Sean Penn's best performances

Realized a while back that I had only seen a few of Sean Penn's films, so I'm currently havning a Sean Penn marathon where I watch his movies, and here I will rank his performances.

Movies excluded from my marathon are:

Summerspell (1983) small part and nowhere to find
Judgment in Berlin (1988) - Couldn't find it
Loved (1997)
Hugo Pool (1997)
Pauly Shore is dead (2003)
Persepolis (2007)
What Just Happened (2008)
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1.
The Assassination of Richard Nixon (2004)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Based on real life events, Assassination is set in 1974 and centers on a businessman who decides to take extreme measures to achieve his American dream. (95 mins.)
Director: Niels Mueller
“ The title scared me a little, but this is a great character study with an amazing performance. Taxi Driver light. ” - johan
 
2.
Milk (2008)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
The story of Harvey Milk, and his struggles as an American gay activist who fought for gay rights and became California's first openly gay elected official. (128 mins.)
Director: Gus Van Sant
“ Acting at its best. In my experience actors portraying homosexuals tend to act over the top by being "too gay" to make it credible. This performance is not to be placed in that tray. Penn made an honest, almost perfect achievement in acting as he won the Oscar for portraying politician/gay rights activist Harvey Milk's life during the seventies. ” - johan
 
3.
The Falcon and the Snowman (1985)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
The true story of a disillusioned military contractor employee and his drug pusher childhood friend who became walk-in spies for the Soviet Union. (131 mins.)
“ Didn't like the movie that much and it hardly engaged me at all, but Penn is brilliant. ” - johan
 
4.
She's So Lovely (1997)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
Maureen is pregnant and her husband Eddie is missing. Nervous, Maureen shares a couple of drinks with neighbor Kiefer... (100 mins.)
Director: Nick Cassavetes
“ Expecting a horrible film thanks to the title, i started watching this when I lacked something better to do in the middle of a summer night. But I was pleasantly surprised, and believe me I am rarely pleasantly surprised... this is indeed a odd film with very.. interesting dialogue throughout. Sean is great as a man released from a 10-year visit at a mental institution. ” - johan
 
5.
Bad Boys (1983)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Chicago crime kid Mick O'Brien is sent to reform school after accidentally killing a rival's kid brother. (123 mins.)
Director: Rick Rosenthal
“ Great early Penn-movie with an equally great Penn. ” - johan
 
6.
I Am Sam (2001)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A mentally handicapped man fights for custody of his 7-year-old daughter, and in the process teaches his cold hearted lawyer the value of love and family. (132 mins.)
Director: Jessie Nelson
“ There are many opinions on Sean Penn as Sam, personally I've seen it a few times and I must admit I cried at some point every time. I think this is a beautiful film with a beautiful performance! ” - johan
 
7.
Sweet and Lowdown (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman. (95 mins.)
Director: Woody Allen
“ Penn's unsympathetic character makes a great pillar to build a city of "mean comedy" on. ” - johan
 
8.
U Turn (1997)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A man heading to Vegas to pay off his gambling debt before the Russian mafia kills him, is forced to stop in an Arizona town where everything that can go wrong, does go wrong. (125 mins.)
Director: Oliver Stone
“ Some similarities to "She's so Lovely", again an unpredictable film which I liked really much. Love how Penn takes on these odd roles, he played brilliant here too. I feel the urge to praise Oliver Stone a little aswell for very intriguing directing. ” - johan
 
9.
Mystic River (2003)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
With a childhood tragedy that overshadowed their lives, three men are reunited by circumstance when one has a family tragedy. (138 mins.)
Director: Clint Eastwood
“ Penn shines along with the rest of the great cast. ” - johan
 
10.
Carlito's Way (1993)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A Puerto Rican former convict, just released from prison, pledges to stay away from drugs and violence despite the pressure around him and lead on to a better life outside of N.Y.C. (144 mins.)
Director: Brian De Palma
“ Penn is really good as Carlito's coke-addicted lawyer (and I can ensure you this is the worst haircut he's ever had). ” - johan
 
11.
Dead Man Walking (1995)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A nun, while comforting a convicted killer on death row, empathizes with both the killer and his victim's families. (122 mins.)
Director: Tim Robbins
“ I admire how Penn can change his voices like this and still sound believeable (compared to his latest film Carlito's Way where he has a high-pitched voice). This lower voice fits his character well just a small detail in his first Oscar-nominated performance. ” - johan
 
12.
21 Grams (2003)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A freak accident brings together a critically ill mathematician, a grieving mother, and a born-again ex-con. (124 mins.)
 
13.
State of Grace (1990)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Terry Noonan returns home to New York's Hells Kitchen after a ten year absence. He soon hooks up with... (134 mins.)
 
14.
This Must Be the Place (2011)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
Cheyenne, a retired rock star living off his royalties in Dublin, returns to New York City to find the man responsible for a humiliation suffered by his recently deceased father during W.W.II. (118 mins.)
 
15.
We're No Angels (1989)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
Two escaped cons only prayer to escape is to pass themselves off as priests and pass by the police blockade at the border into the safety of Canada. (106 mins.)
Director: Neil Jordan
 
16.
At Close Range (1986)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
In 1978 rural Pennsylvania an absentee father is reacquainted with his estranged teenage sons and they become intrigued with romanticized life of crime. (111 mins.)
Director: James Foley
 
17.
Taps (1981)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
Military cadets take extreme measures to insure the future of their academy when its existence is threatened by local condo developers. (126 mins.)
Director: Harold Becker
 
18.
Fast Times at Ridgemont High (1982)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A group of Southern California high school students are enjoying their most important subjects: sex, drugs and rock n' roll. (90 mins.)
Director: Amy Heckerling
“ It's a stupid and stereotypical character, but a funny one that I would've liked to see more of. ” - johan
 
19.
Hurlyburly (1998)
    1 2 3 4 5 6 7 8 9 10 5.8/10 X  
Hollywood movers and shakers dissect their own personal lives when everything seems to clash together. (122 mins.)
Director: Anthony Drazan
 
20.
All the King's Men (2006)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Based on the Robert Penn Warren novel. The life of populist Southerner Willie Stark, a political creature loosely based on Governor Huey Long of Louisiana. (128 mins.)
Director: Steven Zaillian
 
21.
Racing with the Moon (1984)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
In 1942 California, two young men await induction into the U.S. Marines and say goodbye to their girlfriends. (108 mins.)
“ Very enjoyable little film though he doesn't stand out as much as in his other early films. Still liked it a lot, a little treasure! ” - johan
 
22.
Fair Game (2010)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
CIA operative Valerie Plame discovers her identity is allegedly leaked by the government as payback for an op-ed article her husband wrote criticizing the Bush administration. (108 mins.)
Director: Doug Liman
 
23.
The Tree of Life (2011)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
The story of a family in Waco, Texas in 1956. The eldest son witnesses the loss of innocence and struggles with his parents' conflicting teachings. (139 mins.)
Director: Terrence Malick
 
24.
The Game (1997)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A wealthy banker is drawn into a dangerous game where the lines between the game and his real life become more and more blurry. (129 mins.)
Director: David Fincher
 
25.
Colors (1988)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
An experienced cop and his rookie partner patrol the streets of East Los Angeles while trying to keep the gang violence under control. (120 mins.)
Director: Dennis Hopper
 
26.
The Interpreter (2005)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Political intrigue and deception unfold inside the United Nations, where a U.S. Secret Service agent is assigned to investigate an interpreter who overhears an assassination plot. (128 mins.)
Director: Sydney Pollack
 
27.
The Thin Red Line (1998)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Terrence Malick's adaptation of James Jones' autobiographical 1962 novel, focusing on the conflict at Guadalcanal during the second World War. (170 mins.)
Director: Terrence Malick
“ A fine piece of art though the cast is too big for an actor to really stand out individually. But that's not a complaint, it woluld've been wrong if one of the actors were able to stand out from the others. ” - johan
 
28.
Casualties of War (1989)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
During the Vietnam War, a soldier finds himself the outsider of his own squad when they unnecessarily kidnap a female villager. (113 mins.)
Director: Brian DePalma
“ Unfortunately Penn's performance feels a little over the top here. I can see how the crew thought he would be perfect for the part though. ” - johan
 
29.
Gangster Squad (2013)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
It's 1949 Los Angeles, the city is run by gangsters and a malicious mobster, Mickey Cohen. Determined to end the corruption, John O'Mara assembles a team of cops, ready to take down the ruthless leader and restore peace to the city. (113 mins.)
Director: Ruben Fleischer
“ Not a very good performance. ” - johan
 
30.
The Weight of Water (2000)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A newspaper photographer, Jean, researches the lurid and sensational axe murder of two women in 1873... (113 mins.)
Director: Kathryn Bigelow
 
31.
Before Night Falls (2000)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Episodic look at the life of Cuban poet and novelist, Reinaldo Arenas (1943-1990), from his childhood... (133 mins.)
Director: Julian Schnabel
“ Just a cameo ten minutes in as a cuban farmer. ” - johan
 
32.
Shanghai Surprise (1986)
    1 2 3 4 5 6 7 8 9 10 3.0/10 X  
Glendon Wasey is a fortune hunter looking for a fast track out of China. Gloria Tatlock is a missionary... (97 mins.)
Director: Jim Goddard
“ Neither the film nor the actors are 2.8-bad, though... they are pretty bad. Why did they have to make this movie... ” - johan
 
33.
It's All About Love (2003)
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  
It's All About Love is the story of two lovers and their attempts to save their relationship in a near-future world on the brink of cosmic collapse... (104 mins.)
 
34.
Crackers (1984)
    1 2 3 4 5 6 7 8 9 10 5.0/10 X  
Garvey is a San Francisco pawnshop operator. His unemployed and criminal friends Dillard, Turtle, and Weslake... (91 mins.)
Director: Louis Malle
“ Terrible film where Penn has a very anonymous role. ” - johan
 
35.
Up at the Villa (2000)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
Superficial people are revealed and drastically changed by circumstance or luck in this a tale of death... (115 mins.)
Director: Philip Haas
“ Do not ever watch this movie, regardless of the circumstances. ” - johan