It looks like Charlie Sheen has a soft spot for wacko hoes in need because rumor has it that he’s planning on giving train-wreck Lindsay Lohan a job… and that’s besides the $100,000 he already gave her to pay off her debts.

TMZ is reporting that LiLo still owes the IRS over $100,000 and now the State of California is coming at her, because she didn’t give them any tax money in 2011. They want over $56,000 from her. That’s when Lindsay reached out to Sheen again, only this time he is making her work for it…

… and no, we don’t mean blowjobs.

LiLo will play herself on an episode of FX’s Anger Management. In the episode that airs in April, LiLo gets down with Charlie after meeting him in therapy.

This piece of news makes me feel two thing: Really old and a little scared for an innocent child.

Sheen is set to be a first-time grandfather after learning that his eldest daughter, Cassandra Estevez Huffman, is pregnant. Cassandra, 28, is the daughter of Sheen and his high school sweetheart Paula Speert.

Cassandra married Casey Huffman — her boyfriend since high school — during a ceremony at the Bacara Resort and Spa in Santa Barbara in September 2010.

Charlie’s ex-wife Denise Richards was responsible of announcing the baby news on Twitter Monday, writing:

“I guess some of you have heard… @charliesheen is going to be a Grampa…yes GRAMPA! His beautiful daughter Cassandra is gonna be a mama.”

Somebody bring Charlie Sheen a comfy chair because it could be a while before Lindsay Lohan thanks him for that $100K gift

Last night Sheen told Entertainment Tonight that La Loca Lohan never actually thanked him for the $100,000 he gave her recently to help with her IRS problems. “I’m still waiting for a text to say ‘thank you,’ anything. Anything,” he said playfully.

After the host suggested Linds may have been rendered speechless, Sheen added, “And fingerless.” Even so, he called her “a very good and decent young lady” who just needs some time to “get her [bleep] together.”

Lindsay Lohan was not the only charity to benefit from Charlie Sheen’s recent generosity

According to sources, Charlie donated all his Scary Movie 5 paycheck to three different charities… four if you include Lohan.

Sheen was paid $250,000 to show up for one day of shooting for the “Scary Movie” series — but for some reason, he didn’t want to keep any of the cash he made from the project, so he gave $100,000 to Lindsay Lohan — to help alleviate her crippling tax debt — and he donated the rest to three charities … as chosen by the movie’s director, producer, and one of the other filmmakers behind the flick.

It looks like Charlie Sheen and Lindsay Lohan have formed some kind of especial troubled-actor bond, because last week Sheen gave LiLo $100,000 to help her with her unpaid taxes

TMZ reports that the two got close while filming Scary Movie 5 in September, and talked about everything including the $233,904 Lindsay owes the IRS. According to sources, Sheen offered to help her out, but she refused; he sent the money to her business manager anyway and a grateful Lohan applied it to her bill right away.

Charlie Sheen is back in the news, but this time is for something good: He has pledged at least $1 million to military charity United Services Organization’s program for assisting wounded and sick soldiers and their families, reports Reuters.

Sheen is turning over 1% of the profits from his new show Anger Management and says the USO could get well over $1 million if the show is a big hit. His initial donation of $250,000 is one of the largest that the military charity has ever received.

“It’s an honor for me to be able to give back to these men and women of the military who have done so much for all of us,” Sheen said in a statement. “They put their lives on the line for us every day, and I’m just happy that my work on Anger Management can bring a little bit of relief to the troops and their families.” A USO spokesman praised Sheen’s generosity, saying “the way we lift the spirits of the families and troops is through generous donations from the American public. It is heart-warming to me to see how the American people support the troops whether it’s 25 cents or $25 or $250,000.”

Charlie Sheen premiered his new show “Anger Management” by taking shots at “Two and a Half Men” during the opening scene.

The very first scene of “Management” opens on a tight shot of Charlie (playing a character named Charlie) while he’s on an angry rant … saying, “YOU CAN’T FIRE ME, I QUIT!! You want to replace me with some other guy? Go ahead! It won’t be the same!”

He adds, “You think I’m losing! I’m not! I’m … anyway, you get the idea.”

When the camera pulls out, it reveals Charlie is only taking out his anger on an inflatable punching bag named BoBo … while teaching his group therapy class about an anger management technique.

Charlie Sheen recently gave out an interview in Playboy, telling the magazine his weird behavior was caused by a “psychotic break” after years in the spotlight and many failed relationships.

“I finally just said the things I had always been thinking.” But when he infamously said he was “winning,” the truth was far from it: “I was in total denial,” he says. “I felt I was winning by finally being able to speak my mind. I felt that was some sort of victory.”

That and other outbursts weren’t planned, he adds, they were “just random.” (Tiger blood? “I don’t know. It’s just a very dangerous animal. And there’s a tiger in Apocalypse Now, by the way, so maybe there’s a connection there.” Adonis DNA? “I don’t know what the f*** that was about. That was just stupid. That went a little far.”)

Now, he’s clean and sober, but having a “hard” time giving up prostitutes, he says: “Parts of it are soulless and parts of it are nourishing. It’s always a roll of the dice.”