I’m trying to think like Charlie Sheen. It ain’t easy, but I’m trying.

The reason I’m trying is because, as commentators and bloggers sarcastically celebrate him as a pop culture hero, and critics and psychologists dismissively diagnose him as a delusional nutjob, I’m digging into what I, your average American guy, would do in his shoes.

As quoted by CNN.com, Dr. Lillian Glass, author of Toxic Men, explains the nationwide fascination with Carlos Irwin Estevez thusly: “It’s seeing somebody that has more than us, having less than us. We are watching this, and you feel like ‘Hey, I may not have the millions, but I’ve got my act together.’ ”

And yet, without thinking too hard (un-Sheen-like), I have to admit—nah, shamelessly state—that if I were Charlie Sheen, I just might be doing…the exact same things. Maybe not with as colorful a vocabulary—I’m not in the habit of saying “ordnance,” “charlatan,” or “warlock”—but still.

Now, it’s important to define 1) What it means to be “in his shoes,” and 2) What he’s actually doing now. Then we can 3) Reassess the situation. So…

1. In his shoes

We’re talking about a guy who grows up the son of a Hollywood legend in Malibu, stars on the Santa Monica High School baseball team, loses his virginity at 15 to a Vegas hooker (according to a recent GQ story), and shoots Super-8 films with buddies Rob Lowe and Sean Penn. After appearing in Red Dawn and Ferris Bueller’s Day Off, his career pretty much blows up with Platoon and Wall Street. He’s 22 years old. From there, his on-screen work rambles from drama (Eight Men Out) to action (Young Guns) to comedy (Major League) to TV (Spin City, for which he wins a Best Actor Golden Globe, and of course Two and a Half Men, for which he notches three Emmy nominations and which, The New York Times estimates, pulls in $250 million a year in revenue for Warner Brothers and CBS). Take his name off that résumé, and it sounds like a damn good run.

In between, he finds time to direct a documentary (Discovery Mars, which explores whether there is life on Mars), become a huge supporter and donor of Aid for AIDS, accuse the U.S. government of a 9/11 conspiracy and, oh, launch a children’s clothing line. (No joke. Visit sheenkidz.com.) Still sounds reasonably solid.

On the personal side, of course, things are murkier. The murkiest of the murky: Marries three times, fathers five kids. “Accidentally” shoots then-fiancee Kelly Preston in the arm. Frequents the brothels of Heidi Fleiss. Injects himself with cocaine, resulting in an overdose. And just in the past couple years, provokes multiple run-ins with the cops for everything from domestic violence to “criminal mischief” to causing a reported $7,000 worth of damage to his suite at New York’s Plaza Hotel. (It must be pretty nice. Can you imagine how much work it would take to do $7,000 dollars worth of damage to a Motel 6?) Hard to view this kind of stuff in anything but a negative light.

But even with all the drama surrounding him, he still spends the past seven years ruling his incredibly popular, painfully unwatchable CBS sitcom. And in 2010, he signs a two-year contract paying him a reported $1.8 million an episode. His net worth is estimated at $85 million. Dude’s got money to burn.


2. What he’s doing now

As noted by entertainment and sports journalist Chris Connelly on Bill Simmons’ B.S. Report podcast earlier this week, “Now we really know what F.U. money looks like…now we look it up in the dictionary and it’s going to be a picture of Charlie Sheen, from this era in his life.”

And he’s right.

We are looking at a guy with way more money than anyone needs, who’s found that candidly, aggressively speaking his mind on radio and TV only seems to multiply his fame. Phrases like “tiger blood,” “Adonis DNA,” “gnarly gnarlingtons,” “it’s just strafing runs in my underwear before my first cup of coffee” and simply “WINNING,” instantly become Internet memes. He signs up for Twitter, and sets a Guinnes World Record by hitting one million followers in just over 25 hours.

At the same time, he claims to be clean, having cured his addictions “in a nanosecond” with his mind. He owns two gorgeous LA homes, buys at least four exotic cars totaling nearly $800,000 in the past month (according to Access Hollywood) and flies around in a private jet (an F-18, bro?). He lives with two “goddesses,” 24-year-old porn star Bree Olson (come on, you don’t remember her from Big Wet Asses 10?) and 24-year-old graphic designer/model Natalie Kenly (biggest claim to fame before this: appearing on the cover of 420-friendly Cali Chronic X magazine).

And a few days ago, he demands a raise, to $3 million per episode on the show CBS has suspended in response to his rants.

3. Reassessment

Such behavior opens the door, as reported by CNN.com, for observers like Dr. Drew Pinsky to say, “The problem with him now is he’s getting so impaired psychiatrically that eventually…the psychiatric system is going to step in.” And for Dr. Mike Dow, an LA-based psychotherapist who appears on TLC’s My Strange Addiction, to say, “I hope that what we do on our show, which is actually help people, far outweighs the Charlie Sheens, which is really just a train wreck.” And for Dr. Glass to make her “I’ve got my act together” statement. None of these people, for the record, have personally examined Charlie Sheen.

It’s easy to paint him as irrational, immoral, irresponsible, insane, and there’s no overlooking the violent outbursts. Between the Preston shooting in 1990 and pleading guilty to third-degree domestic violence against third wife Brooke Mueller last year lie at least three other distressing incidents: allegedly striking a UCLA student he was trying to sleep with in 1994, allegedly beating porn star girlfriend Brittany Ashland in 1996, and numerous claims of abuse and a restraining order obtained by second wife Denise Richards when she filed for divorce in 2006. Sheen denies pretty much everything—”Women are not to be hit,” he tells Piers Morgan. “They are to be hugged and caressed.”—but there are too many instances to turn a blind eye, and I in no way condone violence against women. Unconscionable.

Still, the current Sheen hubbub isn’t about his mistreatment of women. If we were going to be outraged about that, we had the last two decades to tune the guy out. Instead, we make him a giant movie and TV star. No, this backlash springs from the fact that Sheen is currently saying and doing things that society claims to view as not “normal.”

And Glass’s words encapsulate what appears to be the en vogue theory about why we’re so engrossed with this man, that it’s all just voyeuristic schadenfreude.

But is that really what’s going on? Here’s where I have to step in.

I’m 32, never married, no kids. But taking all this information into account, I can attempt to picture myself as a 45-year-old, thrice-married dude with five kids, a gigantic bank account, ever-growing fame, and a fondness for neologisms.

And as the guy I am, I have to say that I am by no means fascinated with Sheen because “I’ve got my act together,” and he doesn’t. Nope, I’m fascinated because the guy has gobs of dough, he says and does what he pleases, and his toughest decision each morning is “Do I bang the porn star or the pot model first? Or…both at the same time?”

And on that note, let’s be honest with ourselves. Unless you, dear reader, are Robert Downey Jr. or Mickey Rourke, then you, like me, probably can’t fully comprehend what it’s like to experience Sheen’s lifelong level of access to money and drugs and fame and really hot sex. How can we even imagine what that’s like? Isn’t it a lot easier to resist such temptations when you’re not actually facing them on a daily basis? Who’s to say that if you did, you would be the picture of upstanding citizenry, rather than an outspoken, libidinous, addictive personality with your average mid-life crisis and a way bigger budget?

Certainly, I can’t answer that question for you. But I can answer it for myself. And where some—certainly being judgmental, perhaps hiding their own jealousy, possibly laying down with “ugly wives”—see a guy with a lot of problems, I can’t help but see a guy living the ultimate dude fantasy.

Is that so crazy?


(Steve Mazzucchi is Managing Editor of Made Man. Email him at smazzucchi[at]breakmedia.com.)