Movies Like Caddyshack II
If you loved Caddyshack II's Comedy storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
Tom Segura: Disgraceful
Tom Segura gives voice to the sordid thoughts you'd never say out loud, with blunt musings on porn, parking lot power struggles, parenthood and more.
The Air Up There
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home movie. But Saleh is the chief's son and has responsibilities at home, since the tribe's land is threatened by a mining company with its own hotshot basketball team.
Easy Money
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.
Thunderstruck
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Eddie Murphy Raw
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
Almost Friends
A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a serious boyfriend. As they become closer, the line between friendship and intimacy is blurred, and the situation forces both to examine where they are in their lives.
The Little Rascals Save the Day
When the Little Rascals are unable to raise enough money to save their grandma's bakery from shutting down, their only hope is to win a local talent show and use the prize money to save the shop.
Dave Chappelle: The Unstoppable...
Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.
More Movies Like Caddyshack II
American Dreamer
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
Wicked Little Letters
When the denizens of Littlehampton – including conservative Edith – begin receiving letters full of hilarious profanities, rowdy Irish migrant Rose is charged with the crime. Suspecting something amiss, the town's women band together to investigate.
Marc Maron: End Times Fun
Marc Maron wades through a swamp of vitamin hustlers, evangelicals and grown male nerd children, culminating in a gleefully filthy end-times fantasy.
Brain Donors
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.
Rookie of the Year
12-year-old Henry Rowengartner, whose late father was a minor league baseball player, grew up dreaming of playing baseball, despite his physical shortcomings. After Henry's arm is broken while trying to catch a baseball at school, the tendon in that arm heals too tightly, allowing Henry to throw pitches that are as fast as 103 mph. Henry is spotted at nearby Wrigley Field by Larry "Fish" Fisher, the general manager of the struggling Chicago Cubs, after Henry throws an opponent's home-run ball all the way from the outfield bleachers back to the catcher, and it seems that Henry may be the pitcher that team owner Bob Carson has been praying for.
Mr. Bones
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
29th Street
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
Watching the Detectives
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 turned upside down and the line between reality and the movies quickly begins to blur.
Class
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.
Landline
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
The F**k-It List
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
Why These Movies Are Similar
These recommendations share core qualities with Caddyshack II (1988): Comedy themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Caddyshack II.
See full details for Caddyshack II (1988)