The movies have always had a way of making the life of an outlaw look fun. The secret is as easy as defying tradition by making the “bad guy” the protagonist of the story, or even taking innocents out of the equation completely. These classic films will force you to reconsider your moral standards.
The Godfather (1972)
In addition to being one of the best films about the “family business,” Francis Ford Coppola‘s Best Picture Oscar-winning adaptation of Mario Puzo’s The Godfather is a genuine family story all the way to its core, albeit a violent one. It follows Michael Corleone (Al Pacino), who is motivated by the attempted murder of his mob boss father, Don Vito (Marlon Brando), to take matters into his own hands, leading him down a path to become one of the most feared leaders in the world of organized crime.
Psycho (1960)
The true antagonist of Alfred Hitchcock’s seminal horror movie classic, Psycho, is unquestionably Anthony Perkins’ Norman Bates. However, what leads Marion Crane (Janet Leigh) to make a fateful stop at the Bates Motel is her decision to go on the run with stolen money.
The Talented Mr. Ripley (1999)
The title character of The Talented Mr. Ripley, Anthony Minghella’s acclaimed adaptation of Patricia Highsmith’s 1955 novel, is a conniving con artist. However, much like most of the people Matt Damon‘s Tom Ripley encounters, it is hard not to fall for his charms.
Pulp Fiction (1994)
There really are not any “good guys” in Pulp Fiction, or in most of Quentin Tarantino’s movies, for that matter. However, there are certainly some characters in the dazzling crime thriller that audiences have more affection for than others, especially Vincent Vega (John Travolta) and Jules Winnfield (Samuel L. Jackson), who have to be the two most down-to-earth mob hitmen in pop culture history.
Batman Begins (2005)
I have never admired a character in my life more than DC Comics’ Dark Knight, but even I will be the first to call out Bruce Wayne for who he really is: a vigilante, which makes his crusade for justice in Gotham illegal. One of the few live-action Batman movies to address this moral gray area is Christopher Nolan‘s Batman Begins, in which James Gordon (Gary Oldman) is the only cop willing to support the Caped Crusader (played by Christian Bale), but even he has his doubts.
Goodfellas (1990)
The flashbacks to Henry Hill’s youth at the beginning of Martin Scorsese‘s Goodfellas establish a life in the mafia as a childhood aspiration for him. Thus, you almost cannot help but feel proud of Ray Liotta’s character as he rises up in the ranks of the criminal underworld and disappointed when the law knocks him down a peg.
Dog Day Afternoon (1975)
Director Sidney Lumet’s Dog Day Afternoon is a crime thriller based on an incredible true story starring Al Pacino as an amateur crook whose simple bank robbery plans evolve into a challenging hostage situation. Just like John Wojtowicz, the real person who inspired the film’s main character, Sonny Wortzik, his only reason for committing the crime is to afford his lover’s transgender operation, which I can empathize with.
Catch Me If You Can (2002)
Steven Spielberg‘s acclaimed 2000s-era movie, Catch Me If You Can, is based on the alleged true story of Frank Abagnale Jr., who passed himself off as an expert in multiple fields while living off fraudulent checks while he was barely beyond his teenage years. The casting of Leonardo DiCaprio as the clever crook immediately earns our sympathies, putting Tom Hanks in the rare position of playing the default antagonist as Carl Hanratty, an FBI agent trailing Frank.
Heat (1995)
Michael Mann‘s powerful thriller, Heat, is defined by its moral ambiguity, portraying the story of a group of professional bank robbers tailed by the LAPD from both sides of the law. By the end, it is hard not to feel bad for expert thief Neil McCauley (Robert De Niro) when he is finally cornered by Lieutenant Vincent Hanna (Al Pacino).
Ocean’s Eleven (2001)
George Clooney’s recently released convict Daniel Ocean rounds up a gang of 10 other professionals to rob three Las Vegas casinos at once in director Steven Soderbergh’s remake of Ocean’s Eleven. The acclaimed heist flick makes it easy for the audience to side with these thieves, not just by making them all funny and likable, but also by making their target, Terry Benedict (Andy Garcia), quite despicable.
Inception (2010)
Amid its ingenious concept (taking place in a world where dreams can be experienced on demand with revolutionary technology) and breathtaking visuals, it is often easy to forget that Christopher Nolan’s Inception is, essentially, a heist movie. Dom Cobb (Leonardo DiCaprio) and his crew specialize in stealing valuable information from unsuspecting targets directly from their minds (or planting an idea in their heads) by kidnapping them and infiltrating their subconscious, which is a terrifying thought.
Escape From New York (1981)
When we first meet war veteran Snake Plissken (Kurt Russell) in John Carpenter’s Escape from New York, he has already been sentenced to the penal colony that used to be Manhattan for robbing the Bank of the Federal Reserve. This convinces the United States Police Force that he is the perfect choice to infiltrate the urban dystopian nightmare to rescue the president (played by Donald Pleasence) in exchange for his freedom.
Nightcrawler (2014)
I once saw an interview with Jake Gyllenhaal and Nightcrawler‘s writer and director, Dan Gilroy, in which they describe the film as “a success story.” While Gyllenhaal’s aspiring independent news videographer, Louis Bloom, is not afraid to put his ethics on the back burner and flat out break the law to get the juiciest and bloodiest scoops possible, I cannot help but agree.
John Wick (2014)
The world seems to love professional assassins (fictional ones, at least), and few are more lovable than Keanu Reeves’ title “hero” from the revenge movie favorite, John Wick, and its sequels. Of course, who wouldn’t empathize with a recently widowed man whose new dog was murdered in cold blood by a crew of young punks who also stole his car?
Guardians Of The Galaxy (2014)
One of the Marvel Cinematic Universe’s most unexpected hits is the story of a group of unlikely heroes who come to be known as the Guardians of the Galaxy. James Gunn’s hilarious, heartfelt, and action-packed breath of fresh air stars Chris Pratt, Zoe Saldaña, Dave Bautista, Vin Diesel, and Bradley Cooper as a group of cosmic outlaws who flee prison together and manage to redeem themselves by risking their lives to take down an oppressive tyrant (played by Lee Pace).
The Wolf Of Wall Street (2013)
Based on the memoir by Jordan Belfort, director Martin Scorsese’s The Wolf of Wall Street should be seen as nothing more than a cautionary tale. However, Leonardo DiCaprio’s charming, Oscar-nominated performance as the stockbroker-turned-motivational speaker almost makes you want to see him succeed despite his despicable habits and corrupt aspirations.
Kill Bill (2003-2004)
In Quentin Tarantino’s two-part action saga, Kill Bill, Uma Thurman’s The Bride wanted to put her reputation as the deadliest woman in the world behind her when she got pregnant and decided to settle down. Unfortunately, her former employer, Bill (David Carradine), and colleagues from the Deadly Viper Assassination Squad put her in a coma and, seemingly, murdered her unborn daughter, which makes her “roaring rampage of revenge” feel justified.
Looper (2012)
Rian Johnson’s inventive, sci-fi twist on the film noir movie genre, Looper, takes place in the future, but still mere decades before time travel has been invented. Joseph Gordon-Levitt stars as Joe, who is hired to kill and dispose of people sent back to his time by the mob, but his career trajectory changes when his latest target turns out to be his older self (played by Bruce Willis).
Joker (2019)
It might be a bit of a stretch to call Todd Phillips’ Joker a film that coerces you into rooting for its unlawful protagonist, because I have absolutely no sympathy for any of the terrifying acts that Arthur Fleck commits. Then again, with much credit to Joaquin Phoenix’s devastating, Oscar-winning performance, it is hard not to feel bad for the man, given his harsh life circumstances and struggles with mental health, even if he is destined to cause Gotham City a lot of pain someday.
Don’t Breathe (2016)
At the start of Fede Alvarez’s intense thriller Don’t Breathe, you are not sure who to root for, as our protagonists (played by Jane Levy, Dylan Minette, and Daniel Zovatto) are seen breaking into the home of a non-seeing war veteran (played by Stephen Lang), intending to steal from him. However, it becomes easy to fear for these thieves when the owner of the house begins to violently retaliate and more terrifying secrets about him come to light.
Road To Perdition (2002)
Director Sam Mendes’ adaptation of the acclaimed graphic novel, Road to Perdition, stars Tom Hanks as a mob enforcer who must protect his young son (played by Tyler Hoechlin) after he witnesses a murder in 1930s Illinois.
Ant-Man (2015)
Instead of the original Ant-Man, Dr. Hank Pym (Michael Douglas), the Marvel Cinematic Universe made formerly incarcerated felon Scott Lang (Paul Rudd) the star of its adaptation of the Marvel comic. After his criminal record costs him his Baskin-Robbins job, he is drawn back into crime and steals what turns out to be a special shrink suit, which is how he gets roped into the most important burglary of his life by Dr. Pym.
Sin City (2005)
I like to think of Det. John Hartigan (Bruce Willis) is the main hero of Robert Rodriguez and Frank Miller’s Sin City, but Mickey Rourke nearly steals the show in a segment called “The Hard Goodbye.” The story follows Marv, an ex-convict who returns to his violent ways to duke out some vigilante justice and avenge the murder of a woman who suddenly died after spending a night with him.
Dead Presidents (1995)
Dead Presidents is a must-watch ’90s movie centered on a Black character, namely Larenz Tate as Anthony Curtis, who is a Vietnam vet forced to turn to crime to support his family.
Public Enemies (2010)
Casting Johnny Depp, who was one of the most bankable and beloved movie stars in Hollywood in the late 2000s, as John Dillinger in Michael Mann’s Public Enemies was a stroke of genius to get the audience immediately on the side of the notorious bank robber.
Hard Candy (2005)
In Hard Candy, Elliot Page plays a teenager named Hayley who is seemingly lured into a trap by a child predator named Jeff (Patrick Wilson). However, we, and Jeff, come to discover that he is really Hayley’s prey when he is subjected to the teenager’s torturous acts.
Dom Hemingway (2013)
Jude Law stars in writer and director Richard Shepard’s Dom Hemingway in the title role of a former safecracker who is released from a years-long prison sentence and returns to London looking to collect what he believes he is owed.
Cruella (2021)
Who knew that Disney could make audiences empathize with an attempted puppy murderer? Indeed, they achieve this with Cruella by casting Academy Award winner Emma Stone in the title role, who is portrayed as a tragic figure forced to become a pickpocket as a child after her mother’s sudden murder.
Take The Money And Run (1969)
Co-writer and director Woody Allen stars in the mockumentary Take the Money and Run as Virgil Starkwell, who is so inept, yet so affable, that you cannot help but hope to see him make a killing as a bank robber.
Trap (2024)
Josh Hartnett leads M. Night Shyamalan’s Trap as Cooper, a father who takes his teenage daughter to a concert, which he discovers is being used as an elaborate plan to catch a notorious serial killer. This turns out to be a great concern for Cooper because this criminal, known as “The Butcher,” is none other than him.
Burglar (1987)
Whoopi Goldberg stars in Burglar as Bernice, a non-violent thief who wrongfully becomes the prime suspect in a murder investigation when her latest target, the ex-husband of a dentist who just wants her jewelry back, suddenly turns up dead.
Now You See Me (2013)
The main characters of Now You See Me (played by Jesse Eisenberg, Woody Harrelson, Isla Fisher, and Dave Franco) are a team of magicians who use their skills in illusion to pull off heists and pass off their loot to people in need, like Robin Hood with a few extra tricks up their sleeves.