Charlie Sheen Once Gave Lindsay Lohan A Striking Amount Of Money

A Charlie Sheen and Lindsay Lohan friendship may make sense to some and be confusing to others. Both have had a complicated past with drug abuse and getting into legal trouble, so they have a lot of things in common. Even before they officially met, Sheen offered the "Mean Girls" actor advice on her recent troubles in 2011. According to ABC News, the "Two and a Half Men" actor told "The Dan Patrick Show," "I have some things I think she [Lohan] should consider, cause I don't tell anybody what to do. Work on your impulse control ... just try and think things through a little bit before you do them." Because both actors had a similar past, they got along great when they officially met.

The pair first met when filming "Scary Movie 5" and Sheen instantly connected with Lohan. A source had revealed to the National Enquirer, Sheen had a "soft spot" for the "Mean Girls" actor. In 2017, Sheen even shared with "The Kyle & Jackie O Show" that he and Lohan went out partying one night, and she outlasted the actor, per the Associated Press. He said, "I invited her over one night ... I out-drank her, or she out-drank me. And she literally tucked me in. I got tucked in by Lindsay Lohan. She kissed me on the cheek and said 'Sleep well, young prince.'" And it turns out, the two actors got close enough to not only share kisses on the cheek but also thousands of dollars.

One of Lindsay Lohan's struggles with the law was the amount of money she owed to the IRS. According to Forbes, "The Parent Trap" actor owed "nearly a quarter of a million dollars" for her taxes in 2009 and 2010. Apparently, the debt had gotten so large that Lohan's bank accounts were even seized. The large sum she owed was high, but Charlie Sheen was willing to help.

In 2012, E! News revealed that Sheen had given Lohan $100,000 toward her debt. The actor's rep shared, "[Sheen] has a long history of helping out his friends in many ways, and this is just another example of that." The "Two and a Half Men" star later confirmed the news to CNN and clarified it wasn't just for taxes. Sheen joked, "I thought I was going to get it back." He then explained the crew on "Scary Movie 5" was willing to give him a large payout, but not Lohan. He continued, "They said we want to hire Lindsay to make the scene more epic, but we want to give her half of what we gave you, we need to take it back ... they shorted her 100 on what I thought they were going to, so I made up the difference. That's all it was. And then she went public and talked about the tax debt." Whatever the reason behind giving Lohan $100K, it was still incredibly generous, and she had to be grateful.

November 2012 was when Charlie Sheen gave Lindsay Lohan $100,000, but it took nearly a month for the "Freaky Friday" star to thank her "Scary Movie 5" costar. Obviously, Lohan had a lot of things going on at the time that she received Sheen's gift, but if someone gave you that much money, you'd expect at least a thank you, and so did Sheen. In early December 2012, Sheen revealed to ET that Lohan never acknowledged him for the gift, per ABC News. He said, "I'm still waiting for a text to say 'thank you.' Anything, you know?" Well, it seems like the call-out in the media worked because not long after Sheen put Lohan on blast, she finally thanked him.

According to TMZ, less than a week after Sheen made comments about Lohan's apparent ungratefulness, "The Parent Trap" actor decided to send a gift back to the "Two and a Half Men" star. Lohan ended up sending Sheen a bouquet of flowers alongside a thank you card for his generous gift. A source even revealed the reason behind the delay of gratitude, sharing the actor broke her phone and lost all her contacts in the process, including Sheen. Even if her phone hadn't broken suddenly, she still had her onslaught of legal troubles to deal with, so we don't blame Lohan for forgetting to send a thank you.