Movies like Chasing Oscar (2019)
The best movies like Chasing Oscar (2019) are Fun with Dick and Jane (1977), 68 Kill (2017) and One Night at McCool's (2001). If Chasing Oscar hooked you with its comedy and crime, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedTrap House (2025)6.6/10 from 333 votes
- NewestSimpsley (2026)Released 2026
Fun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like this68 Kill (2017)
Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000.
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisOne Night at McCool's (2001)
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...
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisSheroes (2023)
When four thick-as-thieves friends arrive in Thailand, they quickly find themselves in over their heads. Fighting to stay alive, they employ their unique set of skills and unleash their fierce loyalty in a heart-pumping battle for survival.
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisSimpsley (2026)
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment: Skinner's clingy, dim-witted mooch of a houseguest, Homer Simpsley. Lies, lust and Italian lira are abound.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Absolute CinemaMovies like thisThe Pickup (2025)
A routine cash pickup takes a wild turn when mismatched armored truck drivers Russell and Travis are ambushed by ruthless criminals led by savvy mastermind Zoe.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisAccident Man (2018)
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
Why it matches: Recommended by TMDB viewers · both crime & comedy
Popcorn FlickMovies like thisThe Dream Team (1989)
Four mental patients on a field trip in New York City must save their caring chaperone, who ends up being taken to a hospital in a coma after accidentally witnessing a murder, before the killers can find him and finish the job.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisCotton Comes to Harlem (1970)
Harlem's African-American population is being ripped off by the Rev. Deke O'Malley, who dishonestly claims that small donations will secure parcels of land in Africa. When New York City police officers Gravedigger Jones and Coffin Ed Johnson look into O'Malley's scam, they learn that the cash is being smuggled inside a bale of cotton. However, the police, O'Malley, and lots of others find themselves scrambling when the money goes missing.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisMarried to the Mob (1988)
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisWho Is Cletis Tout? (2001)
With a hitman’s gun aimed at him, Finch tells the story of how he broke out of jail, fell in love, and took the identity of a man wanted by the Mafia.
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisTrailer Park Boys: Countdown to Liquor Day (2009)
Ricky, Julian and Bubbles are about to get out of jail, and this time, Julian vows to go straight, even open a legit business. Soon the Boys will all be rich. At least that's what they've told the parole board. But when they arrive back at the park, they find it's not the same old Sunnyvale - and it's not the same old Jim Lahey, Trailer Park Supervisor.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisThe Adventures of Ford Fairlane (1990)
To the Los Angeles elite, Ford Fairlane is known as "Mr. Rock 'n' Roll Detective." This loudmouthed ladies' man serves an exclusive rock star clientele, who depend on his keen eye and smug discretion. So when a heavy-metal musician dies mid-concert, Fairlane is on the case before the lights come up. But things turn shocking when radio personality Johnny Crunch hires Fairlane to find a missing groupie mere hours before he is electrocuted live on air.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisMystery Team (2009)
A group of former Encyclopedia Brown-style child-detectives struggle to solve an adult mystery.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisTrap House (2025)
An undercover DEA agent and his partner embark on a game of cat and mouse with an audacious, and surprising group of thieves – their own rebellious teenagers, who have begun robbing from a dangerous cartel, using their parents' tactics and top-secret intel to do it.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisMisdirection (2026)
A desperate couple have pulled off a string of high-end break-ins to pay off a mob debt. When they attempt to rob their latest victim, they find themselves caught in a deadly game of cat and mouse. The tables are turned and the hunters become the hunted.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisThe Protector (1985)
Billy Wong is a New York City cop whose partner is gunned down during a robbery. Billy and his new partner, Danny Garoni, are working security at a fashion show when a wealthy man's daughter, Laura Shapiro, is kidnapped. The Federal authorities suspect that Laura's father is involved with Mr. Ko, a Hong Kong drug kingpin, so the NYC police commissioner sends the two cops to Hong Kong to investigate.
Why it matches: Recommended by TMDB viewers · both crime
SnoozefestMovies like thisWire Room (2022)
New recruit Justin Rosa must monitor arms-smuggling cartel member Eddie Flynn — and keep him alive at all costs. When a SWAT team descends on Flynn’s home, Rosa breaks protocol and contacts the gangster directly to save his life. As gunmen break into the Wire Room and chaos erupts, Mueller and Rosa make a final, desperate stand against the corrupt agents and officials who seek to destroy evidence and kill them both.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisAbsolution (2024)
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. He is determined to leave a positive legacy for his grandson, but the criminal underworld isn’t done with him and won’t loosen their grip willingly.
Why it matches: Recommended by TMDB viewers · both crime
SnoozefestMovies like thisFight or Flight (2025)
A mercenary takes on the job of tracking down a target on a plane but must protect that target when they're surrounded by people trying to kill both of them.
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like Chasing Oscar?
The closest matches to Chasing Oscar are Fun with Dick and Jane (1977), 68 Kill (2017) and One Night at McCool's (2001). Below are 17 more, each with the reason it matches.
What should I watch after Chasing Oscar?
Start with Fun with Dick and Jane (1977), the closest match to Chasing Oscar.
What is the highest-rated movie like Chasing Oscar?
Trap House (2025), rated 6.6/10 by 333 TMDB users.
What is the newest movie like Chasing Oscar?
Simpsley (2026) is the most recent release on this list.
Are there English movies like Chasing Oscar?
Yes: Fun with Dick and Jane (1977), 68 Kill (2017) and One Night at McCool's (2001).
How are movies similar to Chasing Oscar chosen?
First come films that Trakt’s viewers watch alongside Chasing Oscar, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.