Movies Like Brewster's Millions

If you liked Brewster's Millions (1921), a comedy movie directed by Joseph Henabery, 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
The Family Jewels (1965)
★ 6.5/10Also comedy
A young heiress must choose between six uncles, one of which is up to no good and out to harm the girl's beloved bodyguard who practically raised her.
2
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
3
Peter Rabbit 2: The Runaway (2021)
★ 7/10Also comedy
Peter Rabbit runs away from his human family when he learns they are going to portray him in a bad light in their book. Soon, he crosses paths with an older rabbit who ropes him into a heist.
4
Brewster's Millions (1985)
★ 6.6/10Also comedy
Monty Brewster, an aging minor-league baseball player, stands to inherit $300 million if he can successfully spend $30 million in 30 days without anything to show for it, and without telling anyone what he's up to... A…
5
Lemony Snicket's A Series of Unfortunate Events (2004)
★ 6.8/10Also comedy
Three wealthy children's parents are killed in a fire. When they are sent to a distant relative, they find out that he is plotting to kill them and seize their fortune.
6
LEGO Marvel Avengers: Mission Demolition (2024)
★ 6.5/10Also comedy
A young, aspiring hero and superhero fan inadvertently unleashes a powerful new villain looking to rid the world of the Avengers.
7
Dennis the Menace (1993)
★ 5.9/10Also comedy
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
8
Blank Check (1994)
★ 6/10Also comedy
Bullied by his siblings and nagged by his parents, 11-year-old Preston Waters is fed up with his family — especially their frugality. But he gets his chance to teach them a lesson when a money-laundering criminal…
9
Monster Family 2 (2021)
★ 6.6/10Also comedy
To free Baba Yaga and Renfield from the clutches of Monster Hunter Mila Starr, the Wishbone Family once more transforms into a Vampire, Frankenstein's Monster, a Mummy and a Werewolf but when aided by their three pet…
10
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
11
How to Eat Fried Worms (2006)
★ 6.2/10Also comedy
During the first day of his new school year, a fifth grade boy squares off against a bully and winds up accepting a dare that could change the balance of power within the class.
12
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedy
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…
13
The Sandlot 2 (2005)
★ 5.9/10Also comedy
A decade has passed in the small town where the original Sandlot gang banded together during the summer of ’62 to play baseball and battle the Beast. Now, back at the dugout, nine new kids descend on the diamond only…
14
Diary of a Wimpy Kid: Rodrick Rules (2011)
★ 6.7/10Also comedy
Wimpy Greg Heffley, now in seventh grade, thinks he has it all together. He has mastered middle school and gotten rid of the Cheese Touch. However, Greg's older brother, Rodrick, is itching to cut him down to size. He…
15
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
16
The Luck of the Irish (2001)
★ 6.1/10Also comedy
A teenager must battle for a gold charm to keep his family from being controlled by an evil leprechaun.
17
Ri¢hie Ri¢h (1994)
★ 6/10Also comedy
Billionaire heir Richie Rich has it all, including Reggie Jackson as a batting coach and Claudia Schiffer as a personal trainer -- but no playmates. What's more, scoundrel Laurence Van Dough is scheming to take over…
18
The Air Up There (1994)
★ 6.1/10Also comedy
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…
19
Johnny English Strikes Again (2018)
★ 6.3/10Also comedy
Disaster strikes when a criminal mastermind reveals the identities of all active undercover agents in Britain. The secret service can now rely on only one man - Johnny English. Currently teaching at a minor prep…
20
Are We Done Yet? (2007)
★ 5.8/10Also comedy
Newlyweds Nick and Suzanne decide to move to the suburbs to provide a better life for their two kids. But their idea of a dream home is disturbed by a contractor with a bizarre approach to business.