Charlie Sheen's Career: What Went Wrong

It's hard to reconcile it when faced with the wild-eyed, ranting cautionary tale we're seeing and hearing online, on TV, and on the radio, but Charlie Sheen used to be a serious, respected actor. Really. Sheen was able to shift from weighty, Oscar-bait drama to good time comedy with ease, and his filmography is dotted with more than a few undisputed classics.

So what happened? The short answer: The 90s.

Once Sheen's personal life started to become more interesting than his increasingly putrid film roles, and he started simply playing versions of Charlie Sheen rather than characters, he started down the road to "winning." Which, of course, is now defined as "getting fired from your successful show."

Red Dawn (1984)
it's hard to believe there was a time when Sheen could be overshadowed by Patrick Swayze, C. Thomas Howell, and Powers Boothe, but in one of his earliest starring roles that was pretty much the case. Not that it was entirely Sheen's fault - his character, the younger brother of Swayze's former jock-turned-rebel leader, wasn't given much of anything to do. But his few scenes are memorable, mostly because of how natural Sheen seemed even given the extreme conditions of the movie. And we defy anyone not to get teary watching a weeping Swayze cradling Sheen's lifeless body on a playground swing set.

Lucas (1986)
What could have been a thankless role - dreamy high school quarterback - is given some surprising layers by Sheen in this story of a high school geek (the late Corey Haim) who has a crush on the girl (Kerri Green) who is in turn batting eyes at the QB. Sheen's "Cappie" isn't a locker-stuffing douche - he's sweet, charming, and likable. It's one of those rare movies where you don't mind who the girl ends up with.

Ferris Bueller's Day Off (1986)
What seemed like a one-off goof now seems oddly prescient. Sheen grinds "Bueller" to a halt - in a good way - with a one-scene cameo as a druggie bad boy who hits on Ferris' sister at a police station. It's hilarious, it's a classic, and it was the first glimpse of the bad boy lurking underneath the heartthrob. In retrospect, he was just a little too believable as a bleary-eyed punk who won't let a little thing like getting arrested keep him from hitting on women.

Platoon (1986)
Following the now cult-classic "The Wraith" (about a murdered teen who comes back from the dead with a supernatural car - yeah, it's terrible, but in that great B-movie way), Sheen leapt right into the A-List with the lead role in Oliver Stone's gripping Vietnam drama. Echoing his dad's "Apocalypse Now," Sheen may not have had the meatiest role (those went to Tom Berenger and Willem Dafoe), but he, once again, felt real and relatable and able to hold your sympathy throughout. He was clearly not a fluke.

Wall Street (1987)
Sheen reteamed with Stone for another gripping drama that once again, like "Platoon," asks Sheen to play the straight man to a more gloriously over-the-top character (in this case, Michael Douglas' Gordon Gecko). But Sheen nails it, selling each moment as his Bud Fox goes from hotshot rookie to Satan's right-hand man to hollowed out shell of his former self.

Eight Men Out (1988)
It looked like nothing but prestige movies from here on out for Sheen. After a minor blip in the slight but enjoyable "Young Guns," Sheen joined an impressive ensemble cast (John Cusack, David Strathairn, Michael Rooker, John Mahoney) in director John Sayles' ("Return of the Secaucus Seven," "Lone Star") take on the legendary 1919 "Black Sox" scandal. It's the type of elegantly-constructed period drama actors (and Academy members) love.

Major League (1989)
After a decade of legitimate career wins, Sheen took it to a new level by showcasing his surprisingly keen comedy chops. In this goofy but enjoyable (c'mon, you have to admit this movie has a lot of heart) comedy, Sheen is the motor that powers the story. Even years later, his entrance in the final game and showdown with Clu Haywood is a stand-up and cheer moment. Sheen plays a very serious-minded character hilariously, and that's not an easy thing to pull off.

Navy Seals (1990)

Whoo, boy. The new decade would not start out kindly for Mr. Sheen. When your movie is used as shorthand to explain how stupid people are, you know you've made a bad choice. Sheen played a macho bad boy in this half-assed "Top Gun" that pretty much falters on every level. It was a paycheck gig years before Sheen would actually need such a thing.

Men at Work (1990)
Teaming up with his brother Emilio for a slacker comedy probably seemed like a good idea at the time. But this slapstick-heavy story of two loutish garbage men discovering the body of a murdered politician is instantly forgettable. With a dearth of quality movies to focus on, the public began paying closer and closer attention to Sheen's personal life. This was also the year he released - we kid you not - a book of poetry called "A Piece of My Mind." It featured a disturbing cover illustration (a hand holding a bloody piece of scalp) and lines like "A night of drink/A night of hate/A night as dark/As last night's date." 

Hot Shots! (1991)
After completing another failed attempt at straight-forward action ("The Rookie," which even co-star Clint Eastwood couldn't salvage), Sheen thought perhaps comedy would come to his rescue. And, for a short period, it did. Spoofing his own and others' action adventures, Sheen actually succeeds in this Naked Gun-style all-inclusive spoof at a time back before the "Date/Disaster Movie" guys ruined that concept completely. It also paired Sheen with Jon Cryer, which would not prove insignificant.

Hot Shots! Part Deux (1993)
Yeah….once was fun. Twice? Not so much.

The Chase (1994)
An action comedy that is actually better than it has any right to be, "The Chase" really started Sheen down the path of playing characters who were basically "Charlie Sheen." And you could see the appeal for him - his ex-con character is a good guy who just happened to be in the wrong place at the wrong time (like, say, in Heidi Fleiss' black book). And given his ability to humanize even the most cartoonish characters, Sheen was still able to convince the public to go along with him on this.

Major League II (1994)
You know it's bad when even Wesley Snipes says "no thank you" to the sequel.

Terminal Velocity (1994)/The Arrival (1996)/Money Talks (1997)
Bland. Unremarkable. Uninteresting. Sheen is a million miles away from his 80s heyday at this point, and the cracks in his personal life are getting harder and harder to conceal.

Being John Malkovich (1999)
It's little more than a cameo, but Sheen officially gives in and just plays himself. Banking entirely on his bad boy party image (the fact that Malkovich "parties" with Sheen is a meant as a shocking revelation about the quote/unquote serious actor), Sheen can no longer plead misunderstanding. His Adonis DNA is rising to the surface.

Spin City (2000-2002)
With movies no longer as welcoming to Sheen as they had once been, Charlie found an opportunity on television. Michael J. Fox had to leave "Spin City" as his Parkinson's Disease worsened, and Sheen was brought on as a replacement character named….Charlie. He was also slick, charming, and a little forward with the ladies. Any sense of acting was clearly behind Sheen, even if his comedy timing was a good as ever.

Two and a Half Men (2003-2011)
Sheen's run on "Spin City" was over, but he seemed to find TV life agreeable. And why not? Less grueling schedule, easier shoots, characters that were basically PG versions of him. He would ride that magic formula for eight seasons with phenomenal success ("Men" is routinely among the highest-rated shows on TV - even after Sheen's many run-ins with the law and good taste), before the wheels came off. Well, to be honest, before Sheen took an enormous wrench and forcibly pulled the wheels off himself. With a good 20-odd years of hard-living between him and his ambitions as an "actor," Sheen blurred the lines between himself and his characters so thoroughly that it's really not surprising that his psyche went Col. Kurtz on him.


So is there a way back? At this point everything that worked for him - the ability to underplay characters, the ability to humanize characters, and the ability to seem grounded and real amid ridiculous situations - just can't be revived. It's like asking women to find Mel sexy again after years of seeing him drunk and abusive. The baggage is too big, and Sheen has checked out. Seeing as CBS has officially fired him from "Two and a Half Men," there seems to be only one outlet left for Sheen: Reality TV.

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