This year marks the 10th anniversary of Ben Affleck’s Boston crime-opus The Town. In honor of its release, we bring you 14 other movies that you should add to your watchlist if you enjoyed this iconic addition to the Irish-American crime-drama. While not all these movies are centered around Bostonians, or even take place there, they all share strong thematic and stylistic ties that can be grouped under the loose umbrella terms of “heist” or “crime movie”. Now, without further ado:
1. Point Break
Easily one of the most quotable and hilariously over-acted movies of the ‘90s, Point Break stars Keanu Reeves as FBI rookie Johnny Utah, who goes undercover amongst a group of surfers suspected of a series of bank robberies in Southern California. Utah finds himself enthralled by the pseudo-philosophy espoused and practiced by the surf-crew’s de facto leader, Bodhi, played with irrepressible glee by Patrick Swayze. This is one of Kathryn Bigelow’s earliest showcases as a master of fast-paced action, tense, stunt-heavy set-pieces, and slightly insufferable yet compelling male archetypes who are constantly searching for the next thrill, no matter how dangerous it may be.
Next up, we have one of the most influential and iconic movies of the ‘90s. If you’ve seen The Town and are serious about crime-thrillers and heist movies, it’s almost certain you’ve already seen Heat a handful of times. But this film is truly one-of-a-kind, namely because even to this day, its influence is felt in a vast number of movies and TV shows (has any one sequence—the botched bank heist—been referenced more in staging shoot-out sequences?). Absolutely nothing in this film has lost any of its fundamental power; it feels as fresh, thrilling, and ground-breaking as it did 25 years ago.
Perhaps its biggest selling point would be that it served as the first time two of Hollywood’s most decorated leading men went toe-to-toe on-screen, as Robert De Niro, who plays master thief Neil McCauly, is chased by LAPD Detective Vincent Hanna, played by Al Pacino. In the hands of crime-movie auteur, Michael Mann, however, this seemingly by-the-books cops-and-robbers tale transforms into a sprawling, austere, high-octane—yet disarmingly intimate, moody, and atmospheric—movie about the interconnectedness of people and the psychological consequences their life-choices have on one another. The core of the film resides in these two men who, despite occupying different sides of the law, find themselves tethered by some intangible force, which can only really be defined as mutual respect.
3. L.A. Confidential
Next on our list is a classic period-piece from the ‘90s. L.A. Confidential is an episodic look at crime in mid-century Los Angeles—and namely, the intersecting avenues of police, crime, celebrity culture, and the media that were beginning to take shape. Working with a masterful script, Curtis Hanson delivers a knotty tale of corruption, lust, violence, and the burgeoning of the American media-industrial-complex’s obsession with true crime and police work.
The film picks up with clean-cut LAPD sergeant Edmund Exley (Guy Pearce), agreeing to testify against his fellow cops (who have been hit with a case of police brutality) in exchange for a promotion. This puts him directly at odds with his department and especially hard-nosed, roughhouse cop Bud White (Russel Crowe). White later develops a relationship with Kim Bassinger’s Lynn Bracken, a high-end prostitute and potential key witness in a mysterious café massacre, which has left White’s ex-partner murdered. Opposite them is Kevin Spacey’s smarmy sergeant Jack Vincennes, a narcotics officer who serves as an insider for TV networks and tabloid magazines to frame and bust high-profile public figures engaging in scandalous acts. Based on a James Ellroy novel, the film balances these multiple storylines in mesmerizing fashion, delivering a tense, tightly wound neo-noir thriller that explores the underworld of 1950’s Los Angeles in all its seedy glory.
4. Mystic River
Moving into the 2000’s, our first entry from the new millennium is Clint Eastwood’s Mystic River. This is one of the bleakest entries on this list and perhaps one of the bleakest mainstream Hollywood films of the century thus far, dealing with themes of childhood trauma, sexual abuse, murder, betrayal, and vengeance.
The story opens with three childhood friends, Jimmy, Sean, and Dave, playing street hockey in Boston, when suddenly a car arrives with two men who take Dave away. Years later, Dave (played to perfection by a fractured, insular Tim Robbins) is revealed to have been sexually abused by the men who abducted him and is still struggling to cope with his trauma when he is implicated in the murder of Jimmy’s teenage daughter, Katie. Jimmy (Sean Penn), a former con who has stepped away from his criminal life, pursues his own form of an investigation into the murder, while Sean (Kevin Bacon), now a detective with the Massachusetts State Police, closes in on the truth. The film’s dark subject matter is matched by Clint Eastwood’s cold, eerie visual palette— a seemingly interminable overcast Northeastern climate, all muted blue-gray tones, and hard, shadowy night exteriors. This film further cemented Clint’s place among the top of the world’s filmmaking ranks and proved him to be a studio-filmmaker unafraid of exploring the darker corners of human nature.
5. Layer Cake
Hopping across the pond for this next entry comes Matthew Vaughn’s energetic take on the British gangster film, Layer Cake. Vaughn cut his teeth producing fellow Brit Guy Ritchie’s smash-hits Lock, Stock, and 2 Smoking Barrels and Snatch, before turning over to directing his debut.
With Layer Cake, Vaughn proved himself as a worthy successor to Guy Ritchie’s hyper-kinetic, comedic, rough-and-tumble style with a slightly more polished, less tongue-in-cheek London-set action-crime movie. Daniel Craig, in his first major leading role, plays an unnamed cocaine trafficker who runs a tight ship and refrains from partaking in any of the industry’s dirty business. We find him just as he has one foot out the door ready for retirement, when suddenly he is summoned by his boss, Jimmy, who informs 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. He is also to search for an associate of Jimmy’s daughter, the drug-addicted Charlie, who has disappeared. As Craig’s character has no choice but to adhere, he finds himself slipping further and further into the areas of the drug business he had painstakingly worked his whole career to avoid. The movie trades in efficient storytelling, wise-cracking dialogue, brutal violence, and a star-making turn from a pre-Bond Daniel Craig.
6. The Departed
One of Scorsese’s very finest in his astonishing back-catalog, our next entry, The Departed, would make for a perfect double-feature with The Town. Despite the chorus of folks who dispute the Oscars for awarding Scorsese the Best Directing statue as a belated cop-out for past oversights (*ahem* Goodfellas *ahem*), this film is an absolute masterclass in big-budget, star-powered gangster movies.
Speaking of stars, this movie will go down as the final, truly great Jack Nicholson performance, whose turn as Irish Mob boss, Frank Costello, is one of the most memorable in movie history. Costello’s criminal enterprise extends to the Boston police department, as Colin Sullivan (Matt Damon), serves as a mole, while Billy Costigan (Leonardo DiCaprio), an informant for the police, has slowly been making his way up in Costello’s ranks. As Costello becomes convinced there is a mole in his gang, he urges Sullivan to dig him out, as Costigan becomes more and more suspicious that the police have their own double-crossing agent. This dual narrative structure (based upon acclaimed Hong Kong film Internal Affairs) is rightfully considered one of the great feats of screenwriting of the 21st century, but it’s truly the performances across the A-list ensemble—who collectively exude Boston grittiness and snarky-ness with such panache—that cements this film as the ne plus ultra of the Boston crime-drama.
7. Inside Man
Next on our list, Spike Lee’s grandiose take on the heist-movie. Another great pairing with The Town, this movie may be fleet-footed and lighter in tone, but it is no less hard-hitting and invigorating in execution. This is Spike at the absolute peak of his powers, masterfully orchestrating different tones and storylines into a unified, cohesive work of pop-entertainment.
Inspired by canonical bank-robbery movies like Dog Day Afternoon, but unlike that iconic film insofar that it is told mostly from the perspective of the police, who in this case is NYPD hostage negotiator, Keith Frazier, portrayed with ultra-suave bravado by Denzel Washington. The film picks up as a group of bank robbers—led by Clive Owen’s cryptic, cunning Dalton Russell—stick-up and take hostage the workers of a Manhattan bank owned by Arthur Case (Christopher Plummer), a domineering, stoic man trying his best to keep hidden a shady past. Always three steps ahead of the viewer, the film manages to do the near-impossible: provide laughs, thrills, twists, and a high-stakes moral-quandary at its core, without ever giving the impression that it even broke a sweat.
8. Lucky Number Slevin
Our third entry from 2006 (what a year!), Paul McGuigan’s underrated gem is often overshadowed by other slick-talking, fast-paced crime movies like Pulp Fiction, Snatch, or The Departed, but is no less worthy of your attention if you are a true crime movie aficionado.
In the early-mid-2000’s, Josh Hartnett showed promise as one of Hollywood’s major leading actors, and it’s a shame that he never truly capitalized on this (hopefully things will change as he’s slated to appear in two major upcoming productions, most notably Guy Ritchie’s next effort, Wrath of God). As the titular Slevin, Hartnett showed a rare combination of effortless poise, charm, and charisma. In a case of apparent mistaken identity and being in the wrong place at the wrong time, Slevin is found in the empty apartment of his missing friend Nick by a couple of henchman working for The Boss (Morgan Freeman), who, mistaking Slevin for Nick, informs him he must pay back a huge gambling debt. Alternatively, Slevin’s debt will be relieved if he agrees to kill the son of The Boss’ rival, The Rabbi (Ben Kingsley), who he believes had his son murdered. Upon being freed, Slevin is then kidnapped by the Rabbi’s henchman, and informed he also has to repay him a large gambling sum. What ensues is a carefully plotted, tightly scripted thriller with big-time movie stars perfectly cast in their roles, and more than a few tricks up its sleeve that will keep you guessing at every turn.
9. Gone Baby Gone
Next, we have Ben Affleck’s predecessor to The Town and his directorial debut, Gone Baby Gone. A seminal entry in the Boston crime-drama movie canon—and adapted from a book of the same name by Dennis Lehane, who also wrote the Mystic River novel which the movie was based on—this is a similarly bleak, unforgiving mystery thriller/portrait of people in crisis.
This story centres around the disappearance of a three-year-old girl, who Private Investigators Patrick (Casey Affleck, Ben’s brother), and his partner/lover, Angie (Michelle Monaghan) are hired to find. The girl’s mother (Amy Ryan, who was nominated for an Oscar for her performance), Helene, is a drug-addict who is revealed to have been involved in some shady dealings with her drug supplier. In similar narrative style to Mystic River, the plot leads you in one direction before completely upending your expectations. The movie ultimately serves as a morally ambiguous, emotionally charged, devastating and unwaveringly honest depiction of people struggling to do the right thing while at the most extreme cross-roads.
Released the same year as The Town, Takers takes the first spot on the 2010’s selection of our list. Trading The Town’s urban Bostonian grit for swanky Los Angeles glamour and high-wire set-pieces, Takers is the perfect movie for those who prefer their heist movies to be on the glitzier side and with a LOT of explosions, shootouts, and chase sequences.
Seasoned professional Gordon Cozier (Idris Elba), the leader of a highly well-orchestrated group of bank robbers, agrees to carry out one last job when a former member of his crew, Ghost (rapper T.I.), proposes a job that would set them all up for life; robbing an armored car carrying $12 million. On their tail are cops Jack Welles (Matt Dillon) and his partner Eddie Hatcher (Jay Hernandez). As the heist plays out and the cops zero-in, it becomes clear that Ghost’s motives for the heist might not be exactly all that they appear to be. If you’re looking for some exciting, easy-to-digest, standard Hollywood action fare, then this will be right up your alley.
11. Killing Them Softly
Next on the list, we have Andrew Dominik’s follow-up to his widely hailed yet underseen masterpiece, The Assassination of Jesse James by the Coward Robert Ford, which also saw the director reteaming with Brad Pitt. Here, they trade the American frontier setting and mythos for a modern tale of American idealism running its course.
Pitt stars as Jackie Cogan, a jaded, unusually talkative hitman hired to find three low-level crooks who stage a robbery during a mob-run illegal poker game in Boston. Before locating the three goons on the run in Florida, he enlists the help of a former colleague, Mickey (James Gandolfini), a New York hitman who is a shell of his former self and has taken up a life of heavy drinking and indulging in prostitutes while serving parole. Taking the source material (crime writer George V Higgin’s 1974 novel Cogan’s Trade) and updating it to 2008 recession-hit America, this film is a sardonic, violently chaotic cautionary tale that uses the backdrop of an America in financial crisis—while simultaneously under the impression that a new beginning is on the horizon with the election of Barack Obama—as a frame for a story of two hitmen whose cynicism and disillusionment only becomes stronger and stronger.
12. The Drop
The next addition to our list is the screenwriting debut of Dennis Lehane, Boston crime’s poet laureate, as he updates one of his short stories from 2009, Animal Rescue, and relocates his usual playing field of Boston to Brooklyn. The Drop is a smartly written, authentic-to-the-bone tale of blue-collar workers who are unwittingly tangled in a criminal underworld of mobsters and murderers.
The lead character, Bob Saginowski (Tom Hardy), is a quiet, soft-spoken bartender with a mysterious past, working for his cousin Marv (James Gandolfini) at a dive bar in Brooklyn. Some time ago, Marv forfeited ownership of his bar to a family of Chechen mobsters who use it as “the drop”— a safe-house for their illegal money to be collected. While working one night, the two of them are stuck-up and the bar is robbed by two masked assailants, which the Chechen mobsters threaten must be recompensed. This film is a solidly crafted thriller with unexpected warmth and heart beneath its thick layers of gruffness and machismo. Moreover, it’s an absolutely essential showcase for the brilliant Gandolfini’s talents, as this was sadly his swansong.
13. Hell or High Water
Next up is Scottish director David Mackenzie’s Texan-sun-scorched Hell or High Water. What easily could have been a mere simulacrum of No Country for Old Men instead turned out to be an undeniable sleeper hit and one of the best films of 2016.
Chris Pine and Ben Foster play brothers, Toby and Tanner, respectively, who rob banks across small towns in Western Texas. Their robberies are reserved purely for branches of Texas Midlands Bank, as this bank threatens foreclosure on their ranch property following their mother’s passing from illness and the debt she took on for the property through a reverse mortgage. On their trail is aging Texas Ranger Marcus Hamilton (portrayed with true aplomb by Jeff Bridges) and his close partner, Alberto Parker (played by underrated character actor Gil Birmingham). Despite trading in run-of-the-mill Western tropes, the film pumps new life into the genre with its soundly structured script, taut pacing, engaging characters, and elegiac, wistful tone.
Underseen upon release, the final movie on our list is Steve McQueen’s all-female heist movie, Widows. Penned by best-selling author Gillian Flynn, directed by Academy-Award winning filmmaker McQueen, and featuring an all-star cast of both seasoned veterans and up-and-coming talents, this film had all the makings for a global smash-hit. Despite its underwhelming box office returns, however, this film succeeds on almost all other fronts.
After a botched robbery of $2 million ends in Harry Rawlings (Liam Neeson) and his crew being gunned down by police, Veronica Rawlings (Viola Davis), Harry’s widow, receives a threatening visit from Jamal Manning (Brian Tyree Henry), the crime boss that Harry’s crew attempted to rob, and whose eyes are set on a local Southside Chicago political campaign. 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, Veronica enlists 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. McQueen’s concerns, however, extend beyond the heist itself; he gives us a view of life in southside Chicago and the socioeconomic discrepancies that result in characters like Jamal and his menacing, electric brother/enforcer, Jatemme (Daniel Kaluuya). Jettisoning one of the genre’s common tropes for a more sociopolitical and personal bend, this film focuses on a heist that is not really about money or power, but rather a way for these women to reclaim their identity and integrity.