Gangster moviesare a beloved staple, though cheering for the bad guys seems wrong in the grand scheme of things. Still, gangsters are usually of the people; it’s the men, women, and anyone elsewho doesn’t abide by rules but instead decides to tailor their own destinyno matter the risks. This is what attracts people to gangster movies—observing the possibilities and potential without taking the actual risk themselves.
Most gangster movies are dark and heavy, carrying a message that crime doesn’t pay and is often very messy, but there are also gangster movies that explore the genre a bit differently. Their authorsweren’t afraid to put a little fun and entertainment into the mix, adding a different spin to the story.Entertaining gangster moviesaren’t necessarily comedies, but they can make their viewers laugh; such movies are often rewatchable and fun, succeeding in what made them great in the first place—providing deliriously good entertainment.
10’Kung Fu Hustle' (2004)
Directed by Stephen Chow
Kung Fu Hustlemay be an unlikely entry, but it’s unmistakably a gangster movie. It follows residents of a Shanghai-based housing complex during the 1940s, and a couple of them, Sing (Stephen Chow) and Bone, have the ambition to become a part of the notorious local gang called the Axe Gang, led by the cold-blooded Brother Sum. When Sing and Bone intimidate a man by claiming they’re a part of the Axe Gang, Brother Sum takes a group of men with him to their housing complex to warn them. However, the residents of the complex, who look like ordinary older people,stop Sum and the Axe Gang with their incredible martial arts prowess.
Stephen Chow is a famous martial arts movie director, and his vision doesn’t stop at just exquisite fight scenes and choreographies. Heblends his movies with dark humor and gags, showing great skill in combining various genresinto one awesome movie. Fans ofmartial arts movieswill loveKung Fu Hustle, but fans of gangster movies should give this great cinematic feat a fair chance. They certainly won’t regret it, asKung Fu Hustleis seriously (and deliriously) entertaining.
Kung Fu Hustle
Watch on Apple TV
9’Midnight Run' (1988)
Directed by Martin Brest
Another less likely entry in the category,Midnight Run, follows gangster accountant Jonathan Mardukas (Charles Grodin) and bounty hunter Jack Walsh (Robert De Niro) on a “midnight run” from Chicago to Los Angeles. Walsh gets enlisted by the bail bondsman Eddie Moscone (Joe Pantoliano) to find Mardukas and deliver him to LA.Mardukas embezzles a large sum of money from his mob boss Jimmy Serrano(Dennis Farina) and runs away, leaving Serrano in a bind. Walsh and Mardukas board a plane to LA, but Mardukas has a phobia of flying, so he and Walsh have to get to LA by road traffic instead.
Midnight Runis a highly entertaining watch.The chemistry between De Niro and Grodin is excellent; they bounce off each other as opposites, with both actors delivering some of their best comedy work. While it may not fully be classified as a gangster movie, it has gangsters in it in the form of the badass Dennis Farina, so it’ll have to count. DirectorMartin Bresthad a hard time finding a partner for De Niro, who had his first foray into comedy withMidnight Run. Interestingly, De Niro agreed to do it to broaden his image from a movie tough guy to a more versatile actor and succeeded in creating a movie thatsteps out of the mouldof buddy comedies.
Midnight Run
A bounty hunter pursues a former Mafia accountant who is also being chased by a rival bounty hunter, the F.B.I., and his old mob boss after jumping bail.
Watch on Netflix
8’Gangster No. 1' (2000)
Directed by Paul McGuigan
WhenGuy RitchiemadeLock, Stock, and Two Smoking Barrelsin 1998, he’d created a genre of gangster movies that inspired many filmmakers to create something similar.Gangster No. 1doesn’t fall in that category, though it would be easy to assume it. It was written byLouis MellisandDavid Scintoas a play first and a movie later, and the movie was originally slated to be directed byJonathan Glazer. After whatMellis simply called “artistic differences,” the trio left the movie and went on to makeSexy Beast.
Paul Bettanystars as the younger version ofMalcolm McDowell’s character only known as The Gangster, andDavid Thewlissthrills as the notorious London gangster Freddy Mays. The story opens in the ’90s, with The Gangster (McDowell) learning that Freddy is getting out of prison after 30 years.This unravels The Gangster’s memories, reminiscing about his rise as a ruthless criminal. The director,Paul McGuigan, was a photographerbefore makingGangster No. 1; his eye for detail and a knack for portraying deliriously amusing and somewhat nauseating scenes of violence are completed by McDowell’s chaotic narration and Bettany’s intense performance.Gangster No. 1is not a comedy, but it’s incredibly entertaining because itfollows the staples of the genre while breaking the mould.
Gangster No. 1
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7’Sexy Beast' (2001)
Directed by Jonathan Glazer
After leavingGangster No. 1, Louis Mellis, David Scinto, and Jonathan Glazer (in his directorial debut) joined the production ofSexy Beast.Both movies have a similar flair for violence, but Glazer’s point of view is much different from McGuigan’s.Sexy Beastis often considered one of the most iconic British crime movies, and not for nothing. It has an excellent script, brilliant performances byRay WinstoneandSir Ben Kingsley, and a visually stunning setting that contradicts the gritty, dirty actions done by cruel gangsters.
Sexy Beasttakes place in Costa del Sol, Spain. The retired criminal, Gal Dove (Winstone), is taking his time tanning in the Spanish sun, next to his pool in his gorgeous villa with his beautiful wife. ButGal’s plans to do nothing are hindered when a sociopathic criminal, Don Logan (Kingsley), visits his villa, asking him to do a heist. Though every performance in the movie carriesSexy Beastto new heights, Kingsley’s is by far the most memorable and enjoyable.Roger Ebertdescribed it best: “He’s angry, seductive, annoyed, wheedling, fed up, ominous, and out of his mind with frustration. I didn’t know Kingsley had such notes inside him.”
Sexy Beast
With their reputation growing across London, thieves Gal and Don are recruited by renowned criminal boss Teddy Bass for a high-stakes job. But as they continue to rise in the criminal world, they find their lives changed forever.
6’Snatch' (2000)
Directed by Guy Ritchie
Guy Ritchie tapped into the gangster genre withLock, Stock, and though it’s highly entertaining,Snatchhas a slight upper hand because it’s hard to forget. Every line in it is memorable, and each character is boldly unique. The allure ofSnatchalso lies in its marketability because ofBrad Pittin the starring role. The stylish character title cards, the fast-paced editing, the intertwined storylines…There’s so much to love and enjoy about this gangster black comedy.
Snatch follows Turkish (Jason Statham) and Tommy (Stephen Graham), small fry who represent a boxer called Gorgeous George. The three visit the traveler community and start negotiating for a caravan with Mickey (Brad Pitt), an amateur boxer. When Mickey knocks out George during a fight,Turkish and Tommy have no choice but to put Mickey up for a fight instead, if they can contain the unpredictable and hot-headed Mickey. There are other subplots inSnatch, but explaining them would take a dissertation; however, the story isn’t overly convoluted, after all. The ensemble is portrayed through hilarious and often quite violent scenes that stay in one’s mind long after the movie ends.
Unscrupulous boxing promoters, violent bookmakers, a Russian gangster, incompetent amateur robbers and supposedly Jewish jewelers fight to track down a priceless stolen diamond.
Watch on Hulu
5’Layer Cake' (2004)
Directed by Matthew Vaughn
Longtime Guy Ritchie collaboratorMatthew Vaughntypically served as an executive producer on Ritchie’s films; when he got into directing himself, he madeLayer Cake, a uniquely layered (pun intended) gangster black comedy similar to his work with Ritchie but stilldifferent in style, flair, and character.Daniel Craigleads the rich ensemble cast as an unnamed gangster and is joined byTom Hardy,Michael Gambon,Sienna Miller, andJamie Foreman, theson of a real-life London gangster,Freddie Foreman(Jamie also stars inGangster No. 1).
Layer Cakeis about a dealer credited only as XXXX (Daniel Craig). He doesn’t approve of the gangster lifestyle because he dislikes violence, but doesn’t have qualms about drug distribution.When XXXX tries to retire, he’s dragged into doing two final tasks for the hardened gangster Jimmy(Kenneth Cranham). The plot becomes all the more convoluted and twisted as the movie progresses, and Daniel Craig carries the movie as the intelligent dealer with his eyes on each next step.Layer Cakeis brilliantly entertaining and one ofthe best British gangster movies.
Layer Cake
A successful cocaine dealer gets two tough assignments from his boss on the eve of his planned early retirement.
Watch on Amazon Prime
4’Reservoir Dogs' (1992)
Directed by Quentin Tarantino
The entertainment factor inReservoir Dogscomes from several factors: the unique, dialogue-packed screenplay (aQuentin Tarantinostaple), the brilliant ensemble cast made up of legendary actors (fromHarvey KeitelandSteve BuscemitoTim RothandMichael Madsen), and the movie’s overall importance to cinema and independent film in general. Empire Magazine namedReservoir Dogsone ofthe greatest American independent movies. This was also Quentin Tarantino’s directorial debut, based on a short he previously made.
Reservoir Dogsfollows eight men, out of whom six only have aliases based on colors; they’re sitting at a diner, preparing for a diamond heist,which later goes wrong, and the men become suspicious that one of them is an informant.Though they’re not technically gangsters but thieves, Mr. White (Keitel) shows extreme gangster-like tendencies, while Mr. Blonde (Madsen) is a bloodthirsty ex-con with nothing to lose.Reservoir Dogsis a pretty violent cult classic, but it’s also incredibly entertaining for anyone with a strong stomach.
Reservoir Dogs
Watch on Tubi
3’In Bruges' (2008)
Directed by Martin McDonagh
Martin McDonagh’s talent for combining belly-laughing black comedy with gritty action is pretty unique;all of his movies are deliriously entertaining, no matter how dark they get.In Brugesgets pretty dark, pretty quickly, thanks toColin Farrell’s exquisite performance as Ray, the broody hitman. He is accompanied by the always charmingBrendan Gleesonas the more experienced and hedonistic Ken. The two hitmen await further instructions from their gangster boss Harry (Ralph Fiennes) while posted up in Bruges, Belgium.
Ken and Ray (in his first hit) did a hit job that resulted in the killing of an innocent bystander. While Ken is more experienced and does his best to enjoy his time in Bruges despite the circumstances, Ray’s despondent attitude can’t be diminished by any of the beautiful buildings or Ken’s efforts. While they wait for Harry,the two men get into different troubles, ranging from lovely to downright bizarre.In Brugesis truly one ofthe funniest gangster moviesever made, even if it doesn’t prominently feature as many gangsters.
Guilt-stricken after a job gone wrong, hitman Ray and his partner await orders from their ruthless boss in Bruges, Belgium, the last place in the world Ray wants to be.
2’The Gentlemen' (2020)
When one thinks of the phrase “deliriously entertaining,“The Gentlemenoften comes to mind. Guy Ritchie’s latest Cockney gangster featurecombines all the things that made him famous with his years of influence and experience in the industry. This time, the cast is packed with superstars, from living legends likeMatthew McConaugheyandHugh Grantto brilliantly underrated performers likeCharlie HunnamandHenry Golding. The movie was well-received, though people did compare it to Ritchie’s older work likeLock, Stock,andSnatch.
The Gentlemenfollows Mickey Pearson (McConaughey), an American marijuana kingpin in London. His empire ‘grows’ below the lands of aristocrats who need the money for estate upkeep. Mickey decides to sell his business to the cleanest bidder, become a legal businessman, and retire with his wife (Michelle Dockery). Buthis plans are hindered by various factions, from the Asian drug lords to the local boxing gang. It’s a classic Ritchie conundrum, with some intensely amusing monologues from Hugh Grant, who plays a reporter, and some memorable eye candy moments from Hunnam (this is especially important to anyone who cares about Hunnam).
The Gentlemen
Mickey Pearson, a wealthy American living in London, has built a successful marijuana empire. Planning to cash out, he announces his intention to sell the business, sparking a wave of criminal intrigue. Rival gangs, ambitious newcomers, and corrupt officials all vie for control, leading to a series of betrayals and power plays. As Mickey tries to secure his retirement, he faces challenges from all sides, including a cunning private investigator who complicates matters further.
1’Goodfellas' (1990)
Directed by Martin Scorsese
Everyone knows the scene fromGoodfellaswhenJoe Pesci’s Tommy DeVito asksRay Liotta’s Henry Hill, “What do you mean I’m funny?” This intense, electric scene ends in laughter, but not before it intimidates every single participant in the scene, including the viewers.Goodfellasis a true story; it’s bloody, violent, and full of villains. But, damn, if it’s not exceptionally entertaining. Possiblythe best crime movie of all timeand simply one of the best movies ever made,Goodfellasranks above the rest with its storytelling,perfect performances, and inspirationof the surreal rise and fall of Henry Hill.
Goodfellasstarts and ends with Henry’s (Ray Liotta) narration.He talks the viewers through his years as a gangster, from being a street crook to making major moves. He often works with Jimmy Conway (Robert De Niro), Tommy DeVito (Pesci), and Paulie Cicero (Paul Sorvino). Henry’s path is messy and treacherous, but his mesmerized attitude toward the gangster lifestyle immerses the viewers in what might be. Even when things end up differently for him, Henry’s constant desire to be relevant and not be “a schnook” lives on.
Goodfellas
The story of Henry Hill and his life in the mafia, covering his relationship with his wife Karen and his mob partners Jimmy Conway and Tommy DeVito.
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