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Top 10 Sean Penn Movies:  From Philosophical To Action-Packed And Fans Should Not Miss Them

Top 10 Sean Penn Movies: From Philosophical To Action-Packed And Fans Should Not Miss Them

Sean Justin Penn (born August 17, 1960) is an actor, director, screenwriter, and producer from the United States. For his performances in the mystery thriller Mystic River (2003) and the biopic Milk, he has received two Academy Awards (2008).

Tobey Strickland
Last updated: Oct 09, 2021 | Oct 08, 2021

Table of Contents

Sean Justin Penn (born August 17, 1960) is an actor, director, screenwriter, and producer from the United States. For his performances in the mystery thriller Mystic River (2003) and the biopic Milk, he has received two Academy Awards (2008).

Leo Penn started his acting career on television with a cameo in episode 112 of Little House on the Prairie, directed by his father, Leo Penn, on December 4, 1974. Following his cinematic debut in the drama Taps (1981), he went on to star in a variety of films in the 1980s, including Fast Times at Ridgemont High (1982) and Bad Boys (1986). (1983). "

Penn's performances in the crime dramas At Close Range (1986), State of Grace (1990), and Carlito's Way (1991) earned him critical acclaim (1993). With the drama Dead Man Walking (1995), for which he received his first Academy Award nomination and the Best Actor Award at the Berlin Film Festival, he established himself as a renowned leading actor.

Penn earned two more Oscar nominations for Woody Allen's comedy-drama Sweet and Lowdown (1999) and the drama I Am Sam (2001), before winning his first Academy Award for Best Actor for Mystic River in 2003 and his second for Milk in 2008.

He's also received two Best Actor Awards at the Venice Feature Festival, for the independent film Hurlyburly (1998) and the drama 21 Grams, both directed by Nick Cassavetes (2003).

Penn made his feature film directorial debut with The Indian Runner (1991), which was followed by The Crossing Guard (1995) and The Pledge (2001), both of which garnered positive reviews. Penn directed one of the 11 parts of 11'09"01 September 11 (2002), a compilation film created in the aftermath of the September 11 terrorist attacks.

Into the Wild (2007), his fourth feature film received critical praise and two Academy Award nominations for its biographical drama survival film.

Penn's political and social activity includes his criticism of the George W. Bush government, his meetings with the presidents of Cuba and Venezuela, and his humanitarian efforts in the wake of Hurricane Katrina in 2005 and the 2010 Haiti earthquake.

Sean Justin Penn (born August 17, 1960) is an actor, director, screenwriter, and producer from the United States. For his performances in the mystery thriller Mystic River (2003) and the biopic Milk, he has received two Academy Awards (2008).

Casualties Of War (1989)

Filmgoers had already seen a growing list of films about the wretched aftermath of the Vietnam War by the time Brian De Palma's Casualties of War arrived in 1989, including dramatic hits like The Deer Hunter, Apocalypse Now, and Platoon, as well as action-driven blockbusters like the Rambo trilogy — which may go some way towards explaining why they didn't show up for Brian De Palma's Casualties of War.

Casualties was a critical success, with critics lavishing praise on Penn and expressing surprise admiration for Fox's powerful dramatic performance. However, the film lost money at the box office, despite praise from scribes like Michael Wilmington of the Los Angeles Times, who wrote, "There's a moral charge to the action, but it's also swooningly exciting, coldly scary." Every friend might be an adversary, and every innocent person could be a traitor."

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Milk (2008)

Penn received his second Academy Award for Best Leading Actor for his depiction of real-life civil rights activist Harvey Milk, the first openly homosexual elected official in San Francisco.

 Milk, directed by Gus Van Sant, depicts Harvey's emotional and professional struggles in establishing America's first homosexual political organization. Harvey was elected to the San Francisco Board of Supervisors in 1978 while balancing his relationship with campaign manager Scott Smith.

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Dead Man Walking (1995) 

Penn is nominated for an Academy Award for his performance as convicted death row killer Matthew Poncelet in Dead Man Walking, which is based on a real incident. Susan Sarandon, his on-screen companion, went on to win the gold statuette!

The plot revolves around Sister Helen Prejean (Sarandon), a kind nun who counsels Matthew in the days leading up to his execution. They rush to get a stay of execution as Sister Prejean helps Matthew uncover his tormented soul.

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Bad Boys (1982)

Penn had his own disciplinary problems to overcome in the 1982 picture of the same name, before Martin Lawrence and Will Smith were labeled as Bad Boys. Penn portrays Mick O'Brien, a disturbed young guy who is facing rehabilitation after murdering his arch-younger enemy's brother.

Mick is taken to a juvenile detention institution after being charged with vehicular manslaughter. When Mick's adversary Paco (Esai Morales) threatens to rape his fiancée (Ally Sheedy) as a form of retaliation, he must find a method to defend her from the inside out.

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The Close Range (1986)

In the critics' circle, Sean Penn had the best of times and the worst of times in 1986: August brought the widely panned Shanghai Surprise, starring our subject and his newlywed bride Madonna in one of the decade's most infamous flops, but April found him in a different and far more successful kind of family affair.

In director James Foley's grim criminal thriller At Close Range, Penn starred opposite his brother Chris as a mafia leader (a mustachioed Christopher Walken) whose return from exile upends the lives of his adult kids.

Despite its compelling story and a stellar cast, which included Mary Stuart Masterson, Kiefer Sutherland, and Crispin Glover, the film failed to make an impact at the box office, but critics praised it, calling it "a dark jewel of a drama, with first-rate performances," according to James Sanford of the Kalamazoo Gazette.

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State Of Grace (1990)

Few could have predicted that director Phil Joanou would follow up a better-than-average teen comedy (Three O'Clock High) with a well-intentioned, albeit indulgent rockumentary (U2: Rattle and Hum) which is to say that few could have predicted that he would follow up with a tense and gripping drama like 1990's State of Grace.

Grace exploited an instantly recognizable formula while transcending it thanks to outstanding acting from its leads, starring Penn as an undercover cop whose latest case tests his loyalty to his best friend (played by Gary Oldman) not to mention his affection for his friend's sister (Robin Wright).

"Wild-eyed and sporting lank, greasy hair, Oldman dominates the screen as a truly terrifying character, while Penn effectively portrays a man battling with diametrically-opposed emotions," wrote Don Groves of SBS, calling it "a superior gangland drama that deals imaginatively with the familiar themes of family, friendship, and loyalty."

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Colors (1988)

Before New Jack City and the decade of hard-hitting urban cop dramas that followed, there was Colors, a 1988 film starring Penn and Robert Duvall as a pair of LAPD officers on a mission to rid the streets of gang activity when they aren't squabbling over their differing approaches to serving and protecting the public.

There are plenty of films that start with the same basic premise, but director Dennis Hopper working from a script by Crimson Tide writer Michael Schiffer had a fantastic cast to work with, including a slew of solid supporting players (including Maria Conchita Alonso and Don Cheadle) who helped to ground what could have been an overly familiar story.

The Washington Post's Hal Hinson said, "There's tremendous joy in watching these two actors perform." "And Hopper, who is also a brilliant actor, understands what they need to thrive."

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The Tree Of Life (2011)

Nothing gets a cineaste's anticipation buzzing quite like the announcement of a new Terrence Malick picture, and because Malick is nothing if not deliberate, we had plenty of opportunities to do so while watching Tree of Life.

Originally announced in the aftermath of Malick's 2005 film The New World, it slipped through the cracks in the release schedule in 2009 and 2010, eventually debuting in May 2011-all 139 minutes of it.

Life, the product of Malick's increasingly difficult-to-contain ambition, took viewers from the dawn of life to the twenty-first century, leaving plenty of room for solid acting from Penn, Brad Pitt, and Jessica Chastain as well as hosannas from critics like Joe Morgenstern of the Wall Street Journal, who called it "Daring in concept, occasionally daffy in execution, and ultimately unforgettable."

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Mystic River (2003) 

Penn earned his first Academy Award for Best Leading Actor for his performance in Clint Eastwood's renowned crime thriller Mystic River. The plot centers on Katie Markum's unexplained murder, which is based on Dennis Lehane's book (Emmy Rossum).

Katie's father, Jimmy (Penn), is an ex-con whose closest buddy Dave (Tim Robbins) becomes the main suspect. He pursues the murderer with zeal.

Jimmy seeks assistance from a boyhood buddy, murder investigator Sean Devine (Kevin Bacon), who is assigned to the case.

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The Falcon And The Snowman (1985)

There were many Cold War dramas in the 1980s, but The Falcon and the Snowman, released in 1985, is unlike any of them.

This fact-based, John Schlesinger-directed film stars Penn as an opportunist drug dealer who is lured into selling government secrets after being approached by a defense contractor (Timothy Hutton) who becomes disillusioned after learning that the US government's overseas activities aren't always as noble as he believes.

Nick Rogers of Suite101 said, "It's an entertaining, presumably accurate recital of facts, with two excellent performances." "However, in the case of The Falcon and the Snowman, the reality we don't see onscreen may be weirder and more powerful than the historical fiction created."

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Tobey Strickland | Reiki Master. In the process of becoming a real estate mogul. Brewery aficionado. Netflix series critic who is semi-professional. Every day, I assist clients in locating their ideal dream house. After I finish my work for the day, you can find me at Crossfit, doing yoga, or meeting up with friends to listen to live music around town. I enjoy traveling regularly, whether it's relaxing on a South American beach or hiking through Asia's mountains. Now it's your turn. What are your favorite places to visit?


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