David Letterman had Lindsay Lohan in tears on "The Late Show" on Tuesday night, while the actress appeared to take his jabs at her legal woes in stride and laughed continuously through their awkward but humorous interview.
The host and comedian, known for poking fun at his guests, repeatedly asked the 26-year-old "Men Girls" star about her upcoming 90-day stint in rehab, a sentence handed down for a 2012 car crash case. It was one of several legal problems Lohan has faced over the past five and a half years, during which she has served time in jail and undergone treatment for substance abuse.
Check out 7 highlights from Lindsay Lohan's appearance on "The Late Show with David Letterman" on April 9.
1. David Letterman makes Lindsay Lohan emotional.
"I love seeing you," she told Letterman.
"I love seeing you, honestly," he replied, adding: "Oh, she's tearing up a little bit. God bless you."
He handed her a tissue.
"Thanks, make it obvious and all," she said.
Letterman then prepared to have a clip from Lohan's bedroom scene with Charlie Sheen in the upcoming film "Scary Movie 5" and the actress began to talk about it, but then said: "Sorry I'm flustered right now because you made me tear up 'cause you're very sweet."
2. David Letterman makes theft joke, Lindsay Lohan plays along.
In 2012, Lohan was put on informal probation until May 2014 for taking a necklace without permission from a Venice jewelry store. In March, a Los Angeles judge extended it for an additional two years after Lohan pleaded no contest to the car crash case charges and was issued her rehab sentence. She has until May 2 to show proof she has enrolled in psychological counseling and community labor.
"You know I have routinely made jokes about you," Letterman told her. 'Lindsay Lohan was on the Today show this morning. The appearance went well -- only one camera is missing.'
Lohan let out a high-pitched laugh and said: "That would be a lot for me to carry."
Letterman later asked, point blank: "Yes or no -- do you steal stuff?"
Lohan laughed and asked: "Do you?"
3. Lindsay Lohan talks about a planned joke that never happened.
Lohan arrived in a white and orange floral dress and told Letterman that she had originally planned on coming on the "Late Show" with the tag attached to it.
"And then you were going to cut it off," she told Letterman.
4. Lindsay Lohan makes an alcohol joke.
"We never thought we'd see you again, honestly, because of the jokes and stuff but yet you have enough spine, enough sense of yourself, enough poise to come out here and talk to me," Letterman told Lohan as his audience applauded.
Lohan then took a sip from her "Late Show" mug and joked: "Oh I thought this was going to be vodka. Shucks!"
"You've got to stop drinking. They don't let you drink in rehab," Letterman said.
"It was a joke!" she replied.
"I know! I wish you'd come out with the tags on your dress, though," he said.
5. Lindsay Lohan takes David Letterman's list of jokes.
With Letterman's permission, the actress at one point took from his band a piece of paper with notes and jabs about her.
"These are the appetizers up here, thesee are the main courses, there's your desserts at the bottom," he joked.
6. "We didn't discuss this in the pre-interview."
Lohan appeared a little uncomfortable after Letterman asked her "Aren't you supposed to be in rehab right now?" She said she begins her stint on May 2. He then pressed further.
"What are they rehabbing -- what are they gonna work on when you walk through the door?"
"We didn't discuss this in the pre-interview," she replied, adding: "No, I think to be honest, I'm happiest when I'm working and healthiest and I think this is an opportunity for me to, you know, focus on what I love in life and I don't think it's a bad thing. I think it's a blessing."
"Do you have addiction problems?" he asked.
"Now you sound like Dr. Phil," she replied, referring to her mother's awkward interview with Dr. Phil McGraw (check out 6 highlights).
"Did we really? Now I'm the one who's having the blackouts," he joked.
7. Lindsay Lohan is "looking forward" to rehab.
"I'm a target," she told Letterman. "I've always been and I've put myself in the past in situations where I, you know, I take full responsibility for it and it wasn't funny and I was being immature and I was going through a phase and I had a lot of family stuff going and things in life and you grow up and you mature and I've said that a million times and I know that."
Letterman, who had undergone therapy himself for depression, told her that she is "lucky" that she will get help in rehab."I am looking forward to it," she said. "I'm looking forward to taking time for myself and the next time I come on the show, that will be in my past."
She said that she hopes to become "happy and healthy" like Letterman, who said: "Well, I think you will be. That's what I'm saying -- you win by taking care of your life because people are rooting against you now. Now the best way to show them they're wrong is to turn it all upside down."
Check out a video of Lindsay Lohan's on "The Late Show with David Letterman" below.