Top 5 Movie Guide: Sean Penn

For this edition of the Top 5 Movie Guide, we turn our attentions to one of the stars of this weekend's "Gangster Squad"Sean Penn. Penn, who is one of the most dynamic actors of our time, may also be known equally as much for is eccentric personal life and outward political views. His short temper is well documented by the community service hours he's racked up over the years, but he also happens to be one of the most decorated actors working today. Penn started out in the early-1980's, appearing in a hodgepodge of different films. Many were praised - such as his breakout role as Jeff Spicoli in "Fast Time at Ridgemont High - while others were panned.

The 1990's, however, saw Penn as a much more mature and a accomplished actor. He seemingly couldn't miss in the decade, which brought him his first two Academy Award nominations for performances in "Dead Man Walking" (1995) and "Sweet and Lowdown" (1999) - to date, Penn is the only person outside of Woody Allen himself to win an acting Oscar for a Woody Allen-directed film. In the new millennium, Penn has continued his high-profile career, racking up three more Academy Award nominations. He did not win 2001 for "I Am Sam", but has since brought home the last two in which he's been nominated for, "Mystic River" (2003) & "Milk" (2008) - he is currently one of only eight other actors to have won two Best Actor Oscars.

Penn continues to act in films, but as he's aged, he's noted his disinterest in the craft, and said that he'd prefer to only direct from here on out. It doesn't look like we're quite there yet, but at this point, any one of these films could be his last. For now though, hit the jump to see which titles made our lists!

Alex Schopp -
I don't really know why I've never cared much about Penn's career, but for some reason or another, he's never resonated with me. I can enjoy most of these films, but I've never once went out of my way to see a Sean Penn performance.

     1. Fast Times at Ridgemont High (1982)

Other than the moment at the end with Spicoli and his teacher, I really don't like this character. But the rest of the film is really solid; one of the better 80's coming-of-age movies. If you haven't seen it recently, go back and re-watch it. I feel like a lot of people might like this mostly on principle, but if you go back, you'll see how good it really is.
     2. Mystic River (2003)
Not necessarily the most pleasant of films, but the performances are all very powerful. This was one of my favorite movies of 2003.
     3. The Game (1997)
A solid thriller.
     4. 21 Grams (2003)
This is a well-crafted ensemble drama. I like the style and cinematography of the film, and I feel like it's definitely worthy of a watch. That being said, it's a bit long, and a little dry, so you're probably not gonna be coming back to this one on a regular basis.
     5. Casualties of War (1989)
Outside of the pop culture-ness of his Spicoli role, this one might stand out to me more than most of his others. War films aren't some of my favorites, but Penn's performance is great.

Ben Foutch -

     1. Fast Times at Ridgemont High (1982)

     2. State of Grace (1990)

     3. Casualties of War (1989)

     4. Mystic River (2003)

     5. Bad Boys (1983)

Derek Clem -

     1. Casualties of War (1989)

He's such a feral creature in this movie.
     2. Fast Times at Ridgemont High (1982)
I want to see a movie about their high school reunion. What would Spicoli be up to today?
     3. Taps (1981)
Penn's intensity, along with Cruise and Hutton, was an obvious display of some fine future acting careers. (okay, maybe not so much with Hutton, but he already grabbed his Oscar, so why try after that?)
     4. Hurlyburly (1998)
I like that his voice sometimes slips into a Jerry Lewis impression.
     5. Carlito's Way (1993)
I like to look back at this movie and think what the 'Three Stooges' movie would have been like had Penn played Larry.

Nathan Hinds -
The biggest thing I associate Sean Penn with is that I was pissed off both times he won an Oscar for Best Actor. I was strongly pulling for someone else both years. He did not deserve to win over Mickey Rourke in 2008.

     1. I Am Sam (2001)

     2. Fast Times at Ridgemont High (1982)

     3. Mystic River (2003)

     4. The Tree of Life (2011)

     5. U-Turn (1997)

Andy Schopp -
I have little passion for this list and that seems unfortunate. I just felt like everything was a plateau of a movie except for the tiny bit of "nostalgia" I have for my first selection.

     1. The Game (1997)

     2. I Am Sam (2001)

     3. The Thin Red Line (1998)

     4. Mystic River (2003)

     5. The Tree of Life (2011)

So there we have it, folks. A really good variety this week, but maybe that shouldn't be much of a surprise considering the subject of this post is one of the most acclaimed actors of our time. Still though, 14 different films showed up above, and six with multiple selections. Surprisingly, no film found its way onto all five lists this week, though we did have two with four selections. Both "Fast Times at Ridgemont High" and "Mystic River" accomplished this feat, though it was Fast Times that also earned two first-place votes ("Mystic River" did not receive any). Both are entertaining films, and, generally speaking, sort of bookend Penn's filmography. He's had more notable roles since 2003, but "Mystic River" is one of his more recent films, and Fast Times was obviously hos breakout film. Both are very worthy of a watch or two if you never got around to seeing them.

"Casualties of War", the Sean Penn/Michael J. Fox film, was the only title that received three picks this week. A solid war film, and both Penn and Fox provide great performances. Otherwise, "The Game", "I Am Sam", and "The Tree of Life" rounded out the titles which received multiple selections, each with two.

Plenty to choose from this week, so dig in and get yourself more familiarized with all that Penn's filmography has had to offer over the years. As always, we hope that each of these selections helps guide you to better and more enjoyable all-around viewing experiences.

Happy watching!