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 (https://www.indiewire.com/features/general/10-actors-cut-from-terrence-malick-films-how-they-reacted-99568/ ) – 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:
- Mystic River
- The Thin Red Line
- Carlito’s Way
- 21 Grams
- 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 |
Love love him. Been a quite 20 years and it’s unlikely to change but can hope that there is some good stuff yet to come.
How would you rank the 21 grams trio? I think Penn is 3rd and Del toro takes the honors.
@AP- I think I’m with you on the 21 Grams rankings
Odd one but would you like to see him over Kyle MacLachlan in Lynch films?
@AP- Tough, Penn is a far better actor than MacLachlan but I don’t know- he has a certainly built in naivete that seems to work- especially in Blue Velvet
It is a stretch to call Walken a veteran actor in 1986.
@Malith- I get the point, but he’s over 40, 17 years older than Penn, and already has an Oscar. Your comment feels like a nitpick
@Malith- moving you to spam for the continued trolling. Please be polite.
I love seeing Carlito’s Way ranked so high. I posted this on Carlito’s Way page:
“I think Penn’s Dave Kleinfeld is underrated as a Villain, I am not saying that Penn’s performance is underrated as I think it gets its proper due. But Kleinfeld the character is severely overlooked in discussions on great Villains. I think this is partially because he’s an unconventional Villain given that he gradually becomes the films Villain. Carlito (Pacino) on the other hand is the opposite as he comes across as obnoxious and borderline delusional in that opening court scene while Kleinfeld is calm, cool, and collected. Kleinfeld’s charcter slowly descends into madness almost like Bogart’s character in Treasure of the Sierra Madre. The difference is Bogart’s Fred C Dobbs is primarly driven by greed while Kleinfeld is driven by greed as well but more so by his inferiority complex which again is an unusual trait of a great movie Villain.”
Penn has incredible range; I thought he was a strange choice for Milk (2008) when I saw previews for it back in 2007/2008. Hard to believe the same guy who played Jimmy in Mystic River (2003) played Harvey Milk in Milk. I feel like early Sean Penn had a Marlon Brando aura to him; an incredible raw intensity although he did not have the same sort of anti-authority/rebellious nature of Brando although much of that has to do with the time periods they acted in.
@James Trapp- These are some strong additions to the page – thank you for the comments here.
I was surprised to learn he has 22 archiveable films. He is mostly turning out duds than hits in the last 15 years apart from small roles in a PTA and Malick film. But then I realized he broke out very early in his early 20’s which is an unusual age for many great actors.