Lindsay Lohan, 26, welled up and had to dab her eyes with a tissue at one point, after being given a surprising compliment by David Letterman.
“We’d never thought we see you again honestly because of the jokes and stuff,” David Letterman told the actress, after several awkward minutes of her laughing along with his gags about her shoplifting charges and multiple court appearances.
“But yet you have enough spine, enough sense of yourself, enough poise to come out here and talk to me.”
Lindsay Lohan couldn’t contain her emotion, with tears welling in her eyes, prompting David Letterman to hand her a tissue.
“Oh thanks, that makes it obvious and all,” Lindsay Lohan said, holding the tissue up to the audience.
“She’s tearing up a little bit. God bless you,” said David Letterman.
Lindsay Lohan then tries to introduce a clip featuring herself with Charlie Sheen in the forthcoming Scary Movie 5, but ended up being unable to get the words out, while trying to describe the excerpt.
“There’s a lot of things in the scene,” the actress said.
“I’m flustered right now because you made me tear up because you’re very sweet.”
Earlier, Lindsay Lohan confirmed to David Letterman she is heading to rehab on May 2, before being subjected to an uncomfortable grilling about her prospective treatment.
“I think it’s a blessing and not a curse,” she said about her treatment.
“To be honest, I’m the happiest when I’m working and the healthiest. I think this is an opportunity for me to focus on what I love in life.”
Sporting an orange and white floral dress with her hair in a loose updo, Lindsay Lohan tried her best to deflect David Letterman’s questions during the chat.
“Aren’t you supposed to be in rehab now?” David Letterman asked the star who last month struck a plea deal over charges relating to a car crash in June 2012.
“Don’t you watch anything that goes on? What are you a tabloid now?” Lindsay Lohan retorted, imploring the talk show host to concentrate on discussing her acting projects.
But David Letterman didn’t let her off the hook that easily, asking her how long she was going to be in rehab for and how many times she had been treated previously.
“Several,” Lindsay Lohan acknowledged about her forthcoming sixth time in rehab where she will spend three months.
“What are they rehabbing?” asked David Letterman, to audience laughter.
“What is on their list? What are they going to work on when you walk through the door?”
“We didn’t discuss this in the pre-interview,” Lindsay Lohan replied.
“Just saying to everyone.”
“Do you have addiction problems?” the host persisted.
“It is alcohol. Do you drink too much?”
“Now you sound like Dr Phil,” the actress said.
“We’ve discussed this in the past.”
At one point, Lindsay Lohan took David Letterman’s list of questions and read them out herself, ending with the one: “Why are you always in trouble?”
“I don’t know,” she declared.
“I couldn’t answer that. I’m a target. I’ve always been. I put myself in situations in the past where…I take full responsibility for it. And it wasn’t funny. I was being immature. I was going through a phase. And I had a lot of family things going on and things in life.
“You grow up and you mature and I’ve said that a million times, I know that,” she continued.
“But what else am I supposed to say when it’s a process of life and I’m not trying to deny any situation I’m put in.”
“You’re lucky that we have this rehab that you’re looking forward to, before you got hurt and someone else gets hurt,” said David Letterman.
“I agree – I’m looking forward to it,” Lindsay Lohan said.
“I’m looking forward to some time for myself. The next time I come on the show, that will be in my past.”
David Letterman then expressed surprise that the actress had actually turned up to be on the show.
“I showed up! Like I wasn’t going to!” she said.
“Who’s taking you to rehab?” the host then asked.
“Oh God. Jimmy Fallon, and you,” Lindsay Lohan responded before correcting herself.
“I don’t want people to think I’m making a joke of that. I’m not. It’s no joking matter.”
However, Lindsay Lohan sportingly laughed her way through several of David Letterman’s jokes about her woes, even cracking a few at her own expense.
Sipping from a mug on his desk, she declared: “Oh I thought this was going to be vodka. Shucks!”
David Letterman began the chat by showing the audience a photograph of Lindsay Lohan’s first appearance at 6-years-old in 1992.
He then proceeded to read out several jokes about her.
“Lindsay Lohan’s in court so often, the cafeteria has named a sandwich over her,” he declared.
The star joined in, revealing she had planned to appear on the show with the shop tags still on her dress.
“That would have been tremendous,” agreed David Letterman.
“What in life can’t we make light of?”
“I’m fine with making light of myself,” Lindsay Lohan agreed.
“That’s why I want to walk out with a tag on.”
Lindsay Lohan was also quizzed about her friendship with Charlie Sheen – she recently filmed a guest appearance on his sitcom Anger Management.
“I met Charlie when I was doing Scary Movie 5 in Atlanta,” she recalled.
“He told me about the show that he was starting to do and it all came together. It’s a really great set. Nice environment. Everyone’s so funny.”
David Letterman also alluded to Charlie Sheen’s claim that he wrote Lindsay Lohan a cheque for $100,000 to help pay her tax bill.
“Is it true that Charlie gave you money or is that not true?” he said.
“That’s something you’d have to ask Charlie,” Lindsay Lohan retorted.
Despite the rather testing interview, Lindsay Lohan looked in good spirits as she left the studios, having changed into a lather mini-shirt, black lace sleeveless top and strappy sandals.
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