Movies Like Flirting with Disaster

If you liked Flirting with Disaster (1996), a comedy movie directed by David O. Russell, 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 Hangover Part III (2013)
★ 6.2/10Also comedy
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
2
Joy Ride (2023)
★ 6.5/10Also comedy
When Audrey's business trip to Asia goes sideways, she enlists the aid of Lolo, her irreverent, childhood best friend who also happens to be a hot mess; Kat, her college friend turned Chinese soap star; and Deadeye…
3
The Wrecking Crew (2026)
★ 7.1/10Also comedy
Estranged half-brothers Jonny and James reunite after their father's mysterious death. As they search for the truth, buried secrets reveal a conspiracy threatening to tear their family apart.
4
I Love My Dad (2022)
★ 5.9/10Also comedy
A hopelessly estranged father catfishes his son in an attempt to reconnect.
5
Sisters (2015)
★ 6/10Also comedy
Two disconnected sisters are summoned to clean out their childhood bedrooms before their parents sell their family home.
6
Eenie Meanie (2025)
★ 6.3/10Also comedy
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
7
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
8
Balls Up (2026)
★ 5.8/10Also comedy
Two marketing executives go "balls out" and pitch a bold full‑coverage condom sponsorship with the World Cup. After their drunken celebration in Brazil sparks a global scandal, they must outrun furious fans, criminals…
9
Little Brother (2026)
★ 6.4/10Also comedy
A tightly wound realtor's picture-perfect life gets an extreme makeover when his lovably chaotic "little brother" suddenly reappears.
10
Little Man (2006)
★ 5.9/10Also comedy
After leaving prison, dwarf criminal Calvin Sims joins his moron brother Percy in stealing an expensive huge diamond from a jewelry store for the mobster Walken. They are chased by the police, and Calvin hides the…
11
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
12
Leaves of Grass (2009)
★ 6/10Also comedy
An Ivy League professor returns home, where his pot-growing twin brother has concocted a plan to take down a local drug lord.
13
The Unbearable Weight of Massive Talent (2022)
★ 6.8/10Also comedy
Creatively unfulfilled and facing financial ruin, Nick Cage must accept a $1 million offer to attend the birthday of a dangerous superfan. Things take a wildly unexpected turn when Cage is recruited by a CIA operative…
14
Harold & Kumar Go to White Castle (2004)
★ 6.6/10Also comedy
Nerdy accountant Harold and his irrepressible friend, Kumar, get stoned watching television and find themselves utterly bewitched by a commercial for White Castle. Convinced there must be one nearby, the two set out on…
15
The Pope of Greenwich Village (1984)
★ 6.4/10Also comedy
Charlie and his troublesome cousin Paulie decide to steal $150,000 in order to back a "sure thing" race horse that Paulie has inside information on. The aftermath of the robbery gets them into serious trouble with the…
16
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
17
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
18
Brothers (2024)
★ 5.9/10Also comedy
A reformed criminal's attempt at going straight is derailed when he reunites with his sanity-testing twin brother on a road trip for the score of a lifetime. Dodging bullets, the law, and an overbearing mother along…
19
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
20
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…