Undoubtedly one of the best actors of his generation,Sean Pennhas become a staple of drama that can truly elevate films above what could already be high expectations. He’s a force of nature whose presence feels invasive in every movie or TV show he appears in, and the depth he gives to his characters is enough to give inject mystery and make the audience interested. With him, it’s not just about screenwriting. There’s always something more than only his range can provide.
His career goes way back. All the way to 1982, whenPenn played Jeff Spicoliin Amy Heckerling’sFast Times at Ridgemont Highwith so much ease and persona that, although it was only a coming-of-age comedy, he made heads turn. His breakout role in one of the most popular comedies of the ’80s made Hollywood know there was a new kid in town.
What came after was controversial: the marriage to Madonna and his meta approach to performing inThe Falcon and the Snowman. When the ’90s arrived, Penn was already tired and actually drifted away. It doesn’t mean his career ended.
Activism, political views, and his foreign policy are also part of Penn’s agenda that unfortunately crosses over to his acting career sometimes. But regardless, today we invite you to celebrate one of Hollywood’s greatest actors who’s also a difficult figure in the media spotlight. These are the best films by Sean Penn, according to critics at Rotten Tomatoes.
10Casualties of War (1989) - 83%
Casualties of Warby Brian de Palma realistically portrayed the events of the incident on Hill 192 during the Vietnam War, when a Vietnamese woman was kidnapped, sexually assaulted, and murdered by American soldiers.
Related:Best Vietnam War Movies, Ranked
Penn gives life to Sergeant Meserve, the man in charge of the squad that would end up being accused and convicted of the crime. Penn acts against a great cast ensemble that includes Michael J. Fox, John Leguizamo, John C. Reilly, and Ving Rhames.
9The Tree of Life (2011) - 85%
In Terrence Malick’s heavily discussed film,The Tree of Life, Penn plays the older Jack O’Brien, an executive whose past is part of the film’s journey and the reason why he’s gone through an emotional crisis. Malick’s film was deemed hard to digest, but it was only because the film sought something else than just an honest and beautiful portrayal of human evolution in the modern age. Penn’s role is outstanding, andThe Tree of Lifeis much better than people said it was more than 10 years ago.
8State of Grace (1990) - 85%
State of Graceis a very underrated crime thriller that changed Penn’s game for the best. It was his first role playing an adult character, with everything it brings. It told the story of Terry Noonan (Penn), an undercover cop who infiltrates a gang of criminals in Hell’s Kitchen.
Noonan’s close friend from the past is played by none other than Gary Oldman. Sadly, the appraisal of critics didn’t do more for this cult film that not many people have seen.
7At Close Range (1986) - 86%
Penn plays Brad Whitewood Jr. inAt Close Range, a crime drama that tells the true story of a criminal gang led by Brad Whitewood Sr. (Christopher Walken), who collides heavily, but ultimately connects, with his son’s attitude in seeing crime as a way of life. This a veryunderrated dramatic thrillerof the ’80s that featured an already notable young actor who had the capacity to steal scenes on his behalf.
6Mystic River (2003) - 89%
Clint Eastwood’s filmMystic Rivertook us to the suburbs of Boston, where a horrific crime has just taken place. It’s not only the victim but who her father is. Jimmy Markum (Penn) is a mafia boss whose power lies dormant until it’s time to indulge in some revenge.
Unfortunately, all clues point to one of Markum’s friends from his childhood. Everyone who saw the film in 2003 automatically saidPenn would get an Academy Awardfor his performance, and of course, he did.
5This So-Called Disaster (2003) - 90%
Do you want to get a lesson in acting? SeekThis So-Called Disasterfor a quick journey through the insides of a stage production featuring performance behemoths preparing for the play. Penn is one of those actors featured in the documentary that also stars Sam Nick Nolte and Sam Shepard as he prepares himself and the others for his playThe Late Henry Moss.
4Licorice Pizza (2021) - 90%
In Paul Thomas Anderson’sLicorice Pizza, a veteran Penn plays a veteran actor in this portrayal of social dynamics in the San Fernando Valley 40 years ago. Jack Holden (actually based on real actor William Holden) is flirty with Alana, the young actress who wants to audition for his next film in the ’70s.
Related:Nicholas Hoult’s 10 Best Movies, Ranked by Rotten Tomatoes
Ultimately, Holden intends to prove his worth by performing a stunt with Alana who gets hurt in the process, making the film’s lead Gary appear out of nowhere to take care of her.
Bad Boyswas Rick Rosenthal’s next directing gigafterHalloween II. Fortunately, he changed genres. The film tells the story of Mick (Penn), a young thug whose way of life consists of misbehaving in the slums of Chicago. After a gang fight goes really bad, Mick commits a murder, for which he gets sent to a detention center where he will face the burden of his acts.
2Milk (2008) - 83%
Penn’s second Oscar as Best Actor would be given to him after his performance in the biopicMilk. In the film, he portrayed Harvey Milk, the gay rights activist and politician who became the first openly gay man to be elected in California for public office. It’s very hard to find another performance by the actor that seems as tailor-made for him as this one.
Penn’s performance as Matthew Poncelet inDead Man Walkingis undoubtedly the best of his career. In the film, Penn plays a convict waiting to be executed for a horrible crime who during his last days on death row, connects emotionally with a nun offering support to people on death row.
He stars alongside Susan Sarandon, who plays Sister Helen Prejean in the film. Her role is a riveting depiction of unconditional love without the romantic element.
