best film:  It is tempting to forget Sean Penn is in The Tree of Life (2011). That is not a good sign for him in terms of his impact on the film’s masterpiece status. This has happened before with Malick where actors’ roles are significantly cut or they get left completely on the cutting room floor ( ) – and nobody can argue with the results when it comes to The Tree of Life. The film has plenty for Jessica Chastain, Brad Pitt, and young Hunter McKracken. Next in line in this category would be another Malick film – The Thin Red Line (1998). Penn’s work here in the gorgeous World War II epic is so much more substantive. The Thin Red Line is an ensemble film, but Penn’s contributions are right there at the top with Nick Nolte, Elias Koetas, and Jim Caviezel.


from The Thin Red Line (1998) Sean Penn and Jim Caviezel’s relationship and philosophical discussions are brilliant


best performance:  Mystic River. Penn is emotive, 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 is a miraculous performance. Sean Penn’s work in Mystic River is part of a wild one-two punch in 2003 for Penn with this and 21 Grams – excellent work in two of the best films of the year – both so heavy.


the camera elevates in 2003’s Mystic River to capture Penn’s suffering


stylistic innovations/traits: Sean Penn has twenty-two (22) films in the archives and counting, two (2) Oscar wins (Mystic and Milk separated by five years in the 2000s) and five nominations. However, it is not his best film (Tree of Life) nor his best performance (Mystic River) that get him into the top fifty (50) on this list. It is the depth (Dead Man Walking and Milk left off the top five performances below) and variety. Penn is in two Malick films, plays Jeff Spicoli in Fast Times at Ridgemont High and chews the hell out of some scenery in two Brian De Palma films (he particularly excels in 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). Penn does not blink sitting across from great veteran performers like Christopher Walken and Al Pacino in At Close Range or Carlito’s Way.


Penn in 2003’s 21 Grams – Penn’s archiveable career ranges for forty (40) years now from Taps (1981) to Licorice Pizza (2021) peaking in 2003 with both 21 Grams and Mystic River.


directors worked with: Brian De Palma (2), Terrence Malick (2), John Schlesinger (1), David Fincher (1), Oliver Stone (1), Woody Allen (1), Alejandro González Iñárritu (1), Clint Eastwood (1), Gus Van Sant (1), Paul Thomas Anderson (1)


from Carlito’s Way (1993) – Sean Penn plays a crucial role in the film as Kleinfeld. He is Carlito’s lawyer and friend. Nobody told Penn that his character is not the lead with his permed hair, glasses, inferiority complex and overcompensating hysteria. There is a reading of the film in which it is Carlito’s loyalty to Kleinfeld that causes his doom-  like a sort of non-sexual (even if there are lines like “if you were a broad, I’d marry you” during Carlito’s first night out of jail and both he and Kleinfeld ignore their dates) love story and noir femme fatale.


top five performances:

  1. Mystic River
  2. The Thin Red Line
  3. Carlito’s Way
  4. 21 Grams
  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
2021- Licorice Pizza