Movies Like Hangin' with the Homeboys

If you liked Hangin' with the Homeboys (1991), a comedy and drama movie directed by Joseph B. Vasquez, 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
House of Strangers (1949)
★ 7/10Also drama
Ruthless Italian-American banker Gino Monetti is engaged in a number of criminal activities. Three of his four grown sons refuse to help their father stay out of prison after he's arrested for his questionable business…
2
The Brink's Job (1978)
★ 6.2/10Also comedy and drama
In 1950, a group of unlikely criminal masterminds commits the robbery of the century. Led by Tony Pino, a petty thief fresh out of prison, and Joe McGinnis, who specializes in planning lucrative capers, the gang robs…
3
The Trip to Italy (2014)
★ 6.4/10Also comedy and drama
Years after their successful restaurant review tour of Northern England, Steve Coogan and Rob Brydon are commissioned for a new tour in Italy.
4
Analyze This (1999)
★ 6.5/10Also comedy
Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family,"…
5
SubUrbia (1997)
★ 6.2/10Also comedy and drama
A group of suburban teenagers try to support each other through the difficult task of becoming adults.
6
Manhattan Murder Mystery (1993)
★ 7.3/10Also comedy
A middle-aged couple suspects foul play when their neighbor's wife suddenly drops dead.
7
Paper Man (2009)
★ 6.3/10Also comedy and drama
A coming-of-middle-age comedy that chronicles the unlikely friendship between failed author Richard Dunne and a Long Island teen who teaches him a thing or two about growing up, all under the disapproving eye of his…
8
Paradise Alley (1978)
★ 5.9/10Also drama
Three Italian-American brothers, living in the slums of 1940's New York City, try to help each other with one's wrestling career using one brother's promotional skills and another brother's con-artist tactics to thwart…
9
White Chicks (2004)
★ 7/10Also comedy
Two FBI agent brothers, Marcus and Kevin Copeland, accidentally foil a drug bust. To avoid being fired they accept a mission escorting a pair of socialites to the Hamptons--but when the girls are disfigured in a car…
10
Please Give (2010)
★ 6.2/10Also comedy and drama
In New York City, a husband and wife butt heads with the granddaughters of the elderly woman who lives in the apartment the couple owns.
11
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
12
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
13
City Island (2009)
★ 6.9/10Also drama and comedy
The Rizzos, a family who doesn't share their habits, aspirations, and careers with one another, find their delicate web of lies disturbed by the arrival of a young ex-con brought home by Vince, the patriarch of the…
14
Things Change (1988)
★ 6.2/10Also comedy and drama
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…
15
Welcome to Collinwood (2002)
★ 6.1/10Also comedy
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
16
Brigsby Bear (2017)
★ 7.1/10Also comedy and drama
Brigsby Bear Adventures is a children's TV show produced for an audience of one: James. When the show abruptly ends, James's life changes forever, and he sets out to finish the story himself.
17
Keeping Up with the Joneses (2016)
★ 6.1/10Also comedy
An ordinary suburban couple finds it’s not easy keeping up with the Joneses – their impossibly gorgeous and ultra-sophisticated new neighbors – especially when they discover that Mr. and Mrs. “Jones” are covert…
18
Eleanor the Great (2025)
★ 6.8/10Also drama
94-year-old Eleanor Morgenstein tries to rebuild her life after the death of her best friend. As a result, she moves back to New York City after living in Florida for decades.
19
Made in Italy (2020)
★ 6/10Also comedy and drama
A bohemian artist travels from London to Italy with his estranged son to sell the house they inherited from his late wife.
20
Chloe and Theo (2015)
★ 5.9/10Also comedy and drama
A young woman, Chloe, living by her wits on the streets of New York City, has a chance meeting with a wise Inuit Eskimo, Theo, who was sent to New York by his elders to provide a message to the people of the world – We…