best film:  It’s tempting to forget Sean Penn is in The Tree of Life. That’s not a good sign for him in terms of his impact on the film’s masterpiece status. I think of Jessica Chastain, Brad Pitt and young Hunter McCracken. But Penn is in it—though it’s not a major feather in his cap and I can’t call it a cameo. I do think (at least after two viewings) it’s slightly better than The Thin Red Line which would be the next best Penn film. Penn’s work here in the gorgeous World War II epic is much more substantive and affecting. The Thin Red Line is an ensemble film but Penn’s contributions are second only to Jim Caviezel in the cast.

best performance:  Mystic River. Penn is emotive and bombastic and he nails it. He has the posture of an ex-con, the anguish of an adoring father, and the stature and size of a crime boss. It’s a miraculous performance and deserving of the Oscar. It’s part of a wild 1-2 punch in 2003 for Penn with this and 21 Grams (excellent work in two of the best five films of the year—both so heavy).

stylistic innovations/traits:  Penn has 21 films in the archives and counting, Two Oscar wins (MILK and Mystic River) and five nominations. However, it’s not his best film (Tree of Life) nor his best performance (Mystic River) that get him into the top 40 on this list. It’s the depth and variety. He’s in two Malick films, plays Jeff Spicoli in Fast Times at Ridgemont High and chews the hell out of some scenery in two De Palma films (casualties of war, carlito’s way). He can do a chameleon-like disappearing act in a biopic (MILK) and carry a weaker Woody Allen archiveable film into the archives based on his performance almost single-handedly (Sweet and Lowdown). People hate Penn and performances like I Am Sam get some chuckles but he’s one hell of an actor. I also love how he doesn’t blink sitting across from great performances by Walken and Pacino in At Close Range or Carlito’s Way. Most actors, even good ones, would be getting their doors blown off.

directors worked with:   Malick (2), De Palma (2),  and then Woody Allen once along with Fincher, Stone, Van Sant, Eastwood and Iñárritu

Top 5 Performances:

  1. Mystic River
  2. The Thin Red Line
  3. Dead Man Walking
  4. MILK
  5. At Close Range



Archiveable films

1981- Taps
1982- Fast Times at Ridgemont High
1985- The Falcon and the Snowman
1986- At Close Range
1988- Colors
1989- Casualties of War
1990- State of Grace
1993- Carlito’s Way
1995- Dead Man Walking
1997- The Game
1997- U-Turn
1998- Hurlyburly
1998- The Thin Red Line
1999- Sweet and Lowdown
2000- Before Night Falls
2001- I Am Sam
2003- 21 Grams
2003- Mystic River
2004- The Assassination of Richard Nixon
2008- Milk
2011- The Tree of Life