, 'Scary Movie 5,' as reported by Glamour.

However, one X user shared a different part of the same interview and wrote, "People are pointing out that Letterman made Lohan cry, but OP’s clip edits out what he said that made her tear up. It’s rather deceiving. Here is the end of the segment." Meanwhile, amid the criticism directed at Lohan's interview, a 2021 Craig Ferguson monologue also became popular. As reported by Deadline, the former host of 'The Late Show' had taken a stance against offensive humor in the monologue, denouncing the media's insensitivity toward celebrities going through personal hardships and criticizing Britney Spears's harsh treatment.