The Town, Ben Affleck’s crime saga from the Boston area, turns ten this year. Our 14 other recommended films for those who liked this Irish-American crime-drama classic have been selected in honor of its theatrical release. All of these films have strong thematic and stylistic ties, which can be grouped together under the broad umbrella terms of “heist” or “crime movie,” regardless of whether they are set in Boston or not. I’ll get right to it now.
1. Point Break
Point Break, starring Keanu Reeves as FBI rookie Johnny Utah who goes undercover among a group of surfers suspected of a series of bank robberies in Southern California, is easily one of the most quotable and hilariously overacted movies of the ’90s. Utah is captivated by Bodhi, the de facto leader of the surf crew, who espouses and practices a pseudo-philosophy played with unbridled enthusiasm by Patrick Swayze. For Kathryn Bigelow, this was one of her debut films as a director who excels at fast-paced action, tense set pieces with a lot of stunt work, and male archetypes who can’t get enough of the next thrill, no matter how dangerous it may be.
We’ll move on to one of the decade’s most influential and well-known films with Next. If you’ve seen The Town and are a fan of crime dramas and heist films, you’ve probably seen Heat a few times already. One of the most notable things about this film is how influential it has been in film and television to this day (has any one scene, the botched bank heist, been more frequently referenced in staging shoot-out sequences?). Nothing about this film has aged, and it still has the same sense of excitement, thrill, and groundbreakingness that it did when it was released 25 years ago.
If there were any redeeming qualities to this film, it would be that Al Pacino played LAPD Detective Vincent Hanna, who pursues Robert De Niro’s master thief Neil McCauly. As directed by crime-movie auteur Michael Mann, however, this blatantly by-the-book tale of cops and crooks transforms into a sprawling, austere, high-octane — yet deeply intimate, moody and atmospheric —picture about people’s interconnectedness and the psychological effects of their choices in life. Despite being on opposite sides of the law, these two men are bound together by an intangible force that can only be described as mutual respect.
3. L.A. Confidential
The next item on our wish list is a vintage 90s piece. L.A. Confidential takes an episodic look at crime in Los Angeles in the mid-1950s, focusing on the intersections of law enforcement, the criminal justice system, celebrity culture, and the media. Curtis Hanson tells a tangled tale of corruption, lust, and violence, all set against the backdrop of the American media-industrial complex’s growing interest in true crime and police work.
It begins with Edmund Exley (Guy Pearce), a well-dressed LAPD sergeant who agrees to testify against his fellow officers in exchange for a promotion. As a result, he’s at odds with his colleagues, particularly tough-as-nails cop Bud White (Russel Crowe). Kim Bassinger’s Lynn Bracken, a high-end prostitute and possible key witness in a mysterious café massacre in which White’s ex-partner has been murdered, becomes involved with White later in the film.
A smarmy drug officer played by Kevin Spacey, Sergeant Jack Vincennes, works for TV networks and tabloid magazines as an insider, framing and busting high-profile public figures involved in scandalous acts of behavior. As a result of this, the film, based on a James Ellroy novel, delivers a taut, tightly wound noir thriller that delves into the seedy underbelly of 1950s Los Angeles.
4. Mystic River
As we enter the new millennium, we have Clint Eastwood’s Mystic River as our first selection. This is one of the most depressing films of the century so far, dealing with issues such as childhood trauma, sexual abuse, murder, betrayal, and vengeance as well as other dark themes.
A car pulls up with two men in it and steals Dave away from Jimmy, Sean, and Dave, three childhood friends from Boston. Some time later, Dave (perfectly played by Tim Robbins as an insular, fractured man) learns that he was sexually abused by the men who kidnapped him and struggles with his trauma when he is implicated in the death of Jimmy’s teenage daughter Katie. As a former con, Jimmy (Sean Penn) is now a detective with the Massachusetts State Police and is pursuing his own investigation into the murder while Sean (Kevin Bacon) closes in on the truth.
Because of this, Clint Eastwood chose a cold, ominous color scheme, with muted blue-gray tones and hard shadowy night exteriors, to go with the film’s somber subject matter. This film solidified Clint’s position as one of the world’s leading filmmakers and demonstrated that he was a studio-filmmaker who was not afraid to delve into the more sinister aspects of human nature.
5. Layer Cake
Layer Cake, Matthew Vaughn’s spirited take on the British gangster film, is the next entry in the series. Before making his directorial debut, Vaughn worked as a producer on Guy Ritchie’s blockbusters Lock, Stock and Two Smoking Barrels and Snatch.
A slightly more polished and less tongue in cheek action-crime movie set in London, Vaughn proved himself as a worthy successor to Guy Ritchie’s hyper-kinetic comedic rough and tumble style with Layer Cake. As an unnamed cocaine trafficker who runs a tight ship and avoids getting involved in the dirty business, Daniel Craig, in his first major leading role, plays a stern figure. His boss, Jimmy, summons him just as he’s about to leave for retirement and tells him he must oversee the sale of one million ecstasy tablets from a lowlife criminal, which he soon discovers had stolen the ecstasy from a gang of Serbian war criminals. This is where we find him.
He must also look for Jimmy’s daughter’s drug-addicted friend Charlie, who has gone missing. With no choice but to comply, Craig’s character finds himself slipping deeper and deeper into the drug business he had spent his entire career trying to avoid. The film relies on effective storytelling, witty dialogue, brutal violence, and a breakout performance from a young Daniel Craig before he became James Bond to make it a success.
6. The Departed
The Departed, the next film in our lineup, is one of Scorsese’s finest works in his illustrious filmography, and it pairs beautifully with The Town. The film is an absolute masterclass in big-budget, star-powered gangster movies, regardless of the chorus of people who dispute the Oscars for awarding Scorsese the Best Directing statue as a belated cop-out for previous oversights (*ahem* Goodfellas *ahem*).
When it comes to actors, Jack Nicholson’s performance as Irish mob boss Frank Costello in this film will go down as one of the most memorable in film history. In addition to cooperating with the Boston police, Costello has a mole in Colin Sullivan (Matt Damon), and an informant in the form of Billy Costigan (Leonardo DiCaprio) is slowly working his way up the ranks of Costello’s organization.
Costigan grows increasingly suspicious that the police have their own double-crossing agent as Costello grows increasingly convinced that his gang has a mole. As a result, Sullivan is urged by Costigan to go after the mole. Aside from the film’s dual narrative structure (inspired by the acclaimed Hong Kong film Internal Affairs), the performances by the A-list cast, who collectively exude Boston grit and wit with such panache, make this the definitive Boston crime-drama. It’s the best in the genre.
7. Inside Man
The next film on our list is Spike Lee’s opulent heist film. This film is a great match for The Town because it’s fast-paced and lighter in tone, but it’s no less powerful or energizing for it. While still at the height of his powers, Spike expertly weaves together disparate themes and storylines into a single work of mainstream entertainment that works as a whole.
While it is inspired by classic bank heist films like Dog Day Afternoon, it differs from those classics in that it is told primarily from the point of view of the police, in this case NYPD hostage negotiator Keith Frazier, played by Denzel Washington with suave confidence. Clive Owen’s mysterious and cunning Dalton Russell leads a band of bank robbery perpetrators as they hold up and kidnap the employees of a Manhattan bank owned by Arthur Case (Christopher Plummer), a tyrannical, stoic man who is doing everything in his power to hide a shady past.
Even though the film is always one step ahead of the audience, it accomplishes the nearly impossible by providing all of these things while also incorporating a high stakes moral quandary at its core, all without ever seeming to exert much effort.
8. Lucky Number Slevin
Often overshadowed by other slick-talking, fast-paced crime films such as Pulp Fiction, Snatch, or The Departed but no less worthy of your attention if you are a true crime movie enthusiast, Paul McGuigan’s underrated gem from 2006 (what a year!).
Early-mid 2000s, Josh Hartnett showed promise as a major Hollywood leading actor, and it’s a shame he never fully capitalized on this (hopefully things will change as he’s scheduled to appear in two major upcoming productions, most importantly Guy Ritchie’s next effort, Wrath of God). Hartnett embodied a rare trifecta of effortless poise, charm, and charisma as the title character Slevin. Slevin is mistaken for his missing friend Nick by a couple of henchmen working for The Boss (Morgan Freeman), who, upon discovering him in Nick’s empty apartment, tell him he must repay a massive gambling debt.
Alternatively, if Slevin agrees to kill the son of The Rabbi’s rival, The Boss (Ben Kingsley), who he believes murdered his son, he will be relieved of his debt. The Rabbi’s henchman kidnaps Slevin after he is freed and demands a large gambling debt from him. After that, you’re treated to a well-crafted, tightly scripted thriller featuring big-name movie stars perfectly cast in their roles, as well as a few surprises that will keep you guessing until the very end.
9. Gone Baby Gone
Gone Baby Gone, directed by Ben Affleck in his directorial debut, comes next. Adapted from Dennis Lehane’s book of the same name, which was the inspiration for the Mystic River novel on which the film was based, this classic Boston crime-drama is a similarly depressing, unforgiving mystery thriller/portrait of people going through a crisis.
A three-year-old girl goes missing, and Private Investigators Patrick (Casey Affleck, Ben’s brother) and Angie (Michelle Monaghan), Patrick’s partner/lover, are hired to find her. This film features Amy Ryan as Helene, the mother of the young girl. Helene is a drug addict who gets into some shady business dealings with her supplier. Amy Ryan was nominated for an Oscar for her performance.
Much like in Mystic River, the plot takes you down one path before delivering a complete and total 180 degree turn. As a result, the film portrays people who are at a crossroads in their lives who are trying to do the right thing despite their morally ambiguous situation.
Takers, which came out the same year as The Town, takes the top spot on our list for the year 2010. While The Town focuses on urban Boston grit, Takers is a swanky Los Angeles heist film with high-wire set pieces and a lot of explosions, shootouts, and chase sequences that will appeal to fans of glitzier heist films.
A former member of Gordon Cozier’s crew, Ghost (rapper T.I. ), proposes a job that would set them all up for life: robbing an armored car carrying $12 million to the seasoned professional Gordon Cozier (Idris Elba). Cops Jack Welles (Matt Dillon) and Eddie Hatcher (Eddie Hayes) are hot on their trail (Jay Hernandez). As the heist unfolds and the cops narrow in on the suspect, it becomes apparent that Ghost’s motivations for the heist may not be what they seem. It’s great if you’re looking for some standard Hollywood action fare that’s exciting and easy to digest.
11. Killing Them Softly
The Assassination of Jesse James by the Coward Robert Ford, in which director Andrew Dominik reunited with Brad Pitt after his critically acclaimed but little-known masterpiece, is next on the list. A modern story about American idealism running its course replaces the old-fashioned setting and mythos of the American frontier.
During a mob-run illegal poker game in Boston, Pitt plays Jackie Cogan, a jaded hitman who is unusually talkative. He is hired to find three low-level crooks who stage a robbery. A New York hitman, Mickey (James Gandolfini), has become a shell of his former self while serving parole and has taken up a life of heavy drinking and indulging in prostitutes before helping him find the three fugitives in Florida.
Taken from crime novelist George V Higgin’s 1974 novel Cogan’s Trade, this film is an ironic, violently chaotic cautionary tale set against the backdrop of a financial crisis in America, while simultaneously believing that a new beginning is just around the corner thanks to Barack Obama’s election. The film follows two hitmen, whose cynicism and disillusionment only grow as the story progresses.
12. The Drop
Dennis Lehane, the poet laureate of Boston’s crime fiction, makes his screenwriting debut with Animal Rescue, an adaptation of one of his short stories from 2009 that shifts the action from Lehane’s native Boston to Brooklyn. In The Drop, blue-collar workers become entangled in the criminal underworld of mobsters and murderers through no fault of their own.
A quiet, soft-spoken bartender named Bob Saginowski (Tom Hardy) works at a dive bar in Brooklyn for his cousin Marv (James Gandolfini) and has a mysterious past. It was a long time ago that Marv handed over ownership of his bar to the Chechen mafia family that now uses it as “the drop”—a safe-house for illegal money to be collected—for their own benefit. Two masked assailants rob the bar they’re working at one night while they’re both drunk, and the Chechen mobsters threaten to hold them accountable if they don’t pay up. This is a well-made thriller with a surprising amount of heart and warmth hidden underneath all of the grit and machismo. Aside from that, it serves as a fitting sendoff for Gandolfini’s brilliant career, as this was his final performance before retiring.
13. Hell or High Water
The next film is David Mackenzie’s Hell or High Water, set in a Texan town scorched by the summer sun. What could have been a blatant copy of No Country for Old Men ended up being a surprise sleeper hit and one of the year’s best films.
Ben Foster and Chris Pine star as a pair of bank robbers from Texas’ Panhandle: Toby and Tanner. After their mother passed away from illness and the debt she took on for the ranch property through a reverse mortgage, they only target Texas Midlands Bank branches when they commit robberies.
Marcus Hamilton, an aging Texas Ranger (played to perfection by Jeff Bridges), and his close friend Alberto Parker are hot on their trail (played by underrated character actor Gil Birmingham). Despite the film’s reliance on standard Western tropes, it breathes new life into the genre thanks to its tight pacing, compelling characters, and elegiac, melancholy tone. It’s well worth seeing.
We’ll end with Widows, Steve McQueen’s all-female heist film that no one saw coming. Best-selling author Gillian Flynn wrote the screenplay, Academy Award-winning director Steve McQueen directed the film, and an all-star cast of established actors as well as newcomers played the lead roles, ensuring the movie would be a worldwide hit. The film succeeds in almost every other way despite its disappointing box office performance.
Harry Rawlings (Liam Neeson) and his crew are gunned down by police after they attempt a $2 million bank robbery that goes horribly wrong. After the incident, Harry’s widow, Veronica (Viola Davis), receives a threatening visit from crime boss Jamal (Brian Tyree Henry), who has his sights set on a Southside Chicago political campaign.
Veronica recruits two other widows from Harry’s crew, Linda (Michelle Rodriguez) and Alice (Elizabeth Debicki), along with Linda’s babysitter Bell (Cynthia Erivo), to carry out the heist themselves after discovering a set of detailed instructions laid out by her husband to rob the home of racist politician Tom Mulligan (Robert Duvall), whose son Jake Mulligan (Colin Farrell) is running against Jamal in the municipal race. It’s clear that McQueen cares about more than just getting rich off of this one job.
He gives us a glimpse of life in southside Chicago and the racial disparities that give rise to characters like Jamal and Jatemme (Daniel Kaluuya). Rather than focusing on a heist for the sake of money or power, this film explores how a heist can help these women reclaim their identity and integrity, abandoning one of the genre’s common tropes in the process.