Movies Like Once Upon a Madonna

If you liked Once Upon a Madonna (1985), a movie directed by Michael Phillips, 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
Original Sin (2001)
★ 6.2/10
A young man is plunged into a life of subterfuge, deceit and mistaken identity in pursuit of a femme fatale whose heart is never quite within his grasp.
2
You Can't Take It with You (1938)
★ 7.5/10
Alice, the only relatively normal member of the eccentric Sycamore family, falls in love with Tony Kirby, but his wealthy banker father and snobbish mother strongly disapprove of the match. When the Kirbys are invited…
3
The Twelve Chairs (1970)
★ 6.2/10
In 1920s Soviet Russia, a fallen aristocrat, a priest and a con artist search for a treasure of jewels hidden inside one of twelve dining chairs, lost during the revolution.
4
The Lady Eve (1941)
★ 7.3/10
It's no accident when wealthy Charles falls for Jean. Jean is a con artist with her sights set on Charles' fortune. Matters complicate when Jean starts falling for her mark. When Charles suspects Jean is a gold digger…
5
The Brass Teapot (2012)
★ 6.1/10
When a couple discovers that a brass teapot makes them money whenever they hurt themselves, they must come to terms with how far they are willing to go.
6
Heatwave (2022)
★ 6.2/10
A woman's life takes an unexpected turn when she falls for her boss's wife. She must soon defend herself as she becomes entangled in a web of malice.
7
The Portrait of a Lady (1996)
★ 5.9/10
Ms. Isabel Archer isn't afraid to challenge societal norms. Impressed by her free spirit, her kindhearted cousin writes her into his fatally ill father's will. Suddenly rich and independent, Isabelle ventures into the…
8
When in Rome (2010)
★ 5.9/10
Disillusioned with romance, Beth, an ambitious New Yorker, travels to Rome for her sister's wedding, where she plucks magic coins from a special fountain of love. The coins attract unwanted attention from an assortment…
9
Ballad of a Small Player (2025)
★ 5.8/10
Amid the glittering casinos of Macau, a gambler running from his past—and his debts—becomes fascinated by an enigmatic woman at the baccarat table.
10
Overboard (1987)
★ 6.9/10
Heiress Joanna Stayton hires carpenter Dean Proffitt to build a closet on her yacht—and refuses to pay him for the project when it's done. But after Joanna accidentally falls overboard and loses her memory, Dean sees…
11
The Good Liar (2019)
★ 6.7/10
Career con man Roy sets his sights on his latest mark: recently widowed Betty, worth millions. And he means to take it all. But as the two draw closer, what should have been another simple swindle takes on the ultimate…
12
Watching the Detectives (2007)
★ 6.3/10
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets…
13
Erin Brockovich (2000)
★ 7.4/10
A twice-divorced mother of three who sees an injustice, takes on the bad guy and wins -- with a little help from her push-up bra. Erin goes to work for an attorney and comes across medical records describing illnesses…
14
The Adjustment Bureau (2011)
★ 6.8/10
A man glimpses the future Fate has planned for him – and chooses to fight for his own destiny. Battling the powerful Adjustment Bureau across, under and through the streets of New York, he risks his destined greatness…
15
Falling for Christmas (2022)
★ 6.2/10
An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.
16
Great Expectations (2012)
★ 6.4/10
Orphan Pip discovers through lawyer Mr. Jaggers that a mysterious benefactor wishes to ensure that he becomes a gentleman. Reunited with his childhood patron, Miss Havisham, and his first love, the beautiful but…
17
Gentlemen Prefer Blondes (1953)
★ 7.3/10
Lorelei Lee is a beautiful showgirl engaged to be married to the wealthy Gus Esmond, much to the disapproval of Gus' rich father, Esmond Sr., who thinks that Lorelei is just after his money. When Lorelei goes on a…
18
The Last Seduction (1994)
★ 6.7/10
A devious femme fatale steals her husband’s drug money and hides out in a small town where she meets the perfect dupe for her next scheme.
19
Godmothered (2020)
★ 6.7/10
A young and unskilled fairy godmother that ventures out on her own to prove her worth by tracking down a young girl whose request for help was ignored. What she discovers is that the girl has now become a grown woman…
20
A Nice Girl Like You (2020)
★ 5.8/10
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…