David Letterman's B-List Guest Went After His Notes After He Started Asking Questions That Were Not Approved (2024)

Lindsay Lohan rose to fame as a child when she starred in the Disney remake of The Parent Trap. Over the years, Lohan became a teen star when she starred in hit movies like Freaky Friday, Confessions of a Teenage Drama Queen, and Mean Girls.

However, her reputation as a bankable actress took a dive when her personal troubles took center stage.

It was right before a rehab stay that Lohan appeared with David Letterman on his late night show. During the interview, Letterman asked Lohan questions about her rehab stay, which she said weren't covered in the pre-interview.

Lindsay Lohan Stood Up To Letterman When He Asked Unapproved Questions During Their Interview

In 2013, Lindsay Lohan appeared on the Late Show with David Letterman to promote Scary Movie 5. However, Letterman was much more interested in her upcoming rehab stint and her addiction issues.

"Aren't you supposed to be in rehab?" Letterman asked. He also asked, "What are they rehab-ing? What is on their list? What are they going to work on when you walk through the door?"

This led to laughter from the audience.

Lohan told the audience that the two "didn't discuss this in the pre-interview." She also told Letterman, "I'm the happiest when I'm working. This is an opportunity for me to focus on what I love in life. I don't think it's a bad thing."

Letterman then asked Lohan several questions about her "addiction problems."

"Is it alcohol? Do you drink too much?" he asked.

Lohan then tried to redirect attention back to Scary Movie 5.

"We're here for a movie. Let's stay on the positive."

Lohan then read Letterman's notes, which included a list of her struggles and jokes he planned on making about them. While Letterman did offer Lohan words of encouragement, he eventually started talking about her recovery again.

Lohan eventually stood up to Letterman and said, "You can't make a joke of it. That's so mean. No. No, we're not doing that. This is my show now."

Charlie Sheen Spilled Secrets About Working With Lindsay On 'Scary Movie 5'

Lohan appeared with Charlie Sheen in Scary Movie 5. The actresses cameo appearance at the beginning of the movie was something Sheen himself advocated for.

"I gave her half of my salary on Scary Movie 5. I knew the scene would be much more epic if she took part in it," Sheen explained.

Sheen told The Daily Beast that producers initially offered him $500,000 to play himself in the film. However, when Lohan was added to the project, Sheen was told his salary would be cut to $250,000 in order to pay her. However, when Sheen asked Lohan how much she was making for the scene, she said only $100,000. The numbers didn't add up.

"So I just gave her $100,000 of their money," Sheen said. "Paying it forward."

Sheen later stated publicly that Lohan never even thanked him for the check he mailed to her. She reportedly sent him a bouquet of flowers to his home in Los Angeles after his public complaint.

Sheen also said that her lack of thanks didn't surprise him, because she wasn't very friendly on set. She also reportedly arrived only after producers sent her a private jet, because she missed a commercial flight from New York City to Atlanta.

"I felt bad for her," Sheen said. "I was with some of her team the night before making sure she got on this plane, and all I wanted to do was rehearse the scene with her one-on-one because I have a lot of experience in this genre. But I couldn’t get her to rehearse it, so we only met in the makeup trailer about five minutes before shooting. She was shy and vulnerable, but her instincts are dead on."

This wasn't the first time Lohan and Sheen had worked together. Lohan previously guest starred in Anger Management, a sitcom in which Sheen starred. Sheen's behind-the-scenes stories hinted at the partying that would send Lohan into rehab following her Letterman appearance.

Sheen spoke to The Kyle and Jackie O Show and revealed the hard-partying actress was no match for him. According to Sheen, a garbage bin was named after Lohan after she vomited into it following a night out.

"She’s a gangster. On the second day she stayed out too late. There was a garbage can we called Lindsay because that’s the one she puked into right before she did a scene with me."

Letterman Wasn't The Only One Who Hurt Lindsay By Joking About Her Past

In 2024, a new Mean Girls movie was released. Like the original from 20 years earlier, the film was the brainchild of Tina Fey. The new version of the story was also a musical, based on the successful Broadway production.

The film even included a surprise cameo from Lohan herself. When speaking to Entertainment Weekly, Fey shared how she scored the surprise cameo for the film.

"Paramount was like, 'Can you get any of the original ladies? And I was like, 'I can't fit five people in.' I felt like if I could only get one person as a surprise, the original movie is really Lindsay's movie," Fey told the outlet. "As great as they all are, she's the heart of that movie."

"And I thought, well, what could she do? I didn't think [she should] play a teacher. I was trying to think of something that you wouldn't expect," she continued. "And just to have her do that late in the movie, it also feels like it comes, I hope, at a time where fans weren't expecting one more little surprise. It also lets her be smart, which Cady is."

However, while Lohan appeared in the film and showed up to the premiere, she made it clear that she wasn't happy about one joke in the film.

During Megan Thee Stallion's appearance in the film, she says about Cady, "Y2K fire crotch is back." The line references a viral paparazzi video from 2006 where Brandon Davis referred to Lohan as "a fire crotch."

"Lindsay was very hurt and disappointed by the reference in the film," Lohan's rep said.