Movies Like I Always Wanted to Be a Gangster
If you loved I Always Wanted to Be a Gangster's Drama and Comedy storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
Things Change
Jerry, a misfit Mafia henchman, is assigned the low-level job of keeping an eye on Gino, a shoe repairman fingered by the Mob to confess to a murder he didn't commit. But Gino's mistaken for a Mafia boss, and the two are suddenly catapulted to the highest levels of mobster status. Only friendship will see them through this dangerous adventure alive!
Panic
Alex is going through a midlife crisis and it has become a very difficult time for him. His marriage is struggling, he's worried about his son, and his job of killing people for his family has become the most stressful part of his life. He seeks the help of a therapist and meets a woman in the waiting room that he connects with.
Small Apartments
When a clumsy deadbeat accidentally kills his landlord, he must do everything in his power to hide the body, only to find that the distractions of lust, the death of his beloved brother, and a crew of misfit characters force him on a journey where a fortune awaits him.
Hold-up
Dressed as a clown, the clever rascal Grimm holds up the most secure bank of Montreal and takes 30 hostages. While confusing and ridiculing the police with his strange behavior, he calmly manages to rid the bank of a fortune. But then an unsatisfied companion arouses trouble...
Defendor
A crooked cop, a mob boss and the young girl they abuse are the denizens of a city's criminal underworld. It's a world that ordinary Arthur Poppington doesn't understand and doesn't belong in, but is committed to fighting when he changes into a vigilante super-hero of his own making, Defendor. With no power other than courage Defendor takes to the streets to protect the city's innocents.
Breaking News in Yuba County
An overlooked pencil-pusher catches her husband in bed with another woman, the shock of which causes him to die of a heart attack. So she buries his body and takes advantage of the growing celebrity status that comes from having a missing husband. But she quickly finds herself in over her head, dodging cops and criminals, all while trying to keep the truth from her sister, a local news anchor who’s desperate for a story.
Amateur
A man wakes up in an alley, bleeding and with no memory of who he is. He stumbles into a coffee shop and is befriended by a charitable ex-nun who is failing in her attempts to write marketable pornography.
Winged Creatures
A psychotic man opens fire in a diner, murdering numerous people before killing himself. The survivors struggle in different ways following this horrendous event: a doctor doubts his own instincts and elects to use an experimental medical procedure on his wife, while a gambler believes he's on a lucky streak. A waitress begins engaging in promiscuous sex, and a young girl whose father is among the dead gains unexpected fame.
More Movies Like I Always Wanted to Be a Gangster
The First, the Last
Apocalyptic neo-western about two gangsters, a town full of crazy people and Jesus...
Intermission
A raucous story of the interweaving lives and loves of small-town delinquents, shady cops, pretty good girls and very bad boys. With Irish guts and grit, lives collide, preconceptions shatter and romance is tested to the extreme. An ill-timed and poorly executed couple's break-up sets off a chain of events affecting everyone in town.
Masquerade
Adrien, an attractive dancer whose career was shattered by a motorcycle accident, squanders his youth in idleness. His life changes when he meets Margot, who lives off scams and amorous manipulations.
Thick as Thieves
Two master thieves go at odds with one another as one sets the other up for a crime. The first, a suave pro who does his job and then hides in his own privacy, listening to old jazz records and caring for his ailing dog, Wally. The other is a local gangster with a taste for the finer life, who decides to eliminate the competition. This ignites a war between the two men and their aides. An angry mob boss and a female police officer try to sort the mess before things get too out of hand.
The Damned Don't Cry
Fed up with her small-town marriage, a woman goes after the big time and gets mixed up with the mob.
Paris by Night
Police commander Simon Weiss, head of the division that supervises Paris’s demi-monde, starts out on his nightly tour of bars, discos and strip clubs, making sure once again that the owners don’t bend the rules too far. Weiss knows he’s between a rock and hard place: it’s obvious that criminal gangs run rampant in his special domain, and even more obvious that they’re protected by higher-ups in the department.
The Enforcer
A noir thriller set in Miami, the film follows an enforcer who discovers his femme fatale boss has branched out into cyber sex trafficking, putting a young runaway he’s befriended at risk. He sacrifices everything to save the young girl from the deadly organization he’s spent his life building.
Blindspotting
Collin must make it through his final three days of probation for a chance at a new beginning. He and his troublemaking childhood best friend, Miles, work as movers, and when Collin witnesses a police shooting, the two men’s friendship is tested as they grapple with identity and their changed realities in the rapidly-gentrifying neighborhood they grew up in.
One Night at McCool's
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...
Gangsters
Franck Chaievski and Nina Delgado are two undercover detectives of a French special force trying to identify two corrupts members of the Paris Police Force. Franck is pretending to be a gangster and Nina a prostitute living with him, and involved in a robbery of a fortune in diamonds, having seven deaths and some injured persons.
Bad
Hazel runs a beauty salon out of her house, but makes extra money by providing ruthless women the oppurtunity to perform hit jobs. L.T. is a parasite, and contacts Hazel looking for work after he runs out of money. She is reluctant to use him for a hit, since she prefers using women, but decides to try him on a trial basis. Meanwhile, the cop she pays off wants an arrest to make it look like he's doing his job, but Hazel doesn't want to sacrifice any of her "associates". The sleazy side of life is explored in this delightfully dark and deadpan film.
Above the Rim
Story of a promising high school basketball star and his relationships with two brothers, one a drug dealer and the other a former basketball star fallen on hard times and now employed as a security guard.
Why These Movies Are Similar
These recommendations share core qualities with I Always Wanted to Be a Gangster (2008): Drama and Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of I Always Wanted to Be a Gangster.
See full details for I Always Wanted to Be a Gangster (2008)