50 Sean Penn Movies & TV Shows, Ranked Best to Worst

Brad Whitewood Sr. is a criminal, who is the leader of his gang. His teenage son, Brad Jr. who is out of work, is also drawn to the life of crime, after being attracted to his father’s lifestyle. He soon joins his father’s gang, but after witnessing a murder, he is shocked and decides to quit. Brad Jr. eventually gets arrested by the police, and they try to get him to reveal evidence that will help them arrest his father.

Poncelet is awaiting execution for rape and murder of a teenage couple. As the day of his execution nears he writes to Sister Helen Prejean, hoping that she will help him with his appeal. Based on a true incident, the story focuses on Sister Prejean’s interaction with Poncelet and how she guided the arrogant and remorseless man to open admission of his crime and acceptance divine forgiveness. . 

Mick O’Brien is a 16 year old Irish hoodlum from Chicago who commits small crimes such as snatching purses, and getting into fights, although he aspires to commit bigger and more cruel things. However, he accidentally kills an eight-year old kid, after which he is sent to prison. Prison life seems to be way tougher than he expected.

Based on the eponymous novel by James Jones, The Thin Red Line is a war drama revolving around a group of soldiers fighting to capture Guadalcanal for the Allied Forces during World War II. Featuring a brilliant star cast of Sean Penn, John Travolta, George Clooney, Jim Caviezel, and more, this film focuses on American soldiers trying to capture Japanese bunkers.

After drug dealer Carlito Brigante is released early from prison thanks to an exploitation by his sleazy lawyer friend Dave Kleinfeld, he pledges to mend his ways and rekindles his romance with former girlfriend Gail. However, despite repeated attempts to avoid temptations, he is eventually dragged into his former violent lifestyle while assisting Kleinfeld against an Italian Mafia boss.

Bobby is heading to Vegas to pay off his gambling debts before the Russian mafia kills him. However, he is forced to stop in a town in Arizona, when his car breaks down. He gets caught in various problems after he meets Grace, a local resident. 

The coming-of-age story revolves around the lives of sophomores, Stacy Hamilton and Mark Ratner, and their friends, Linda and Mike. Stacy’s older brother, Brad, is also trying to figure things out after a break up while Stacy becomes pregnant. There is also Jeff Spicoli, a stoned surfer who is constantly going up against teacher Mr.Hand. 

Terry Noonan is an undercover police officer, who is targeting Frankie Flannery, a crime boss, who is also the brother of his best friend Jackie. However, soon, it seems that the mission will not be as easy for Terry as he had expected.

The Game is a psychological thriller focusing on a lonely investment banker who is gifted a voucher for a unique game by his estranged brother that ends up wreaking havoc in his life. Starring Michael Douglas and Sean Penn as the two brothers, this film sees Douglas lose all his money in this game that becomes intrinsically connected to his real life.

Sam Dawson is an intellectually disabled father raising his daughter Lucy with the help of a group of friends who also have disabilities. As Lucy grows up her intellectual superiority threatens their relationship. Things get more complicated when Lucy is placed in foster care but keeps coming back to her dad. 

Dave, a blue-collar worker who was abducted and sexually abused as a child 25 years earlier, is the prime suspect after the daughter of his neighborhood friend, ex-con Jimmy, is found dead. While their childhood friend Sean, now a homicide detective, investigating the crime, Jimmy takes law in his own hand by launching a separate investigation.

Through flashbacks, this biographical film records the career of Harvey Milk who became America's first openly gay person to be elected to public office on the San Francisco Board of Supervisors following a successful campaign led by his young partner and campaign manager Scott Smith. A year later, he is assassinated by his former conservative colleague Dan White.

After a fatal automobile accident, lives of three unrelated individuals intersect each other – a mathematics professor with a bad heart condition, a grieving mother with a reckless past, and a reformed former convict with faith in Jesus. The movie presents three simultaneous stories about the past and present of these three individuals entwined by the fateful accident. 

Emmett Ray is a famed jazz guitarist, who believes that love is a hindrance to his musical career. His views start to change after he develops affection for a shy and mute woman. However, shortly after he gains fame, he gets married to a wealthy socialite on a whim. 

This war drama film takes us to the Vietnam War, and it tells the story of Private Eriksson who must not only fight against the enemy but also his own squad leader, Sergeant Tony Meserve, when he orders the squad members to kidnap and rape a poor farm girl. 

Before Night Falls is a biographical drama film which revolves around the life and the writings of a well-known Cuban author named Reinaldo Arenas. The film spans the whole area of his life, starting from his childhood and how he embraced the Revolution and later faced persecution, to his exile and death in the United States.

Cadets at a military school receive the news that their academy will be sold to real estate developers after one year. Upset with this news, all the cadets start an uprising hoping that the school can be saved.   

Daydreamer Walter Mitty, the negative assets manager of Life magazine, finds his job at risk when the publication decides to go online. Matters complicate further when the negative 25 which is to be used for the cover of the last edition goes missing. To find Sean, the photographer, Walter steps out of his ordinary life and embarks on a real life adventurous journey around the world.

Based on real events, this crime thriller film tells the story of a furniture salesman in 1972, who comes up with a plan to kill the then-President of the US, Richard Nixon. His plan involves hi-jacking a plane to fly over the White House in order to drop a gas bomb.

The Professor and the Madman is a biographical mystery drama film which tells the story of Professor James Murray, who had become the director of an Oxford University Press project in 1879. He begins to work on the first edition of the Oxford English Dictionary, but he is surprised when he receives over 10,000 entries from a man named WC Minor, a patient confined at the Broadmoor Criminal Lunatic Asylum.

Jim and Ned are two convicts who manage to escape from prison along with a killer. They decide to head north towards the Canadian border, but they are soon mistaken for priests. They play along and take up residency at a monastery, but things get complicated when Ned falls for Molly, a local girl.  

Critically acclaimed, experimental-drama film, The Tree of Life, is based in Texas in 1950s. It explores the story of a father, a mother and three brothers, through the eyes of the youngest son Jack. He takes the viewers into his life and mind as a middle-aged adult, who is going through an existential crisis, while reminiscing his childhood struggles.

Based on two memoirs, one by Valerie Plame and the other by her diplomat husband, the film follows the life of Valerie Plame, an intelligence officer involved in several important projects. She has been able to hide her profession from the outside world until husband’s article in a popular magazine angers the White House and her identity is leaked. 

Christopher Boyce gets a job at the CIA and he gets to know the less reputable side of the American government while he is going through classified documents. As he grows disappointed, he sells the information to the Russians, in an act of defiance. His drug pusher childhood friend, Daulton Lee, becomes a middleman between Soviets and Boyce. But as a twist of fate, Lee fails to sweep his deeds under the carpet.

Colors is an action crime drama film which tells the story of an experienced cop and his hot-tempered rookie partner, who patrol the streets of Los Angeles, while attempting to keep the gang violence under control. While doing their job, both cops deal with issues such as racism.

In 1949, Mobster Mickey Cohen rules the California criminal underworld and has even police and politicians in his pocket. A secret police unit called the Gangster Squad, comprising of Sergeant John O’Mara, Sergeant Jerry Wooters, Lieutenant Coleman Harris, Conwell Keeler, Max Kennard, and Navidad Ramirez finally manages to bring him down. 

This Must be The Place is a comedy drama film, which tells the story of a former rockstar who, after his father’s death, sets out to find the Nazi war criminal, who is responsible for his father’s humiliation during the Second World War.

The Gunman is an action drama film, which tells the story of an assassin, who is forced to go into hiding after he kills the minister of mines in Congo.  Years later, when he returns to the country as a charity worker, he becomes the target of a hit squad himself.  

Based on an award-winning novel of the same name, this political drama film revolves around the life of Willie Stark, an idealistic lawyer, who becomes the governor of Louisiana. However, as he rises to power, he also finds himself involved with corruption.

When her neighbour Kiefer tries to rape her and assault her, Maureen’s husband Eddie goes berserk. He is eventually put in a psychiatric facility. Years later, he is released and he tries to redeem himself in the eyes of his now-ex wife. However, she is already married to another man.  

Silvia Broome, who grew up in South Africa, is an expert in various languages and thus works as an interpreter in the United Nations. One day, she accidentally overhears a conversation around a plan to kill the African dictator Zuwanie who is accused of genocide. Secret Service agent Keller and Woods are tasked to protect him. Keller, however has his doubts about Silvia’s claim and intention.

Eddie is a young man who is living a confused and reckless life, along with his group of friends, having equally problematic lives. They are also addicted to drugs and alcohol. Things get interesting when another friend named Artie arrives with a date.  

The Weight of Water is a mystery crime thriller drama film which tells the story of a newspaper photographer Jean who is researching a double homicide that took place in 1873, i.e. a hundred years earlier.  Things get ugly when her life becomes parallel to that of a witness who had survived the tragic event.  

What Just Happened is a comedy drama film which tells the story of Ben, a veteran Hollywood producer, who is going through a tough time, but struggles to finish his new film, while also dealing with his personal problems. Meanwhile, he is also trying to maintain a relationship with his young daughter.

This romantic drama science fiction film takes us to a dystopian future where Earth has cooled down to such an extent that it is snowing in the middle of summer. Meanwhile, the worldwide economy is on the edge of collapse. In the middle of this, John and his wife are getting a divorce. However, before signing the divorce papers, they realize that their love is worth fighting for, despite everything happening around them.

A low-paying pawn shop employee, Weslake joins in on a plan by an amateur musician Dillard, an illegal immigrant Ramon, a pimp named Broadwalk, and a homeless man named Turtle to break into the large safe in the pawn shop. But the rewards might not be what they expected. 

After a successful career in movies, comedian Pauly Shore stars in the lead role in a series where he plays the slacker son of a millionaire. However, his career begins to sink when the series turns out to be a commercial and critical failure. Soon his friends and even his girlfriend refuse to see him, and Shore is reduced to living in his mother’s attic. However, he is soon visited by the ghost of his mentor, who encourages him to fake his own death in order to boost the popularity in his films and merchandise.

Jon Krakauer’s 1996 non-fiction book - Into the Wild - is the basis of this movie. Christopher McCandless, a young graduate from Emory University, abandons the life of privilege and sets out on a cross country drive to explore the life in wilderness. He meets various people en route who all influence him in their own meaningful way.

The Indian Runner is a drama film which revolves around two brothers Frank and Joe, who have conflicting personalities. While Joe manages to become a deputy sheriff, Frank turns to crime. Joe wants to help his brother change, but Frank’s inner turmoil impacts him.

Retiring detective, Jerry Black, promises a mother to find the murderer of her young daughter. Unconvinced that it’s an open-and-shut case, Jerry buys petrol-pump, moves in that area where he discovers more cases and clues. As he grows closer to bartender Lori, her young daughter reports befriending a person nearer to suspect’s description. So now Jerry has to quickly nab the killer. 

Freddy Gale is a jeweler whose young daughter is killed by a drunk driver. When the driver is released from prison, Freddy swears to kill him and informs him that he has only three days to live.  

Based on the life of Marjane Satrapi, the animated movie follows her journey from a young girl in Iran to growing up to be a punk-loving teenage and leaving for Paris. When she returns to Iran, it has become more intolerant with religious absurdities and liberals are being executed.  

The flightless birds of the Bird Island are a happy population, except for the three outcasts – hot-tempered Red, speedy Chuck and explosive Bomb. When the mysterious green piggies arrive on their island, everyone happily welcomes them. But Red suspects that there is some covert reason behind their visit. With Chuck and Bomb, Red sets out to get to the bottom of it. 

Joel Goodson decides to cut loose with his friend Mike, after his parents go away for a trip. He ends up having sex with prostitute Lana, getting the house burgled, and crashing his father’s Porsche. He finally decides to turn the house into a brothel with Lana for a night to earn enough to pay for the repairs. 

Well-known actor Joaquin Phoenix decides to retire from the world of acting and focus on a new career as a hip-hop musician. Later he approaches Sean Combs, American rapper and record producer, hoping he will produce the record.