Movies Like Freddy and the Millionaire

If you liked Freddy and the Millionaire (1961), a comedy movie directed by Paul May, 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
Rat Race (2001)
★ 6.3/10Also comedy
In an ensemble film about easy money, greed, manipulation and bad driving, a Las Vegas casino tycoon entertains his wealthiest high rollers -- a group that will bet on anything -- by pitting six ordinary people against…
2
Everything's Fifty Fifty (2024)
★ 6.5/10Also comedy
Marion and Andi thought they were happily divorced until their old love unexpectedly reignites during a family vacation with their son Milan.
3
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.
4
Help! (1965)
★ 6.9/10Also comedy
An obscure Eastern cult that practices human sacrifice pursues Ringo after he unknowingly puts on a ceremonial ring (that, of course, won't come off). On top of that, a pair of mad scientists, members of Scotland Yard…
5
Ocean's Eleven (1960)
★ 6.4/10Also comedy
Danny Ocean and his gang attempt to rob the five biggest casinos in Las Vegas in one night.
6
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.
7
Don't Tell Mom the Babysitter's Dead (1991)
★ 6.2/10Also comedy
Sue Ellen Crandell is a teenager eagerly awaiting her mother's summer-long absence. While the babysitter looks after her rambunctious younger siblings, Sue Ellen can party and have fun. But then the babysitter abruptly…
8
The Twelve Chairs (1970)
★ 6.2/10Also comedy
In 1920s Soviet Russia, a fallen aristocrat, a priest and a con artist search for a treasure of jewels hidden inside one of twelve dining chairs, lost during the revolution.
9
The Lizzie McGuire Movie (2003)
★ 6.3/10Also comedy
Lizzie McGuire has graduated from middle school and takes a trip to Rome, Italy with her class. And what was supposed to be only a normal trip, becomes a teenager's dream come true.
10
The Cocoanuts (1929)
★ 6.5/10Also comedy
During the Florida land boom, the Marx Brothers run a hotel, auction off some land and thwart a jewel robbery.
11
Beckenrand Sheriff (2021)
★ 6.7/10Also comedy
A lifeguard tries by all means to keep his home, an open-air swimming pool, from being closed.
12
Not My Day (2014)
★ 6.4/10Also comedy
When Banker Till (Axel Stein) is kidnapped during a bank robbery, he has the time of his life...
13
Men in the City 2 (2011)
★ 6.3/10Also comedy
The sequel of the "Men in the city" movie which reunites all the characters.
14
Sneakerella (2022)
★ 5.9/10Also comedy
When El, an aspiring sneaker designer from Queens, meets Kira King, the fiercely independent daughter of legendary basketball star and sneaker tycoon Darius King, sparks fly as the two bond over their mutual affinity…
15
Judy Moody and the Not Bummer Summer (2011)
★ 6/10Also comedy
Third-grader Judy Moody sets out to have the most thrilling summer of her life.
16
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…
17
A Very Brady Sequel (1996)
★ 5.9/10Also comedy
A man claiming to be Carol Brady's long-lost first husband, Roy Martin, shows up at the suburban Brady residence one evening. An impostor, the man is actually determined to steal the Bradys' familiar horse statue, a…
18
The Big Store (1941)
★ 6.3/10Also comedy
A detective is hired to protect the life of a singer, who has recently inherited a department store, from the store's crooked manager.
19
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.
20
High School Musical 2 (2007)
★ 6.5/10Also comedy
The East High Wildcats are gearing up for big fun as they land the coolest summer jobs imaginable. Troy, Gabriella, Chad, and Taylor have scored sweet gigs at the Lava Springs Country Club owned by Sharpay and Ryan's…