The 35-page journal, which is up for auction, is a window into the actor's mind. Written when he was a 14-year-old student at Santa Monica High School during the 1979-1980 school year, it also foreshadows his future troubling behavior.
"Often I feel that I'm gonna go crazy. I really don't know why either. Maybe it's because of school or the world we live in today. I know it sounds kind of stupid but who knows maybe someday I'll just go whacko," he wrote in the first entry, misspelling wacko.
Sheen has been a virtual shut-in, according to TMZ, since his second goddess left. The website reported that his ex-wife Brooke Mueller has actually been spending time with him in his home and telling friends that there's even a possibility of them reuniting.
The former couple's divorce became official on May 2. Since then, they've gone to court multiple times to hammer out details of their custody agreement regarding their 2-year-old twin sons, Bob and Max.
According to TMZ.com, the child custody agreement between the former "Two and a Half Men" star, 45, and his most recent ex-wife, 33, does not require either of them to undergo drug testing.
Sheen famously lost his sitcom job after a January bender and told ABC News' "20/20" that he was "banging seven-gram rocks" of drugs while partying.
In his journal, the actor exhibited vengeful thoughts similar to the ones he would later unleash on his former "Two and a Half Men" producer Chuck Lorre.
In an October 1979 entry, he wrote, "People that act so hot should have their mothers raped by 7 Hell's Angels in front of them. That's not all. I also think they should be cut in half at a rate of 1 inch per second, and be viciously tortured for three straight days by means of fire."
Nate D. Sanders Auctions in Los Angeles is auctioning the worn blue spiral-bound notebook that has "Charlie Estevez," Sheen's legal name, written on the top right hand corner of the cover. The entries are legible in pencil and blue and black ink.
The auction, which ends Thursday, July 21st at 5 p.m. PST, also includes several of Sheen's poems, a letter and a drawing depicting a warlock.
"That warlock drawing is pretty neat," Nate D. Sanders told ABCNews.com. "And he's still talking about warlocks. I would think for most people what they're thinking at age 14 would change by age 44, but 30 years later, his personality is the same. It's definitely his."
Sanders said he acquired the journal from a memorabilia dealer in Orange County, Calif.
When asked about the diary, Sheen's rep responded: "Cannot confirm nor deny."
It certainly sounds like Sheen. In the notebook, the future lothario who would party with prostitutes and porn stars and live with two women he coined his "goddesses," fantasized about his "dream vacation" as "one with a harem of 40 beautiful girls all in Hawaii."
Sheen also ruminated about death and dying. "When I'm all alone, I think about death," he wrote in November 1979. "It's really weird. I mean you wonder what happens when you die."
He picked up the same theme later in the month. "How do I feel when I'm all alone -- well, it's weird, I kind of don't feel anything. A lot of times, I think about dieing," he wrote, misspelling the word.
Again, he speculated about what happens to a person after he dies. "Do you go to some magical palace and live in ecstasy all eternity or do you go into a state...of total pain?"
Just like he dismissed reports that he was bipolar earlier this year, Sheen pooh-poohed mental illness in his high school writings. "It's all in your head! Car sickness and mental diseases are all in your head. People just simply get carried away and think in exaggerated form and blow things up like a balloon," he wrote in a November 1979 entry.
As of Wednesday morning, the highest bid was $100. Sanders is expecting the journal to bring in a few thousand.