Best movies like The Caddy

It's a screamer right down the fairway, FOOOOORE!!!!!!

A unique, carefully handpicked, selection of the best movies like The Caddy Starring Jerry Lewis, Dean Martin, Donna Reed, Barbara Bates, and more. If you liked The Caddy then you may also like: Vagabond Lady, Not So Dumb, The Optimists of Nine Elms, Overboard, Overboard and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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Vagabond Lady

Josephine Spiggins is thinking of marrying John Spear, the stuffed-shirt son of a department store owner. When John's free-spirit brother Tony returns from touring the South Seas in his boat, the "Vagabond Lady," Jo is attracted to him instead.

Not So Dumb

Not-so-smart chatterbox Dulcy Parker does and says all the wrong things, but they right themselves to prove she's not so dumb after all.

The Optimists of Nine Elms

A retired entertainer makes his living as a street musician on the streets of London. Two young children befriend the old musician, brightening his otherwise colorless life

Overboard

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 an opportunity to get even.

Overboard

A spoiled, wealthy yacht owner is thrown overboard and becomes the target of revenge from his mistreated employee.

Royal Wedding

Tom and Ellen are asked to perform as a dance team in England at the time of Princess Elizabeth's wedding. As brother and sister, each develops a British love interest, Ellen with Lord John Brindale and Tom with dancer Anne Ashmond.

Artists and Models

Painter Rick Todd is having difficulty with his career, so he starts taking inspiration from the dreams of his friend and roommate, Eugene, a comic book fan who narrates an adventure story while he sleeps. Unbeknown to Eugene, Abigail Parker, the artist for his favorite comic book, lives in the same building with her roommate, Bessie, the model for Abigail's drawings.

Bringing Up Baby

David Huxley is waiting to get a bone he needs for his museum collection. Through a series of strange circumstances, he meets Susan Vance, and the duo have a series of misadventures which include a leopard called Baby.

Caddyshack II

When a crass new-money tycoon's membership application is turned down at a snooty country club, he retaliates by buying the club and turning it into a tacky amusement park.

Captains Courageous

Harvey, the arrogant and spoiled son of an indulgent absentee-father, falls overboard from a transatlantic steamship and is rescued by a fishing vessel on the Grand Banks. Harvey fails to persuade them to take him ashore, nor convince the crew of his wealth. The captain offers him a low-paid job, until they return to port, as part of the crew that turns him into a mature, considerate young man.

Hero at Large

An idealistic but struggling actor finds his life unexpectedly complicated when he stops a robbery while wearing the costume of Captain Avenger, a superhero character of a film he is hired to to promote. He decides to dabble at being a superhero only to find that it is more difficult and dangerous than he ever imagined.

Sailor Beware

Meeting in a navy recruiting line, Al Crowthers and Melvin Jones become friends. Al has tried to enlist before, but was always rejected. He keeps trying so that he can impress women. Melvin, is allergic to women's cosmetics and his doctor prescribed ocean travel, so he decided to join the navy.

Stage Fright

A struggling actress tries to help a friend prove his innocence when he's accused of murdering the husband of a high-society entertainer.

The Legend of Bagger Vance

World War I has left golfer Rannulph Junuh a poker-playing alcoholic, his perfect swing gone. Now, however, he needs to get it back to play in a tournament to save the financially ravaged golf course of a long-ago sweetheart. Help arrives in the form of mysterious caddy Bagger Vance.

Harpoon

Rivalries, dark secrets, and sexual tension emerge when three best friends find themselves stranded on a yacht in the middle of the ocean under suspicious circumstances.

The Docks of New York

A blue-collar worker on New York's depressed waterfront finds his life changed after he saves a woman attempting suicide.

Free Willy 3: The Rescue

Willy the whale is back, this time threatened by illegal whalers making money off sushi. Jesse, now 16, has taken a job on an orca-researching ship, along with old friend Randolph and a sarcastic scientist, Drew. On the whaler's ship is captain John Wesley and his son, Max, who isn't really pleased about his father's job, but doesn't have the gut to say so. Along the way, Willy reunites with Jesse

Going Overboard

A struggling young comedian takes a menial job on a cruise ship where he hopes for his big chance to make it in the world of cruise ship comedy.

Happy Gilmore

Failed hockey player-turned-golf whiz Happy Gilmore -- whose unconventional approach and antics on the grass courts the ire of rival Shooter McGavin -- is determined to win a PGA tournament so he can save his granny's house with the prize money. Meanwhile, an attractive tour publicist tries to soften Happy's image.

Walk of Fame

A motley crew of aspiring performers come under the guidance of an eccentric and volatile acting coach.

The Big Broadcast of 1938

The Bellows family causes comic confusion on an ocean liner, with time out for radio-style musical acts.

Dangerous Crossing

A young bride is set to begin her honeymoon aboard a luxury liner. Her happiness does not last when she finds that her husband has disappeared. Trouble is, no one else ever saw him board the ship with her and his name has mysteriously dropped from the passenger list.

The Groomsmen

Blue-collar Paulie prepares for fatherhood and his forthcoming wedding to Sue by hanging out with his groomsmen. Brother Jimbo, cousin Mike, and his pals fill the reunion with drinking, boys-will-be-boys antics and a few unexpected personal confessions. But, when the bonding devolves into accusations and regret, Paulie has to decide whether he's ready to tie the knot and take this big step into adulthood.

Last Dance

Upon taking a new job, young lawyer Rick Hayes is assigned to the clemency case of Cindy Liggett, a woman convicted of first degree murder and sentenced to death. As Hayes investigates the background for her case, the two begin to form a deep friendship, while all the while the date for her execution draws nearer.

Tin Cup

A washed up golf pro working at a driving range tries to qualify for the US Open in order to win the heart of his succesful rival's girlfriend.

Triangle

When Jess sets sail on a yacht with a group of friends, she cannot shake the feeling that there is something wrong. Her suspicions are realized when the yacht hits a storm and the group is forced to board a passing ocean liner to get to safety, a ship Jess is convinced she’s been on before.

Black Point

In an Alaskan fishing town, a local crime boss suspects a local fisherman knows where his stolen money is, but this fisherman is no regular Joe.

Argentine Nights

An all-girl band flees to Argentina to avoid their creditors. Comedy with songs.

Where Hope Grows

Calvin Campbell is a former professional baseball player sent to an early retirement due to his panic attacks at the plate. Even though he had all the talent for the big leagues, he struggles with the curveballs life has thrown him. Today, he mindlessly sleepwalks through his days and the challenge of raising his teenager daughter. His life is in a slow downward spiral when it is suddenly awakened and invigorated by the most unlikely person – Produce, a young-man with Down syndrome who works at the local grocery store.

Let's Kill Ward's Wife

Everyone hates Ward’s wife and wants her dead, Ward most of all. But when his friends’ murderous fantasies turn into an (accidental) reality, they have to deal with a whole new set of problems — like how to dispose of the body and still make their 3 p.m. tee time.

Banning

A playboy golf pro, kicked off the circuit for alleged cheating, is forced to hustle for a living.

Calm at Sunset

Drama about a young man who defies his parents by dropping out of college to pursue his dream of owning a fishing boat, following in the footsteps of his father and grandfather.

He's My Guy

The former members of a vaudeville team meet up again in a defense plant during WW II.

Jackass Presents: Bad Grandpa .5

Bad Grandpa .5 gives you a whole new perspective on the world of Irving Zisman with bonus scenes and pranks also featuring Spike Jonze as "Gloria" and Catherine Keener as Irving's wife "Ellie", plus a look at the evolution of Johnny Knoxville's naughty alter-ego, the makeup effects, and a behind-the-scenes peek at the idiocy it takes to make a hidden camera movie in public.

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