David Letterman Was Out Of Line Refusing To Promote A Guest’s Film, And Focusing On Her Troubled Personal Life Instead


  • David Letterman’s interview with Lindsay Lohan did not age well, as he ignored the pre-interview and focused on her troubled past, making her uncomfortable.
  • Fans criticized Letterman for his insensitive questions and behavior towards Lohan, praising her for handling herself well during the interview.
  • Letterman has had other problematic interviews with women, including asking Janet Jackson about her Super Bowl wardrobe malfunction and making inappropriate comments about the looks of his guests.

Looking back, David Letterman will always be remembered among the kings of late night interviews. However, not all of his interviews aged well looking back. Some are hard to watch knowing the struggles that his guests were going through. Fans felt sorry for Letterman’s now deceased guest, Farrah Fawcett, who was clearly intoxicated during their interview. Fawcett struggled throughout the interview and that started from the moment she stepped foot through the curtain.

As we’ll reveal in the following, Letterman had another guest who was struggling and, at the time, was just getting better. None other than Lindsay Lohan appeared on the show, and it seems like Letterman flipped the script on the actress, discussing her troubles instead of professional projects.

We’re going to take a closer look at how it all went down between the two, and why fans were upset with Letterman. In addition, we’ll take a brief look at other problematic interviews that took place on the Late Show.

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David Letterman Discussed Lindsay Lohan’s Rehab Stint Despite The Fact That It Wasn’t In The Pre-Interview

In terms of David Letterman interviews that aged poorly, this one might be the worst of the bunch. Lindsay Lohan appeared on the Late Show with the intent of promoting Scary Movie 5. However, David Letterman had a different agenda, refusing to discuss what was written in the pre-interview. Instead, Letterman decided to bring up Lohan’s troubled past, despite several hints throughout the interview that she was uncomfortable discussing the topic in public.

Letterman started the controversial moment by saying, “Aren’t you supposed to be in rehab?” Lohan responds, “We didn’t discuss this in the pre-interview.”

Credit to Lindsay as she’s then able to give a professional answer regarding the matter. “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,” she said.

“Do you have addiction problems,” Letterman continues. At that point, Lohan was clearly ready to discuss her film, and was upset at Letterman for making a joke out of her troubling situation.

RELATED – David Letterman Asked Billie Eilish If She Wanted To Stop Her Interview After She Started To Twitch Because Of Her Tourettes Syndrome

Things did not go well between the two and that was evident from the start when Letterman said, “you look remarkably well.” It was all a complete nightmare for Lohan and a moment that saw fans turn on David Letterman.

Fans Weren’t Happy With The Way David Letterman Conducted His Interview With Lindsay Lohan

Fans were not pleased with the outcome of the interview, especially the insensitive questions asked by Letterman. Over on YouTube in the comments section of the video, fans took aim at Letterman’s behavior, while praising Lindsay Lohan for the way she reacted.

Late Show host David Letterman interviewing Lindsay Lohan
via CBS

One fan wrote, “What’s crazy is he’s had her on the show since she was a child. How can he not think back on her as that child and be ashamed of the way he disrespected her. I think she tried to make this point too. When she said “I’ve been on this show since I was seven” Imagine behaving like this to someone you knew when they were just a kid and you were literally already a grown ass adult. For shame.”

As the fan notes, given their lengthy history together, it only made the interview that much worse to look back on.

Another fan writes, “Linsay won me over here. She tried her best to be poised and in my opinion, handled herself really well. I wish her the best.”

RELATED – David Letterman Rarely Showed Emotions, But He Broke Down Discussing Robin Williams On The Late Show

Great to see that, nowadays, Lohan is doing much better and isn’t making headlines for her past controversies.

David Letterman Has Lots Of Other Interviews That Aged Poorly

Letterman had a bunch of other interviews with women that went viral for their inappropriate nature. Business Insider revealed some of the very worst, which includes Dave asking Janet Jackson about her Super Bowl wardrobe malfunction, despite the fact that she clearly didn’t want to discuss, wanting to leave the moment in the past.

David Letterman
via CBS

Jackson told Letterman during the interview, “I don’t want to relive any of that. There are more important things to focus on in this world.” Still, Dave brought up the topic multiple times…

There are several other examples, including Letterman sucking on Jennifer Aniston’s hair, which is truly hard to watch. Letterman asking Jessica Alba for details about her outfit in Honey also deserves an honorable mention as extremely inappropriate. Fans have taken exception to David Letterman commenting on the looks of his guests in the past.

Clearly, a lot of Letterman’s Late Show moments haven’t aged all that well.

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