I think we all knew this was coming! I typically wouldn’t do a Sheen list but since I just did an Arnie list based on him being in the news, I figured I’d keep with the totally topical Top 5 theme. I must admit that I’m kind of glad I did. Recently on the podcast, I said I wasn’t a big fan of Charlie Sheen films, with a few exceptions, but he’s actually been in a lot of great films that I had completely forgot about. I also think my choices may surprise you a bit. So, I present you with my Top 5 Carlos Irwin Estevez films. Here they are (in order):

SIDENOTE: Ferris Bueller’s Day off is being excluded from this list! While FBDO would easily make my Top 3, Charlie’s part is so small that I hardly think it fair to judge it as one of “his” films.


I’ll be honest, I don’t expect most people to have this on their Top 5. It may also seem a bit out-of-place considering there’s no Platoon on this list. However, it has always been a bit of a guilty pleasure for me. I think I love it for the same reason I love Over the Top. That is, the premise (being that 2 garbage men foil a nuclear waste dumping and murder conspiracy and earn the love of the woman they pervertedly spy on) is so ridiculous that I have to love it.


Doug Benson has a great joke that goes something like this: If money never sleeps, it should try watching Wall Street 2: Money Never Sleeps! While the follow-up to this film failed on numerous levels, the original succeeds for trying to do essentially the same thing. That being to shine a light on the exploits of the greedy financial climate of its time. Along the way, it also managed to create one of the greatest cinematic villains of all time and turn in a very entertaining film… a strange feat for Oliver Stone.


WOLVERINES!!! Does anybody not love this film? This movie completely capitalizes on the “Red Scare” and paints a portrait of a group of young Americans who go all militia and turn the tables on an army of invading Rusky forces. It’s kind of great too because it’s one of those 80’s movies that cast a bunch of young actors (this is actually listed as Sheen’s first feature film on IMDB) that all went on to be successful actors, if not stars. What up, Swayze?


You have to love the movies about the rag-tag group of misfits that don’t get along but find a way to bury their differences and come together for a common goal. In this case, winning the American League pennant. This film, of all 5 listed, Sheen should actually get the most credit for propelling it on to the list. Ricky “Wild Thing” Vaughn is a great character played spectacularly by Sheen. I must admit, when he gets called on the field at the end of the film, and his music starts to play, I get chills every time I watch it. Oh, the film is really funny too!


THE MOST UNDERAPPRECIATED WESTERN EVER MADE! It could’ve failed very easily. A group of young hot actors in a rock ‘n roll, popcorn version of a film from what is considered a dead genre. Lord knows the formula has been tried, and failed, since. American Outlaws anyone? Still, this film just manages to get it right and make westerns fun again! Now, Sheen is a bit out-of-place in this one as he plays a guy with a stick up his ass but it was still a nice turn in a great film.

Got an actor you’d like me to cover for Top 5 films? Drop a suggestion in the comments and I’ll see what I can do!

14 Responses to “TOP 5 MOVIES: CHARLIE SHEEN”

  1. What? No love for Hot Shots? Sacrilegious.

  2. I’ve not seen any of these films, because I’m all about losing…

    I’m just glad Platoon wasn’t on here. That film was awful.

  3. Bruce Wayne Says:

    Being John Malkovich. Eight Men Out. Platoon. Wall Street. Major League. Ladies and gentlemen, there is you’re top five.

  4. Editor In Chief Says:

    I just realized I haven’t seen any of these movies. “Carlos Irwin Estevez”?! Kai, you might be the funniest person on the planet!

  5. […] Kai lists his top 5 Charlie Sheen movies (The List) […]

  6. Now THIS list? I am in 100% agreement with. Nicely played, Kai.

  7. I don’t know how many more Sheen movies I could name that aren’t listed here. Let’s see…Hot Shots 2, Major League 2 (he’s not in the third, is he?), Terminal Velocity, that alien invasion one…uhh….The Rookie….The Big Bounce.

    Yeah, I’m calling for The Big Bounce. It’s not even very good, but it’s an Elmore Leonard adaptation and has Morgan Freeman.

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