Movies Like Meeting the Boss

If you liked Meeting the Boss, a movie directed by Nathaniel Demuth, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Donnie Brasco (1997)
★ 7.5/10
An FBI undercover agent infiltrates the mob and identifies more with the mafia life at the expense of his regular one.
2
10th & Wolf (2006)
★ 5.9/10
A former street thug returns to his Philadelphia home after a stint in the military. Back on his home turf, he once again finds himself tangling with the mob boss who was instrumental in his going off to be a soldier.
3
Hoodlum (1997)
★ 6.5/10
In 1934, the second most lucrative business in New York City was running 'the numbers'. When Madam Queen—the powerful woman who runs the scam in Harlem—is arrested, Ellsworth 'Bumpy' Johnson takes over the business and…
4
Criminal Activities (2015)
★ 5.9/10
Four young men make a risky investment together that gets them into trouble with the mob.
5
Absolution (2024)
★ 5.9/10
An aging ex-boxer gangster working as muscle for a Boston crime boss receives an upsetting diagnosis. Despite a faltering memory, he attempts to rectify the sins of his past and reconnect with his estranged children…
6
2 Guns (2013)
★ 6.5/10
A DEA agent and an undercover Naval Intelligence officer who have been tasked with investigating one another find they have been set up by the mob -- the very organization the two men believe they have been stealing…
7
Run (1991)
★ 6/10
When a law student accidentally kills the son of a mob boss in a fight, he finds himself relentlessly pursued by the mob and the police.
8
Lights Out (2024)
★ 7.1/10
A drifting ex-soldier turns underground fighter with the help of a just-released ex-con, pitting him against corrupt cops and hired killers now gunning for him and all those he cares about.
9
Copshop (2021)
★ 6.3/10
On the run from a lethal assassin, a wily con artist devises a scheme to hide out inside a small-town police station. However, when the hit man turns up at the precinct, an unsuspecting rookie cop finds herself caught…
10
Run All Night (2015)
★ 6.4/10
Brooklyn mobster and prolific hit man Jimmy Conlon has seen better days. Longtime best friend of a mob boss, Jimmy is haunted by the sins of his past—as well as a dogged police detective who’s been one step behind…
11
The Departed (2006)
★ 8.2/10
To take down South Boston's Irish Mafia, the police send in one of their own to infiltrate the underworld, not realizing the syndicate has done likewise. While an undercover cop curries favor with the mob kingpin, a…
12
The Whole Nine Yards (2000)
★ 6.5/10
After a mobster agrees to cooperate with an FBI investigation in order to stay out of prison, he's relocated by the authorities to a life of suburban anonymity as part of a witness protection program. It's not long…
13
Cleaner (2025)
★ 6.6/10
When a group of radical activists take over an energy company's annual gala, seizing 300 hostages, an ex-soldier turned window cleaner suspended 50 storeys up on the outside of the building must save those trapped…
14
Sleepless (2017)
★ 5.9/10
Undercover Las Vegas police officer Vincent Downs, who has a lot of enemies, is caught in a high stakes web of corrupt cops and the mob-controlled casino underground. When a heist goes wrong, a crew of homicidal…
15
Shade (2003)
★ 6.2/10
Tiffany, Charlie and Vernon are con artists looking to up the ante from their typical scams. They figure a good way of doing this is taking down Dean "The Dean" Stevens, a well-known cardsharp, in a rigged game…
16
Raw Deal (1986)
★ 5.9/10
Mark Kaminsky is kicked out of the FBI for his rough treatment of a suspect. He winds up as the sheriff of a small town in North Carolina. FBI Chief Harry Shannon, whose son has been killed by a mobster named…
17
Johnny Dangerously (1984)
★ 6.3/10
An honest, goodhearted man is forced to turn to a life of crime to finance his neurotic mother's skyrocketing medical bills.
18
Triple 9 (2016)
★ 6/10
A gang of criminals and corrupt cops plan the murder of a police officer in order to pull off their biggest heist yet across town.
19
Blood Ties (2013)
★ 6.1/10
Two brothers, on either side of the law, face off over organized crime in Brooklyn during the 1970s.
20
Oscar (1991)
★ 6.4/10
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…