Movies Like Sunless Sunday

If you liked Sunless Sunday (1921), a comedy movie directed by Charles Reisner, 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
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.
2
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.
3
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.
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
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.
6
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
7
The Geisha Boy (1958)
★ 6.4/10Also comedy
Gilbert Wooley is a second-rate magician who is sent to entertain the troops in the pacific. During his time in Japan he becomes attached to a little orphan boy.
8
The Hoose-Gow (1929)
★ 6.8/10Also comedy
Stan and Ollie arrive as new inmates at a prison after apparently taking part in a hold-up raid, a raid they tell a prison officer they were only watching. The usual mayhem ensues.
9
The Willoughbys (2020)
★ 7.1/10Also comedy
When the four Willoughby children are abandoned by their selfish parents, they must learn how to adapt their Old-Fashioned values to the contemporary world in order to create something new: The Modern Family.
10
Airborne (1993)
★ 6.1/10Also comedy
Good-natured teen surfer Mitchell Goosen finds himself staying with his aunt and uncle in Cincinnati, Ohio when his parents head to Australia for work. There he meets his cousin, Wiley, and together they try to…
11
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.
12
Love Happy (1949)
★ 5.8/10Also comedy
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
13
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.
14
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…
15
Mr. Bones (2001)
★ 6/10Also comedy
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.
16
Arctic Dogs (2019)
★ 5.9/10Also comedy
Animals band together to save the day when the evil Otto Von Walrus hatches a sinister scheme to accelerate global warming and melt the Arctic Circle.
17
Take the Money and Run (1969)
★ 7.1/10Also comedy
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
18
Welcome to Collinwood (2002)
★ 6.1/10Also comedy
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
19
A Night in Casablanca (1946)
★ 6.8/10Also comedy
The Marx Brothers are employed at a hotel in postwar Casablanca, where a ring of Nazis is trying to recover a cache of stolen treasure.
20
Recess: All Growed Down (2003)
★ 6.5/10Also comedy
T.J. and The Recess Gang are kidnapped by the Third Street School's kindergartners, who are in turn being bullied by a new kid in their class.