Movies Like It's Fun to Gamble, If You Win

If you liked It's Fun to Gamble, If You Win, a comedy movie directed by Wendy Chandra, 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
Easy Money (1983)
★ 6/10Also comedy
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.
2
Let It Ride (1989)
★ 6.3/10Also comedy
An average kind of guy who has a slight problem with gambling goes to the track, and mystically, it seems as though he can't lose, no matter how he bets; and he has an incredible day.
3
The Wonderful Story of Henry Sugar (2023)
★ 7.3/10Also comedy
A rich man learns about a guru who can see without using his eyes. He sets out to master the skill in order to cheat at gambling.
4
Vegas Vacation (1997)
★ 6/10Also comedy
The Griswold family hits the road again for a typically ill-fated vacation, this time to the glitzy mecca of slots and showgirls—Las Vegas.
5
Room Service (1938)
★ 6.5/10Also comedy
Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
6
A Bad Moms Christmas (2017)
★ 6.3/10Also comedy
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
7
Dirty Work (1998)
★ 6.2/10Also comedy
Unemployed and recently dumped, Mitch and his buddy Sam start a revenge-for-hire business to raise the $50,000 that Sam's father needs to get a heart transplant.
8
Analyze That (2002)
★ 5.8/10Also comedy
The mafia's Paul Vitti is back in prison and will need some serious counseling when he gets out. Naturally, he returns to his analyst Dr. Ben Sobel for help and finds that Sobel needs some serious help himself as he…
9
Get Shorty (1995)
★ 6.5/10Also comedy
Chili Palmer is a Miami mobster who gets sent to L.A. to collect a bad debt from Harry Zimm, a Hollywood producer who specializes in cheesy horror films. When Chili meets Harry's leading lady, the romantic sparks fly…
10
Quiz Lady (2023)
★ 6.7/10Also comedy
A brilliant but tightly wound, gameshow-obsessed young woman, Anne, and her estranged, train-wreck of a sister, Jenny, must work together to help cover their mother's gambling debts. When Anne's beloved dog is…
11
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
12
Sgt. Bilko (1996)
★ 5.9/10Also comedy
The US army is known for churning out lean mean fighting machines intent on protecting our great nation. Sergeant Ernie Bilko is the leader of a ragtag group of the sorriest soldiers ever to enlist in the armed forces.
13
Dirty Rotten Scoundrels (1988)
★ 7.1/10Also comedy
Con artist Lawrence Jamieson is a longtime resident of a luxurious coastal resort, where he enjoys the lavish fruits of his deceptions -- that is, until a competitor, Freddy Benson, shows up. When the new guy's lowbrow…
14
Ca$h (2010)
★ 5.9/10Also comedy
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a…
15
Grandma's Boy (2006)
★ 6.5/10Also comedy
Even though he's 35, Alex acts more like he's 13, spending his days as the world's oldest video game tester and his evenings developing the next big Xbox game. But when he gets kicked out of his apartment, he's forced…
16
The Hangover Part III (2013)
★ 6.2/10Also comedy
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
17
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
18
Horrible Bosses 2 (2014)
★ 6.2/10Also comedy
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
19
Four Rooms (1995)
★ 5.9/10Also comedy
It's Ted the Bellhop's first night on the job...and the hotel's very unusual guests are about to place him in some outrageous predicaments. It seems that this evening's room service is serving up one unbelievable…
20
Death at a Funeral (2010)
★ 5.9/10Also comedy
Aaron's father's funeral is today at the family home, and everything goes wrong: the funeral home delivers the wrong body, his cousin accidentally drugs her fiancé, and Aaron's successful younger brother, Ryan, flies…