Most Similar Movies to Caddyshack II (1988)
If you are looking for movies like Caddyshack II (1988), you might like movies tagged with keyword : tycoon, golfer, daughter, mercenary, wealthy man, attorney, madcap, hilarious, country club, amusement park, golf course, golf, class distinctions, snobbishness, anti-semitism, real estate, assassination attempt, underdog, wretched excess, rivalry, 1980s .
Aquamarine (2006), The Bad News Bears (1976), Pretty in Pink (1986), My Best Friend's Wedding (1997), Bad News Bears (2005), Racing Stripes (2005), Happy Gilmore (1996) ... Let's take a look at the following list...

Aquamarine (2006)
Two teenage girls discover a mermaid in their beach club's swimming pool.
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The Bad News Bears (1976)
An aging, down-on-his-luck ex-minor leaguer coaches a team of misfits in an ultra-competitive California little league.
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Pretty in Pink (1986)
A poor girl must choose between the affections of dating her childhood sweetheart or a rich but sensitive playboy.
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My Best Friend's Wedding (1997)
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.
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Bad News Bears (2005)
A grizzled little league coach tries to turn his team of misfits into champs.
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Racing Stripes (2005)
An abandoned zebra grows up believing he is a racehorse, and, with the help of his barnyard friends and a teenage girl, sets out to achieve his dream of racing with thoroughbreds.
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Happy Gilmore (1996)
A rejected hockey player puts his skills to the golf course to save his grandmother's house.
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Bridesmaids (2011)
Competition between the maid of honor and a bridesmaid, over who is the bride's best friend, threatens to upend the life of an out-of-work pastry chef.
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The Little Rascals (1994)
Alfalfa is wooing Darla and his "He-Man-Woman-Hating" friends attempt to sabotage the relationship.
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D2: The Mighty Ducks (1994)
Can Gordon's team win the Junior Goodwill Games in California in spite of all the set-backs?
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Angels in the Outfield (1994)
When a boy prays for a chance to have a family if the California Angels win the pennant, angels are assigned to make that possible.
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Made of Honor (2008)
A guy in love with an engaged woman tries to win her over after she asks him to be her maid of honor.
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The Intouchables (2011)
After he becomes a quadriplegic from a paragliding accident, an aristocrat hires a young man from the projects to be his caregiver.
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Play It to the Bone (1999)
Two best friends and former middleweight contenders travel to Las Vegas to fight each other for the first time.
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Lage Raho Munna Bhai (2006)
Munna Bhai embarks on a journey with Mahatma Gandhi in order to fight against a corrupt property dealer.
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Deck the Halls (2006)
Two neighbors have it out after one of them decorates his house for the holidays so brightly that it can be seen from space.
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Herbie Fully Loaded (2005)
Maggie Peyton, the new owner of Herbie, Number 53, the free-wheelin' Volkswagen bug with a mind of its own, puts the car through its paces on the road to becoming a NASCAR competitor.
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When Harry Met Sally... (1989)
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
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