You won't want to refuse what these eccentric mafia movies have to offer...
Since its debut three weeks ago, Tulsa King has become the latest small screen success for Paramount+, as Sylvester Stallone's displaced gangster story has pleased both audiences and critics alike.
Bosque Ranch Productions
With the news breaking this week that Tulsa Kingwill return for a second season next year, this writer was inspired to assemble a number of off-beat and unusual gangster movies to help keep fans of this crime comedy series satiated between episodes and/or seasons.
1. Gone with the Pope (2010)
Grindhouse Releasing via YouTube
Cast: Duke Mitchell, Lorenzo Dardado, Jeanne Hibbard, and Jim LoBianco
Director: Duke Mitchell
Runtime: 83 Minutes
Rating: Unrated
Rotten Tomatoes
The self-anointed “King of Palm Springs” Duke Mitchell is a larger-than-life figure who became an underground figure in a number of disciplines, whether it be slapstick comedy, crooning, or independent filmmaking. Often starring in his own movies, both of which fall firmly into offensive exploitation film territory, none feels closer to Tulsa King more than Gone with the Pope, Mitchell’s sophom*ore feature that was left uncompleted in the late ‘70s before being finished, restored, and released in 2010. Inspired by The Godfather (although unbelievably so), Gone with the Pope follows four ex-mobsters who venture to Rome to kidnap the Pope and demand a ransom from every Catholic on Earth.
2. Killing Them Softly (2012)
PLAN B ENTERTAINMENT / Cortesia Album / Alamy
Cast: Brad Pitt, Scoot McNairy, James Gandolfini, Ray Liotta, and Ben Mendelsohn
Director: Andrew Dominik
Runtime: 97 Minutes
Rating: R
A genuinely nerve-wracking allegory about capitalism and post-war individualism, Andrew Dominik’s stylish and hard-hitting film follows a frustrated mafia hitman (Brad Pitt) who is hired with killing those responsible for a mob card game robbery, even though his plans to do so fail to unfold as planned. With incredible performances all around, including an amazing James Gandolfini as a washed-out, hedonistic assassin and a stellar Ray Liotta as a low-level mafioso who is wrongfully accused of staging the robbery, Killing Them Softly is an outside-the-box, dialogue-heavy gangster film that mines the most out of its slowest moments while being simultaneously unafraid to drop your jaw with shocking, hyper-realistic violence.
3. Dead or Alive (1999)
Daiei Motion Picture Company / Photo 12 / Alamy
Cast:Riki Takeuchi, Show Aikawa, Renji Ishibashi, Susuu Terajima, and Shingo Tsurumi
Director:Takashi Miike
Runtime:105 Minutes
Rating:Not Rated
Rotten Tomatoes
Helmed by one of Japan’s most prolific and bold filmmakers, Takashi Miike,Dead or Aliveis a different breed of yakuza film, pitting an ambitious small-time gangster against a detective indebted to a more powerful yakuza boss. However, instead of the traditional gangster movie “cat-and-mouse” game between cop and criminal,Dead or Alivedecides to lean into chaos, where any and every character can die at the drop of a hat and the violence escalates to bizarre heights.Dead or Alivetruly cements itself unlike any gangster movie out there with a final confrontation that’ll leave you absolutely flabbergasted in the best way possible.
4. Sexy Beast (2000)
Channel Four / Maximum Film / Alamy
Cast: Ray Winston, Ben Kingsley, Ian McShane, and Amanda Redman
Director: Jonathan Glazer
Runtime: 88 Minutes
Rating: R
The feature film directorial debut of Jonathan Glazer, who would later find global acclaim with 2013’s Under the Skin, Sexy Beast is the rare gangster film about life after crime, largely focusing on the foul-mouthed battle of wits between the happily retired gangster Gal (Ray Winstone) and the sociopathic criminal associate, Don (Ben Kingsley, who was nominated for an Oscar for his performance). Rejecting an offer to return to London for an important bank heist, Gal faces the unpredictable and increasingly vulgar wrath of Don, inevitably leading to more drastic measures. Prioritizing style over substance, Sexy Beast is a darkly comic masterpiece unlike any other gangster film in the subgenre.
5. A History of Violence (2005)
New Line Cinema / Pictorial Press Ltd / Alamy
Cast: Viggo Mortensen, Maria Bello, Ed Harris, Ashton Holmes, and William Hurt
Director: David Cronenberg
Runtime: 96 Minutes
Rating: R
Adapted from the 1997 graphic novel of the same name from John Wagner and Vince Locke, anyone familiar with the work of David Cronenberg would know that the horror maestro’s inaugural attempt at a gangster film would be anything but conventional. For those unfamiliar, A History of Violence surrounds an unassuming diner owner (Viggo Mortensen) who is showered with media attention after killing a pair of petty criminals during an attempted robbery, drawing the attention of an ominous criminal (Ed Harris) who accuses him of being a missing prominent mobster. Also featuring Maria Bello and the late William Hurt, who was nominated for an Oscar for less than nine minutes of screentime, A History of Violence remains one of the best neo-noirs of the ‘00s and presents a reverse-engineered gangster film that feels borderline hypnotic in nature.
6. Mickey Blue Eyes (1999)
Collection Christophel / Simian Films / Castle Rock / Alamy
Cast: Hugh Grant, Jeanne Tripplehorn, James Caan, Burt Young, and Joe Viterelli
Director: Kelly Makin
Runtime: 103 Minutes
Rating: PG-13
Rotten Tomatoes
In the late 1990s, Hollywood somehow became enamored with “fish-out-of-water” mafia comedies, whether it be in the Matthew Perry-starring The Whole Nine Yards (and its very, very bad sequel) or the Joe Pesci-starring 8 Heads in a Duffel Bag. But few were as high profile as Mickey Blue Eyes, in which Hollywood decided to mix up both the mafia subgenre and romantic comedy genre by having British heartthrob Hugh Grant trying to win over the heart of a mob heiress. Anchored by a gruff supporting performance by a dedicated James Caan, Mickey Blue Eyes isn’t a grand slam of either genre, but the film is more fun and charming than the script would normally allow, especially as Grant begins having fun playing toward (and against) his public image.
7. Find Me Guilty (2006)
Cinematic Collection / Alamy / Crossroads Entertainment
Cast: Vin Diesel, Peter Dinklage, Linus Roache, Ron Silver, and Raúl Esparza
Director: Sidney Lumet
Runtime: 124 Minutes
Rating: R
Rotten Tomatoes
It’s very strange to consider one of the final feature films from legendary filmmaker Sidney Lumet, known for films such as 12 Angry Men and Dog Day Afternoon, was a mafia comedy starring The Fast and the Furious stalwart Vin Diesel and future Game of Thrones breakout Peter Dinklage. Based on the true story of the longest mafia trial in American history, so much so that the real court transcripts were used for the testimony dialogue, Diesel plays Jackie DiNorscio, an incarcerated mobster who is brought to trial on racketeering charges who decided to represent himself in court. A very different character for Diesel, the film brings both drama and humor to such a process in a way that can really only be compared to one other film: My Cousin Vinny.
8. Snatch (2000)
Columbia Pictures /Pictorial Press Ltd / Alamy
Cast: Brad Pitt, Jason Statham, Benicio del Toro, Dennis Farina, and Vinnie Jones
Director: Guy Ritchie
Runtime: 98 Minutes
Rating: R
Rotten Tomatoes
After essentially creating a new genre and making his name with his stylized British gangster film,Lock, Stock and Two Smoking Barrels, director Guy Ritchie’s sophom*ore feature film has since become his undisputed masterwork of the genre, Snatch. An ensemble piece filled with actors chewing up scenery with colorful and surreal characters, including Brad Pitt as a transient boxer, Vinnie Jones as a brash bounty hunter, Dennis Farina as a wise-ass jeweler, and Jason Statham as a smooth-talking boxing promoter, Snatch did for Ritchie was Evil Dead II did for Sam Raimi, perfecting a fun, new breed of gangster film with a bigger profile and cementing new stars alongside established Hollywood big shots.
9. Why Don’t You Play in Hell? (2013)
Drafthouse Films via YouTube / Via youtu.be
Cast: Jun Kunimura, Shinichi Tsutsumi, Hiroki Hasegawa, Fumi Nikaidô, and Gen Hoshino
Director: Sion Sono
Runtime: 129 Minutes
Rating: Not Rated
Rotten Tomatoes
An oddly inspirational, darkly humorous, and absolutely manic film about bloodthirsty yakuza warfare and the magic of independent filmmaking, Why Don’t You Play in Hell? follows a group of languishing punk-rock filmmakers whose desire to make “the greatest movie ever made” comes to fruition when they accidentally stumble into a gang war, in which rival yakuza leaders battle over a decades-spanning grudge. Referential, hilarious, and incredibly blood, Why Don’t You Play in Hell? completely shakes up all pre-existing notions of gangster films with childlike whimsy and Tarantino-esque style; imagine mixing Kill Bill and The Fabelmans and you might know what you’re walking into with this weird and wild cult flick.
10. The Bag Man (2014)
Prod DB / Cinedigm / TinRes Entertainment / Alamy
Cast: John Cusack, Dominic Purcell, Crispin Glover, Rebecca Da Costa, and Robert De Niro
Director: David Grovic
Runtime: 108 Minutes
Rating: R
Rotten Tomatoes
In this peculiar little gangster movie that leans closer to the works of David Lynch and Steven Soderbergh than that of Scorsese and De Palma, The Bag Man follows a professional mob hitman (John Cusack) who is hired by a brutal gangster (Robert De Niro) to retrieve a bag and await for his arrival at a remote hotel, under the condition that no one opens the bag under any circ*mstance. After killing an apparently volatile lower-level thug, the assassin comes in contact with a number of bizarre people around the motel, including FBI agents, an eccentric desk clerk, a headstrong sheriff, a sex worker, and her pimps, all of whom may have their own motivations to take the mysterious bag for themselves. The Bag Man isn’t likely going to blow your mind, but it’s certainly a quirky and unique crime flick certain to keep you entertained thanks to its solid cast.
11. In Bruges (2008)
Universal Pictures / Pictorial Press Ltd / Alamy
Cast: Colin Farrell, Brendan Gleeson, Ralph Fiennes, Clémence Poésy, and Ciarán Hinds
Director: Martin McDonagh
Runtime: 107 Minutes
Rating: R
Rotten Tomatoes
A foul-mouthed and absolutely astounding gangster flick driven by razor-sharp dialogue and a darkly comedic wit, In Bruges, is the directorial debut of acclaimed filmmaker and playwright Martin McDonagh, which surrounds two Irish hitmen (Colin Farrell & Brendan Gleeson) that are sent by their temperamental mob boss (Ralph Fiennes) to travel to Bruges, Belgium after a contract killing gone wrong. But as the hitmen endear themselves to their unfamiliar surroundings and new neighbors, an order comes down that pits each trigger-happy gangster against one another. Brash and violent yet surprisingly poignant, In Bruges is the rare mob film that feels intimate and mines comedy, drama, and plentiful narrative twists from that intimacy.
12. Analyze This (1999)
Warner Bros. / Pictorial Press Ltd / Alamy
Cast: Robert De Niro, Billy Crystal, Lisa Kudrow, Joe Viterelli, and Chazz Palminteri
Director: Harold Ramis
Runtime: 103 Minutes
Rating: R
Rotten Tomatoes
After Martin Scorsese’s one-two punch of Casino and Goodfellas and Quentin Tarantino’s game-changing Pulp Fiction, there weren’t many places left for the gangster movie genre to go in the 1990s. The same could be said for Robert D Niro, who attempted to balance his “tough guy” criminal roles in Heat and Ronin with subversive parts in Mary Shelley’s Frankenstein, Cop Land, and Sleepers. However, these circ*mstances converged to alter the paths of both mob movies and De Niro’s career for the better with Analyze This, a hysterical twist on mafia film tropes pairing De Niro and Billy Crystal that oddly aligned thematically with The Sopranos, which basically helped reinvent the genre as well.
13. Sonatine (1993)
Shouchiku Daichii Kougyo / RGR Collection / Alamy
Cast: Takeshi Kitano, Aya Kokumai, Tetsu Watanabe, Susumu Terajima, and Ren Osugi
Director: Takeshi Kitano
Runtime: 94 Minutes
Rating: R
From cult Japanese filmmaker/actor Takeshi Kitano (a/k/a Beat Takeshi), Sonatine is a critically acclaimed yakuza yarn about a disillusioned, aging gangster who is tasked to mediate a dispute between allied gangs, only to find himself in the middle of an ambush. Rallying the survivors of the attack, the gangster takes refuge at a remote beach property, where the group turns desperate when faced with one of their biggest threats: maddening boredom. Comical, playful, and fairly unpredictable, Sonatine became a critical and commercial hit for Kitano, and even in spite of its unusual narrative, the film was ranked No. 2 on Complex’s 25 Best Yakuza Movies in 2015.
14. The Crew (2000)
Globe Photos / ZUMAPRESS.com / Alamy
Cast: Richard Dreyfuss, Burt Reynolds, Dan Hedaya, Seymour Cassel, and Carrie-Anne Moss
Director: Michael Dinner
Runtime: 87 Minutes
Rating: PG-13
A title more infamous as a box office bomb and critical disaster, The Crew attempted to make a comedy about elderly former mobsters whose main appeal was assembling a cast of celebrated actors such as Burt Reynolds, Richard Dreyfuss, Dan Hedaya, and Seymour Cassell. Also featuring Jennifer Tilly, Carrie-Anne Moss, and Jeremy Piven, the film surrounded retired mobsters who plan one last crime to prevent their eviction from their retirement community, only to accidentally run afoul of drug smugglers. While the movie is definitely on the lower rung of mob comedies from its time, the cast has an infectious chemistry and there are a number of inspired set pieces that keep it from becoming a complete bust.
15. Things to Do in Denver When You’re Dead (1995)
Woods Entertainment /AJ Pics / Alamy
Cast: Andy Garcia, Christopher Lloyd, Fairuza Balk, Bill Nunn, and Treat Williams
Director: Gary Fleder
Runtime: 114 Minutes
Rating: R
Though this off-the-wall gangster flick has been criminally misrepresented as “Tarantino lite,” Things to Do in Denver When You’re Dead follows an indebted gangster who is summoned by a crime lord to help convince a young woman to return to her depraved ex-boyfriend, who happens to be the crime lord’s son. Assembling his gang of wayward friends, their plan goes terribly wrong, putting all of them in the crosshairs of an effective and cold-hearted hitman. Featuring an ensemble cast of fantastic character actors, including Christopher Lloyd, Bill Nunn, Steve Buscemi, and Fairuza Balk, and some stylistic visual choices, Things to Do in Denver When You’re Dead certainly deserves to find a second life as a cult classic.
16. The Outfit (2022)
Filmnation Entertainment / Scoop Productions / Album / Alamy
Cast: Mark Rylance, Zoey Deutch, Dylan O'Brien, Nikki Amuka-Bird, and Johnny Flynn
Director: Graham Moore
Runtime: 105 Minutes
Rating: R
Unfolding almost like a one-location play, Graham Moore’s moody and intense The Outfit transforms the standard gangster movie into a suspense-driven whodunnit surrounding a mafia informant, a tape that could bring down an entire criminal organization and a lowly tailor whose shop operates as an informal delivery system for a dangerous nationwide mob syndicate. Anchored by a coy and committed Mark Rylance while hosting stellar performances from both Zoey Deutch and Dylan O’Brien, The Outfit plays with your expectations around every corner while continuously increasing the tension and building the dangerous universe within the story with every shocking reveal and explosive turn of events.
17. Get Shorty (1995)
MGM /Maximum Film / Alamy
Cast: John Travolta, Gene Hackman, Rene Russo, Danny DeVito, and James Gandolfini
Director: Barry Sonnenfeld
Runtime: 105 Minutes
Rating: R
An old-school, cool-as-ice gangster story somehow integrates effortlessly with Hollywood satire in Get Shorty, Barry Sonnenfeld’s laugh-out-loud adaptation of Elmore Leonard’s 1990 novel of the same name. With an all-star cast headlined by John Travolta, fresh off his career-revitalizing role in Pulp Fiction, Get Shorty follows a loan shark from Miami whose attempt to collect an outstanding debt incidentally leads him to Hollywood, where he decides to produce a movie based on the collection attempt itself. Inspired by a real-life loan shark, who appears in the film, Get Shorty is the kind of strange mob movie that fires on every cylinder, winning with critics and audiences alike and eventually leading to a high-profile sequel, Be Cool.
18. Looper (2012)
PictureLux / The Hollywood Archive / Alamy
Cast: Bruce Willis, Joseph Gordon-Levitt, Emily Blunt, Paul Dano, and Jeff Daniels
Director: Rian Johnson
Runtime: 119 Minutes
Rating: R
Rotten Tomatoes
At its most basic, Looper is a science-fiction thriller that pits a past and future version of a contract killer against one another, so it wouldn’t be out of the ordinary to forget that Looper is, indeed, a mafia movie. Surrounding a Kansas City crime syndicate in the future as they send their enemies to the past via time travel to be killed and disposed of accordingly, including their own contract killers to rid themselves of loose ends, there’s a whole foundation of the story driven by the mafia story, including a mafia underboss played by Jeff Daniels, and the wrath of their influence, as established by Old Joe’s tragic background and Seth’s horrifying punishment for breaking their rules.
19. Mad Dog & Glory (1993)
Universal Pictures / Alamy
Cast: Robert De Niro, Uma Thurman, Bill Murray, Kathy Baker, and David Caruso
Director: John McNaughton
Runtime: 96 Minutes
Rating: R
Imagine, if you will, putting together a romantic drama that takes place against the backdrop of the criminal underworld: of course, if you’re casting the mild-mannered, meek everyman, who better than Robert De Niro, fresh off of his bedazzling turn in Goodfellas, and if you need an intimidating, ruthless gangster, you turn to… Bill Murray?! Directed by John McNaughton, the provocative director of Henry: Portrait of a Serial Killer, Mad Dog & Glory is the type of mafia movie that audiences couldn’t quite wrap their head around, even if critics were more appreciative of the big swings and the underlying charm of the film.
20. My Blue Heaven (1990)
Warner Bros. / Ronald Grant Archive / Alamy
Cast: Steve Martin, Rick Moranis, Joan Cusack, Melanie Mayron, and Carol Kane
Director: Herbert Ross
Runtime: 95 Minutes
Rating: PG-13
Rotten Tomatoes
One of the two 1990 movies based on the life of Henry Hill, the other being Goodfellas, My Blue Heaven was written by the late, great Nora Ephron, who based this mafia comedy based on research from her husband, Wiseguy author, Nicholas Pileggi. My Blue Heaven stars Steven Martin as “Vinnie Antonelli,” a mobster in the Witness Protection Program whose over-the-top lifestyle interferes with his pre-testimony protocols, despite the best efforts of his federal agent-turned-friend (Rick Moranis). A cult classic initially conceived as a costarring vehicle with Martin and Arnold Schwarzenegger, My Blue Heaven approaches the tragic ending of Goodfellas as the beginning of a humorous tale of cultures clashing and an unlikely friendship, which makes it all the more memorable.
21. King of New York (1990)
Collection Christophel / RnB / Seven Arts / Carolco Pictures / New Line Cinema / Alamy
Cast: Christopher Walken, David Caruso, Laurence Fishburne, Victor Argo, and Wesley Snipes
Director: Abel Ferrara
Runtime: 104 Minutes
Rating: R
Rotten Tomatoes
An ultraviolent gangster film with an art film flair, King of New York offers one of the most memorable lead performances of Christopher Walken’s career as Frank White, a ruthless, soft-spoken gangster looking to rebuild his drug empire on the streets of New York after being released from prison. Also assembling a fantastic ensemble cast including Laurence Fishburne, David Caruso, Wesley Snipes, Giancarlo Esposito and Victor Argo, Abel Ferrara’s unforgettable crime film offers a lot of stranger, quieter moments paired with explosive and unforgettable moments of brutal violence that often feel like the blueprint for the tone of The Sopranos less than a decade later.
