Movies Like 55 & Older

If you liked 55 & Older (2013), a comedy movie directed by Kevin Armstrong, 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
American Dreamer (2022)
★ 6/10Also comedy
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.
2
Good Neighbor Sam (1964)
★ 6.6/10Also comedy
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
3
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.
4
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
5
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.
6
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
7
The Bed Sitting Room (1969)
★ 5.9/10Also comedy
In the hazy aftermath of World War III, the fallout from a 'nuclear misunderstanding' is producing strange mutations amongst the survivors, and the noble Lord Fortnum finds himself transforming into a bed sitting room.
8
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
9
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
10
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
11
Zapped (2014)
★ 6.1/10Also comedy
Zoey is a talented dancer whose organized life is rudely disrupted when she moves in with her new step-dad and three step-brothers, until she discovers a dog-training app that can get boys to obey her every command…
12
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…
13
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.
14
The Trouble with Angels (1966)
★ 6.7/10Also comedy
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
15
Black Sheep (1996)
★ 6.1/10Also comedy
When dignified Albert Donnelly runs for Governor, his team moves to keep his slow-witted and klutzy younger brother, Mike, out of the eye of the media. To baby-sit Mike, the campaign assigns sarcastic Steve, who gets…
16
Malibu Rescue: The Next Wave (2020)
★ 6.2/10Also comedy
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on…
17
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
18
The Associate (1996)
★ 6.2/10Also comedy
Laurel Ayres is a businesswoman trying to make it but unfortunately she works at a investment firm where she does all the work but all the senior investors like Frank Peterson grab all the credit. She then leaves and…
19
Godspell (1973)
★ 6.7/10Also comedy
In modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
20
The Errand Boy (1961)
★ 6.2/10Also comedy
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty…