This is my cry movie. You know, the movie you can pop in and know 200% that you're going to cry to. I pretty much cry throughout this entire film. The relationship between Sam and Lucy makes my heart ache.
2. Dead Man Walking
Like a lot of Penn films, it's a hard movie to watch, but both Penn and Sarandon give amazing performances in this.
3. The Falcon and the Snowman
This drama/thriller marked the first serious Sean Penn movie I ever saw, and while it's flawed, there are glimmers of the talent he displays in later works. I actually watched this the first time because I was so in love with Timothy Hutton (who I still adore and finally get to see on my TV in Leverage lol).
4. Fast Times at Ridgemont High
No list would be complete without his breakout role, but it's funny seeing the new posters of this movie. He was nobody in a throwaway comic role, and yet, he is the one everybody remembers. Can you remember the other actors in this movie?
5. Milk.
As far as I'm concerned, he owns this movie.
6. Mystic River
There's much I love about this movie - the cinematography, Clint Eastwood's direction, the ensemble. But again, Penn is brilliant.
7. The Game
I like this for the movie's twists rather than specifically for Penn's performance. It's not aged well, but I still enjoy it.
8. 21 Grams
This is not an easy to watch. It's not told linearly, the performances are raw, and the emotions more so. But it's worth it anyway, for Benicio del Toro as much as for Sean Penn.
9. Carlito's Way
This movie is all about what a chameleon Penn really is. It's a fantastic gangster movie on its own, but Penn's performance is just as strong as Pacino's in my opinion.
10. State of Grace
I'll be honest. While Penn is good in this, my fond feelings for this film arise from his costar. Gary Oldman is one of those actors I've been obsessed with since his Sid and Nancy days. I've even sat through Coppola's Dracula too many times to count just because of him.
11. Racing with the Moon
I know. It's not really a great movie. But it was one of those gentler movies I fell in love with when I discovered it in college. Elizabeth McGovern was stunning, Nicolas Cage hasn't gone overboard yet on some of his acting shtick, and Penn is solid.
12. The Thin Red Line
I'll admit I've only watched it once, but that's not the movie's fault. It's a mesmerizing war movie, but war movies and I don't always get along. I find them difficult to live with, to be honest, and can't deal well with the emotions they churn. That being said, this is one of the better films in Penn's catalog.
13. Hurlyburly
Okay, this one's cheating. I don't really care for the movie, but I love the play so I have to include it.
What's your favorite Sean Penn movie?
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