The Movie Waffler FLAG DAY and Sean Penn’s Best Crime Roles | The Movie Waffler

FLAG DAY and Sean Penn’s Best Crime Roles

flag day
A look at Sean Penn's roles in the crime genre.

From the high-flying world of the New York mafia, to the battlefields of Vietnam and the prisons of Louisiana, Sean Penn's filmography is packed full of hair-raising stories that deal with the dark underworld of American society.

In his latest directorial outing Flag Day, the Academy Award-winning actor also stars as the notorious, real-life counterfeiter John Vogel with his daughter Dylan Penn playing Jennifer Vogel, an investigative reporter who struggles to rise above the wreckage of her past, while reconciling the inescapable bond with her father and his life of crime.

To celebrate the release of Flag Day in UK cinemas and on digital on January 28th, we're taking a look back at some of the best crime films from across Sean Penn's career.

Casualties of War

Casualties of War (1989)
Brian De Palma’s searing wartime drama takes us into the steaming jungles of Vietnam during the height of the conflict, where we find Penn’s Sergeant Tony Meserve committing an appalling crime and believing the chaos of war will shield him from consequence.

Based on a real-life wartime atrocity, ‘the incident on hill 92’, as reported in a New Yorker article and subsequent book by journalist Daniel Lang, the film covers the kidnapping, rape and murder of Vietnamese woman Phan Thi Mao by a squad of US soldiers.

Michael J. Fox stars as Private First Class Max Eriksson (based on the real-life counterpart Robert M. Storeby), the one good soldier in the group who opposes the rest of the team in their terrible crimes, and later risks retribution in his determined effort to bring those crimes to justice.

Critically acclaimed, the film would add another hit to the already impressive resume of De Palma, following the likes of Carrie (1976), Dressed to Kill (1980) and The Untouchables (1989), but it’s the emerging talent of Penn that would really shine through with his searing performance.

Today Casualties of War often sits in the shadow of classic Vietnam War movies like Apocalypse Now and Full Metal Jacket, but for its brutal depiction of the horrors of war it’s well worth seeking out.

Carlito's Way

Carlito's Way (1993)
Having impressed in the aforementioned Casualties of War, Sean Penn would find himself once again working for director Brian De Palma and delivering another unforgettable performance, this time in the far less harrowing mafia thriller Carlito’s Way.

Having scored a major hit with Al Pacino in Scarface (1983), De Palma attempted another crime classic with Pacino playing career criminal Carlito Brigante in Carlito’s Way.

The film opens with Carlito receiving an early prison release thanks to the work of his friend and lawyer Dave Kleinfeld (Penn). Vowing to go straight, Carlito finds himself in possession of a swinging nightclub, but it doesn’t take long for trouble to rear its head in the form of wild young gangster ‘BennyBlanco from the Bronx’. With Benny determined to go into business with Carlito and refusing to take ‘no’ for an answer, and with Kleinfeld acting increasingly erratic thanks to the copious quantities of cocaine and booze he’s consuming, not to mention the sizeable amount of money he owes the mob, trouble is brewing and Carlito will need to get out of town fast if he’s to survive…

The film was based on the books of New York state Supreme Court judge Edwin Torres, who Pacino met while working out in a New York gym as he prepped for his role in Serpico (1973).

While Pacino might have been instrumental in getting the film made and the acting great tackles the leading role himself, it’s Penn that steals the show as the sleazy, drug-fueled lawyer who gets his friend into deep trouble thanks to his wild behaviour and shady dealings.

Dead Man Walking

Dead Man Walking (1995)
Tim RobbinsDead Man Walking sees Penn take on the role of Matthew Poncelet, a character based on two notorious American murderers, Elmo Patrick Sonnier and Robert Lee Willie. Opposite Penn, Susan Sarandon stars as real-life nun Sister Helen Prejean, who becomes Poncelet’s spiritual adviser after he is put on death row in a Louisiana prison for the murder of a teenage couple.

Sister Helen, a committed anti-death penalty activist, at first tries to get Poncelet’s sentence commuted to a life in prison, despite the murderer expressing no remorse and even denying his terrible crimes. But as their relationship develops through a series of prison meetings, in a powerful scene with Penn on top form, Poncelet eventually admits to the murders in the hope of achieving some redemption.

A huge critical and commercial success, Dead Man Walking was nominated for multiple Oscars including Best Actor for Penn. It was Sarandon who eventually netted an Academy Award for her role as Sister Helen. A moving and unmissable crime drama.

Mystic River

Mystic River (2003)
With Hollywood legend Clint Eastwood in the director’s chair, Penn picked up a Best Actor Academy Award for his leading role in 2003’s noirish psychological crime drama, Mystic River. It was the actor’s fourth time nominated for the award, finally scoring a win having previously been in contention for Dead Man Walking (1996), Sweet and Lowdown (2000) and I Am Sam (2002).

Mystic River opens on three Irish-American boys, Jimmy, Sean and Dave, in '70s Brooklyn, whose lives are forever changed when Dave is abducted and subjected to lengthy abuse before finally escaping. After drifting apart as adults the lives of these men become entwined once again after another tragedy when Jimmy, now an ex-con, discovers his daughter has been brutally murdered. While homicide detective Sean is on the case Jimmy does a little investigating of his own… chief on their list of suspects? Childhood friend Dave.

Written by Brian Helgeland, the Oscar winning writer of another crime classic, L.A. Confidential, this powerfully dark and gritty film finds Penn flanked by a team of equally talented actors including Tim Robbins, Kevin Bacon, Laurence Fishburne and Laura Linney.

One of his most celebrated roles, Mystic River is essential viewing for Penn’s nuanced character work.

Gangster Squad

Gangster Squad (2013)
Sean Penn unleashes a crimewave on Los Angeles as vicious real-life mobster Mickey Cohen, in Gangster Squad. Set in 1949, Ruben Fleischer's action crime romp is based on the true story of the ‘Gangster Squad’, an elite division of the LAPD tasked with combatting organised crime.

When Penn’s Cohen decides to expand his organisation to cover the entire West Coast, a secret group of incorruptible police officers is assembled by Sgt Jack O’Mara (Nick Nolte) to fight the expansion… by any means necessary!

Cue gunfights aplenty and a barrage of action set-pieces as the squad takes the battle to Cohen’s gang. Although the film is heavy on the car chases and explosions, in actuality the Gangster Squad was much more focussed on intelligence gathering and rooting out police corruption, however, the real-life O’Mara has noted that the squad certainly did many things that would be considered illegal today.

Penn’s Flag Day co-star Josh Brolin, Michael Peña, Ryan Gosling and Anthony Mackie comprise the film’s star studded crime fighting unit, with Emma Stone appearing as Penn’s femme fatale lover.

For a fun organised crime tale with plenty of action and a killer cast, look no further than Gangster Squad.

Flag Day is in UK cinemas and on digital 28 January from Vertigo Releasing.