Movies Like The Worst Possible Time

If you liked The Worst Possible Time (2019), a movie directed by Scott Sawitz, 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
The Midnight Patrol (1933)
★ 6.6/10
Novice policemen Stan and Ollie bungle a burglary investigation.
2
Home Alone 2: Lost in New York (1992)
★ 6.8/10
Instead of flying to Florida with his folks, Kevin ends up alone in New York, where he gets a hotel room with his dad's credit card—despite problems from a clerk and meddling bellboy. But when Kevin runs into his old…
3
Mr. Monk's Last Case: A Monk Movie (2023)
★ 6.8/10
Monk steps out of retirement as his stepdaughter's wedding turns tragic when her fiancé dies in a bungee jumping accident.
4
Intrusion (2021)
★ 6/10
When a husband and wife move to a small town, a home invasion leaves the wife traumatized and suspicious that those around her might not be who they seem.
5
Samaritan (2022)
★ 6.6/10
Thirteen year old Sam Cleary suspects that his mysteriously reclusive neighbor Mr. Smith is actually the legendary vigilante Samaritan, who was reported dead 25 years ago. With crime on the rise and the city on the…
6
Plunder Road (1957)
★ 6.9/10
A spectacular heist starts to unravel as the crooks take it on the lam.
7
Safe House (2025)
★ 6.4/10
Trapped in a high-security safe house after a terrorist attack in downtown Los Angeles, six government agents realize they must survive not just the enemy outside, but the potential traitor among them.
8
The Asphalt Jungle (1950)
★ 7.5/10
Recently paroled from prison, legendary burglar "Doc" Riedenschneider, with funding from Alonzo Emmerich, a crooked lawyer, gathers a small group of veteran criminals together in the Midwest for a big jewel heist.
9
Legend of the White Dragon (2026)
★ 6.5/10
Forced to hide in the shadows, fugitive hero Erik Reed must clear his name to reunite with his family. Standing in his way is a mysterious villain obsessed with destroying the White Dragon for good.
10
The Substitute 2: School's Out (1998)
★ 6.5/10
When teacher Randall Thomasson is killed during a carjacking, an unexpected visitor shows up at his funeral - his estranged brother, Karl Thomasson. An ex-Green Beret turned mercenary, Karl signs on as a new substitute…
11
Defendor (2009)
★ 6.4/10
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…
12
GirlHouse (2014)
★ 6/10
In an attempt to make some extra cash while away at College, Kylie moves into a house that streams content to an X-rated website. After a deranged fan hacks in to determine the house's location, she finds herself in a…
13
The Bad Guys: Haunted Heist (2024)
★ 6.8/10
The crafty Bad Guys crew embarks on a high-stakes Halloween heist to swipe a priceless amulet from a spooky mansion. What could go wrong?
14
Bagman (2024)
★ 6.1/10
For centuries and across cultures, parents have warned their children of the legendary Bagman, who snatches innocent children and stuffs them into his vile, rotting bag—never to be seen again. Patrick McKee narrowly…
15
The Paper Tigers (2020)
★ 6.7/10
Three middle aged men polish their martial arts skills to avenge their fallen master.
16
The Forger (2014)
★ 5.8/10
A former child art prodigy and second generation petty thief arranges to buy his way out of prison to spend time with his ailing son, only to be forced to alter his plans and commit one more job for the man who…
17
Pacific Heights (1990)
★ 6.3/10
A couple works hard to renovate their dream house and become landlords to pay for it. Unfortunately one of their tenants has plans of his own.
18
The Nice Guys (2016)
★ 7.1/10
A private eye investigates the apparent suicide of a fading porn star in 1970s Los Angeles and uncovers a conspiracy.
19
Sexy Beast (2001)
★ 7/10
Ex-safecracker Gal Dove has served his time behind bars and is blissfully retired to a Spanish villa paradise with a wife he adores. The idyll is shattered by the arrival of his nemesis Don Logan, intent on persuading…
20
The Collector (2009)
★ 6.6/10
Desperate to repay his debt to his ex-wife, an ex-con plots a heist at his new employer's country home, unaware that a second criminal has also targeted the property, and rigged it with a series of deadly traps.