24 Hours of Movies: Charlie Sheen Part II

by Patrick Bromley

Another marathon of movies from my guy!
A few months back, I published a 24-hour marathon of Charlie Sheen movies after watching much of his filmography in the span of a couple of weeks and declaring him one of my guys. There were so many titles I wanted to include but didn't have the space for that I decided to program a second marathon. This is that marathon. Thanks to Rosalie Lewis and Andy Ginestra, we're calling this one "The Sheening." You're welcome and I'm sorry.

10 am - Red Dawn (1984, dir. John Milius)

Sheen's first real movie (outside of a small part in Grizzly II: The Revenge, which was shot in 1983 but wasn't released until 2020) casts him as one of a group of high school students who form a militia when their Colorado town is invaded by Soviets. I want to start here because it's basically the start of Charlie Sheen's career, but also because I have something of a complicated relationship with this movie: I watched it and wrote about it years ago, pretty dismissive of it as the jingoistic ravings of writer/director John Milius (a filmmaker I really like). Then I watched it again when Shout! Factory put it out on Blu-ray and liked it quite a bit more. This viewing can be the tiebreaker. 

12 pm - Good Advice (2001, dir. Steve Rash)

The fascinating thing about 2001's Good Advice is that it's a romantic comedy, and Charlie Sheen is not really the romantic comedy type. At least he's playing to type as a wealthy scumbag stock trader (because Wall Street) who's down on his luck and starts ghost writing his girlfriend's (Denise Richards) advice column in secret. Complicating Good Advice's chances for success is the fact that Sheen is playing opposite Angie Harmon, who is also not especially well suited to romantic comedy, and the pair don't generate a ton of chemistry together even when they wind up being cute. Despite its shortcomings, I still like this movie! Like so many generic romcoms, it's corny but charming and I like the actors even if they're somewhat miscast. In terms of Charlie Sheen mythology, Good Advice is especially important because it's the movie on which he met Denise Richards; the two would marry and have two children together.

1:30 pm - Eight Men Out (1988, dir. John Sayles)

Charlie Sheen's other, more respectable baseball movie (of the non-Major League variety, I mean) tells the story of Chicago's disgraced "Black Sox," the team that accepted bribes to throw the 1919 World Series. He plays "Happy" Felsch, one of eight players who conspired with gamblers and organized crime to lose the Series. Though he doesn't get a ton of screen time or as much backstory as D.B. Sweeney's Shoeless Joe Jackson, Sheen is memorable because he's still fresh-faced and innocent on the surface but also seems like a guy who would gladly take the easy money. Though this is arguably writer/director John Sayles' most commercial film, it wasn't as widely praised and respected as the rest of his filmography upon release. That's a shame because it's very good.

3:30 pm - Shadow Conspiracy (1997, dir. George P. Cosmatos)

I like that we're only four movies in and have already programmed four totally different kinds of movies. This thriller from the great George P. Costmatos (Tombstone, Cobra) essentially marks the end of Sheen's theatrical run before he would pivot primarily to DTV movies. He's a Presidential aide who gets caught up in a -- you guessed it -- conspiratorial power grab by others in Washington and pairs with a reporter (Linda Hamilton) to uncover the truth. It's an honest attempt to make a 1970s-style paranoid thriller, but it's much more Murder at 1600 than it is The Parallax View. That's not such a bad thing. As someone with a soft spot for '90s thrillers like this, I'm glad my boy Charlie got a turn at bat. Unfortunately there doesn't appear to be a good R1 Blu or even a DVD for this one, meaning it's all but forgotten. This would be perfect for Kino Lorber to pick up.

5:30 pm - The Big Bounce (2004, dir. George Armitage)

This is a murdered movie. Director George Armitage's long-awaited follow-up to his great Grosse Pointe Blank is a remake (of sorts) of a 1969 movie starring Ryan O'Neal, itself an adaptation of a 1969 Elmore Leonard novel. Shot as a hard R (it originally was slapped with an NC-17), the movie was whittled down to a PG-13 by producers hoping to recoup an investment and doomed the project in the process. The cast is pretty great, led by Owen Wilson at his loosest as a beach bum and Sara Foster in what should have been a star-making performance as a slinking bombshell. Sheen has a supporting role as a dummy who is seduced by Foster and tricked into doing some dumb crime shit. I suspect there's a good movie in here that got stripped out and left with this shell. It's still an entertaining shell.

7 pm - A Glimpse Inside the Mind of Charles Swann III (2012, dir. Roman Coppola)

I watched this for the first time when programming this marathon and I'm glad I did, as it's probably the last best role that Charlie Sheen is going to get. He plays an artist who is hospitalized after his girlfriend (Kathryn Winnick) leaves him; his life thrown into upheaval, Charles calls upon his friends (Jason Schwartzman and Bill Murray) for help. Roman Coppola is an eccentric guy and Charles Swan III is an eccentric film, but it seems to have been written with Sheen in mind, which is kind of sweet given the public flameout the actor had just a year prior. It seems right that we program this in the primetime slot and sort of build our entire marathon around it.

9 pm - Platoon (1986, dir. Oliver Stone)

I held off on programming this one -- Charlie Sheen's biggest break to date and his official arrival to mainstream stardom -- during the first marathon because, well, it's a downer. But downers can also be very good movies, and Platoon is a very good movie about the experience of fighting in Vietnam written and directed by someone who actually served in the war. Sheen was just a fresh-faced kid when he was cast as the lead in this one, a young soldier fighting in the jungle and torn between two father figures (Tom Berenger and Willem Dafoe). I assume his casting had at least something to do with his father having starred in Apocalypse Now, but his performance goes beyond legacy nepotism and, like Wall Street would do a year later, capitalizes on the central dichotomy of Charlie Sheen -- the conflict between his aw-shucks innocence and his much darker impulses, the handsome actor who's also an addict and a bit of a scumbag. Platoon places him at the center of this tug-of-war.

11:00 pm - No Code of Conduct (1998, dir. Bret Michaels)

The short-lived "Sheen Michaels Entertainment," a production company formed by Charlie Sheen and Poison frontman/sentient STD Bret Michaels, is responsible for producing this cop drama starring Sheen and directed by Michaels. The movie is one cliche after another, but it's not badly made and has enough wannabe director/film school flourishes to give it some energy and style. It's totally standard DTV stuff, elevated by a cast that also includes Martin Sheen as Charlie's father and superior, Meredith Salenger as Charlie's estranged wife (of course), Mark Dacascos as his partner, and Paul Gleason as a dirty cop. How Sheen and Michaels got so many names to sign on to this one will forever be a mystery, but it will play well late at night when we want to turn off our brains.

12:45 am - Machete Kills (2013, dir. Robert Rodriguez)

The absolute best part of Machete Kills, the messy follow-up to Robert Rodriguez's 2010 Grindhouse spin-off Machete, is not just the casting of Charlie Sheen as the President of the United States but also the choice to bill him as "Introducing Carlos Estevez." He's got little more than a glorified cameo in the movie (because of how Rodriguez shoots these movies, everyone feels like a guest star), but he's very funny in his straight-faced approach to the insanity of it all. I wish Rodriguez had been less jokey this time around -- the movie pretty much announces up front it's not going to be as good as its predecessor (which was just ok) in its opening minutes -- but as a midnight movie we could do a lot worse.

2:45 am - Bad Day on the Block (1997, dir. Craig R. Baxley)

I was torn on what to program here because Charlie Sheen made movies with two of my favorite genre directors, Albert Pyun (Postmortem) and this one, the start of his DTV era (era) which finds him working with one of the great action directors of the late '80s and '90s, former stunt coordinator Craig R. Baxley (Action Jackson, Stone Cold, I Come in Peace). I decided to go with Bad Day on the Block (aka Under Pressure) after watching some of Postmortem on Peacock. It's rough. Bad Day on the Block is the better of the two movies, casting Sheen as a firefighter who terrorizes the people around him, including his neighbors (Mare Winningham and David Andrews), who he blames for turning his wife against him. Sheen gives good crazy and Baxley serves the material well; while it's not great, it's fun to see the two working together.

4:15 am - Three for the Road (1987, dir. Bill L. Norton)

Speaking of not great, this is not a great a movie but our pickings are slimmer in this second marathon. This one has a short runtime (about 80 minutes) and will go down easy, affording us the opportunity to squeeze in some more Sheen before we call it a day (and a night). Here he's a straight-laced college student interning for a senator and tasked with bringing the politician's troublemaking daughter (Kerri Green) to an institution. He brings his buddy Alan Ruck along for the ride so that the title will make sense. Sheen reportedly signed on for a very different movie, one that was rewritten after he joined the project. I can believe it.

5:45 am - Scary Movie 3 (2003, dir. David Zucker)

I'm not the biggest fan of the Scary Movie franchise, but at this point in our marathon when we're totally sleep-deprived and delirious it's probably good to have this kind of gag-heavy comedy to jumpstart us back to life. The spoof, the first directed by Airplane!'s David Zucker (taking over for Keenan Ivory Wayans), is basically The Ring crossed with Signs. Sheen plays the Mel Gibson Signs role of a former minister whose property is invaded by aliens, while returning Anna Faris handles the Ring stuff. As funny as I think Sheen can be, he doesn't have the best material to work with in this one and winds up outclassed by Faris and Simon Rex as wannabe rapper brother, because 8 Mile. 

7:30 am - Cadence (1990, dir. Martin Sheen)

After a run of subpar Sheens in our marathon, we're bouncing back with this 1990 drama. That's right: the same year that he was directed by his brother Emilio Estevez in Men at Work, Charlie Sheen acted for his dad Martin Sheen (who also stars) in this, his lone feature directorial effort. He plays a rebellious soldier sentenced to 90 days in a military stockade run by Martin Sheen; a battle of wills ensues. Cadence finds Sheen doing really interesting work, balancing the innocence and earnestness he showcased in something like Platoon with the rebel streak he began cultivating in the late '80s and early '90s. The results are a surprisingly effective drama with exactly the right vibes for this point in our marathon. There's some race stuff in the movie with which director Martin Sheen doesn't seem willing to fully engage, but the movie means well. That counts for something.

9:15 am - The Chase (1994, dir. Adam Rifkin)

We end things, as we do, with a banger. Writer/director Adam Rifkin's biggest studio effort casts Sheen as a convict who kidnaps heiress Kristy Swanson and goes on the run, leading massive numbers of cops, camera crews, and wannabe heroes in pursuit. Rifkin's style is as broad and manic as ever and the satire of the news media is blunt and obvious, but The Chase is incredibly funny and entertaining in an overly-caffeinated sort of way. Sheen holds the center as the innocent man wrongly accused; he and Swanson are a lot of fun as an unlikely couple, as is the insane supporting cast that includes the likes of Ray Wise, Claudia Christian, Henry Rollins, Anthony Kiedis, and Flea. I love the idea of wrapping up our marathon with this wild a ride.