Movies Like Natural Born Heartbreakers

If you liked Natural Born Heartbreakers (2001), a movie directed by Professor Mike, 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
Casanova (2005)
★ 6.5/10
With a reputation for seducing members of the opposite sex, regardless of their marital status, a notorious womanizer discovers a beauty who seems impervious to his charms. However, as he continues to pursue the…
2
Mannequin (1987)
★ 6.9/10
Jonathan Switcher, an unemployed artist, finds a job as an assistant window dresser for a department store. When Jonathan happens upon a beautiful mannequin he previously designed, she springs to life and introduces…
3
Lady and the Tramp (1955)
★ 7.1/10
Lady, a golden cocker spaniel, meets up with a mongrel dog who calls himself the Tramp. He is obviously from the wrong side of town, but happenings at Lady's home make her decide to travel with him for a while.
4
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…
5
Dangerous Beauty (1998)
★ 7/10
Veronica is brilliant, gifted and beautiful, but the handsome aristocrat she loves, Marco Venier, cannot marry her because she is penniless and of questionable family. So Veronica's mother, Paola, teaches her to become…
6
One Night at McCool's (2001)
★ 5.9/10
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…
7
The Duchess and the Dirtwater Fox (1976)
★ 6.1/10
A female hustler is chasing after rich men, but becomes repeatedly mixed up with a suave con man and card shark through a series of misadventures before falling in love with him.
8
Two Moon Junction (1988)
★ 6.1/10
A young Southern débutante temporarily abandons her posh lifestyle and upcoming, semi-arranged marriage to have a lustful and erotic fling with a rugged drifter who works at a local carnival.
9
Sex and Death 101 (2007)
★ 6.2/10
A guy's life is turned around by an email, which includes the names of everyone he's had sex with and ever will have sex with. His situation gets worse when he encounters a femme fatale who targets men guilty of sex…
10
Operation Petticoat (1959)
★ 7.2/10
A World War II submarine commander finds himself stuck with a damaged sub, a con-man executive officer, and a group of army nurses.
11
The Importance of Being Earnest (2002)
★ 6.8/10
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
12
Love Potion No. 9 (1992)
★ 6.2/10
Unlucky in love, chemist Paul Matthews visits gypsy Madame Rosa for help. Quickly realizing he is a hopeless nerd, she gifts him with Love Potion No. 8, which makes anyone who wears it irresistible to the opposite sex…
13
Little Man (2006)
★ 5.9/10
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…
14
Being John Malkovich (1999)
★ 7.4/10
One day at work, unsuccessful puppeteer Craig finds a portal into the head of actor John Malkovich. The portal soon becomes a passion for anybody who enters its mad and controlling world of overtaking another human body.
15
June and John (2025)
★ 6.1/10
John leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his…
16
Bullets Over Broadway (1994)
★ 7.1/10
After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a…
17
A Street Cat Named Bob (2016)
★ 7.9/10
James Bowen, a homeless busker and recovering drug addict, has his life transformed when he meets a stray ginger cat.
18
Ziegfeld Girl (1941)
★ 6.6/10
Discovery by Flo Ziegfeld changes a girl's life but not necessarily for the better, as three beautiful women find out when they join the spectacle on Broadway: Susan, the singer who must leave behind her ageing…
19
Barefoot (2014)
★ 6.7/10
The "black sheep" son of a wealthy family meets a young psychiatric patient who's been raised in isolation her entire life. He takes the naive young woman home for his brother's wedding an improbable romance blooms, as…
20
Bad Boy Bubby (1993)
★ 6.9/10
Bubby has spent thirty years trapped in the same small room, tricked by his mother. One day, he manages to escape and, deranged and naive in equal measures, his adventure into a modern and nihilistic life begins.