Top ten Charlie Sheen movies

It has been a long time since I have written a top ten list. The recent Charlie Sheen fiasco and a conversation I had on Twitter about Sheen’s roles has prompted me to put together a list of my favorite films from his 30+ year career. While I have not a huge fan of Two and a Half Men, I do like a number of his roles on the big screen. Keep reading to see my list and be sure to share your thoughts!

Please keep in mind this list features films that are not the best or even great. Many of the roles are also small parts, so here we go.

Sheen stars as a “rebellious inmate in an Army stockade” opposite his father, Martin Sheen and Laurence Fishburne in this 1990 film. I fist saw this drama on HBO and really enjoyed it. If you haven’t seen this, it is worth a viewing.

Sheen stars as the leader of a car thief ring opposite D.B. Sweeney. Forget THE CHASE, this has the best driving scenes. Not a great movie, but a decent Sheen flick. 
Wesley Snipes, Tom Berenger, Corbin Bernsen, Rene Russo and Dennis Haysbert star in this baseball comedy classic. The first film was good, the rest horrible. I am not sure why they want to reboot this franchise, but oh well.
If you are a huge baseball fan than this ensemble drama based on historical events would be at the top of your list. EIGHT MEN OUT stars John Cusack, D.B. Sweeney, Christopher Lloyd, David Staitharn and Michael Rooker in “a dramatization of the Black Sox scandal when the underpaid Chicago White Sox accepted bribes to deliberately lose the 1919 World Series.”
This is my favorite Sheen comedy, I like it better than HOT SHOTS and THE CHASE. This chemistry on screen between Sheen and his brother is great. It reminds me of the relationship that Ashton Kutcher and Sean William Scott had in DUDE, WHERE’S MY CAR?. It is really an aimless film, but one that really stands out in his career to me.

Sheen and Estevez starred on screen in this biopic “of notorious Mitchell Brothers who opened up a successful San Francisco strip club and thriving porn business that lead to a downward spiral of power and greed.” I have only seen this once, but when I watched it I couldn’t stop watching. Check it out when you get a chance, it is a pretty decent film.

I know this is the smallest Sheen role on the list, but it is iconic in a classic film. Sheen played the drugged out police station detainee that talked some sense into Ferris’ sister played by Jennifer Grey.  
This is one of my favorite ensemble action films of the 80’s. What is not to love about a movie that combines, Sheen, Patrick Swayze, C. Thomas Howell, Lea Thompson, Jennifer Grey, Harry Dean Stanton and Powers Boothe, This is actually one remake I am interested in seeing. Not because I think it will be a better film, but because I want to see how the film has dealt with changing the Cold-War theme. This is a must watch film in my opinion.
Aside from APOCALYPSE NOW, this is the best film dealing with the Vietnam war. I loved Sheen’s performance as Chris, “a young recruit in Vietnam faces a moral crisis when confronted with the horrors of war and the duality of man.” The film also starred Willem Dafoe, Tom Berenger, Tony Todd, Forest Whitaker, Keith David, John C. McGinley, Kevin Dillon and a young Johnny Depp. If that is not an amazing cast I don’t know what is. 

Sheen played a “young and impatient stockbroker is willing to do anything to get to the top, including trading on illegal inside information taken through a ruthless and greedy corporate raider (Michael Douglas) whom takes the youth under his wing.” This is one of his best performances. It is a shame that Stone felt compelled to make a sequel. This film still is one that I can watch over and over again. Sheen’s best years for film were 1986 and 1987!

Do you agree with my rankings? Which films did I leave off? Share your thoughts below. 
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Jim Napier

Jim Napier

Lover of movies and The Big Lebowski.