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Movies Like Playing For Keeps
Find movies like Playing For Keeps (2001) using TMDB similarity plus Movie Rankings community context. Our top current pick is Born Yesterday. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.
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Born Yesterday
1950
Uncouth, loud-mouth junkyard tycoon Harry Brock descends upon Washington D.C. to buy himself a congressman or two, bringing with him his mistress, ex-showgirl Billie Dawn.

Pillow Talk
1959
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a complaint against him, Brad sets about to seduce her in the guise of a sincere and upstanding Texas rancher. When mutual friend Jonathan discovers that his best friend is moving in on the girl he desires, however, sparks fly.

How to Make a Killing
2026
Disowned at birth by his obscenely wealthy family, blue-collar Becket Redfellow will stop at nothing to reclaim his inheritance, no matter how many relatives stand in his way.

After Ever Happy
2022
As a shocking truth about a couple's families emerges, the two lovers discover they are not so different from each other. Tessa is no longer the sweet, simple, good girl she was when she met Hardin — any more than he is the cruel, moody boy she fell so hard for.

There's Something About Mary
1998
For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her.

Everything You Always Wanted to Know About Sex *But Were Afraid to Ask
1972
A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and a journalist adventure through lab experiments and game shows, all seeking answers to common questions that many would never ask.

The Cocoanuts
1929
During the Florida land boom, the Marx Brothers run a hotel, auction off some land and thwart a jewel robbery.

That Touch of Mink
1962
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a suitable match for his boss. Despite their mutual attraction, Cathy and Philip want different things. Philip wants a fling, while Cathy wants a marriage. As they travel to exotic locales, their differing motivations are put to the test.

The Honey Pot
1967
In Venice, a millionaire hires an actor to help him prank three greedy exes into thinking he's dying and leaving his fortune to one of them.

The Grass Is Greener
1960
Victor and Hillary are down on their luck to the point that they allow tourists to take guided tours of their castle. But Charles Delacro, a millionaire oil tycoon, visits, and takes a liking to more than the house. Soon, Hattie Durant gets involved and they have a good old fashioned love triangle.

La Dolce Villa
2025
When his daughter decides to buy a crumbling Tuscan villa, Eric rushes to Italy to talk her out of it — and instead finds beauty, romance and new purpose.

Pocket Listing
2016
A satirical thriller about L.A.'s real estate roller coaster. Double crosses, adultery, murder, mistaken identity, and revenge ensues when a mysterious power player and his sultry wife hire a disgraced Los Angeles property broker to discreetly market and sell their Malibu villa.

Delivery Man
2013
An affable underachiever finds out he's fathered 533 children through anonymous donations to a fertility clinic 20 years ago. Now he must decide whether or not to come forward when 142 of them file a lawsuit to reveal his identity.

Brain Donors
1992
Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit the rich widow and her scheming big-shot lawyer, who also wants to run the ballet.

Fairy Tales
1978
On his twenty-first birthday, the Prince goes on a quest that takes him across the land searching for the one woman that gets him sexually excited, Princess Sleeping Beauty.

The Distinguished Gentleman
1992
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows from lobbyists.

Easy Money
1983
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.

Intolerable Cruelty
2003
A revenge-seeking gold digger marries a womanizing Beverly Hills lawyer with the intention of making a killing in the divorce.
What are the best movies like Playing For Keeps?
Born Yesterday is the strongest current recommendation on this page for viewers looking for movies like Playing For Keeps.
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