Movies Like Damned If You Do

If you liked Damned If You Do (2000), a comedy movie directed by Jimmy Zeilinger, 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
Solid Serenade (1946)
★ 7.4/10Also comedy
Tom ties up Spike and sneaks into the courtyard of the glamorous Toodles Galore with his bass, hoping to woo her with his song, much to the annoyance of a sleeping Jerry.
2
The Bodyguard (1944)
★ 7.4/10Also comedy
Spike the bulldog, grateful to Jerry for getting him out of the dogcatcher's van, offers to help the little mouse any time he whistles. Tom, Jerry's feline tormentor, seeks to overcome this new disadvantage.
3
Casanova Cat (1951)
★ 6.7/10Also comedy
Tom heads for a big city penthouse to become acquainted with a rich pretty female cat that lives there. He brings her Jerry as a gift and does some humiliating things to Jerry. Jerry, in turn, attracts the attention of…
4
Sea Scouts (1939)
★ 6.4/10Also comedy
Donald is an admiral on a seagoing voyage with his nephews in which they encounter a ravenous shark.
5
Perfect Day (1929)
★ 7/10Also comedy
Two families embark on a pleasant Sunday picnic but manage to run into a variety of issues with their temperamental automobile. Each incident requires repeated exits and reboardings by Laurel, Hardy, their wives and…
6
Our Wife (1931)
★ 7.1/10Also comedy
Oliver is making plans to marry his sweetheart Dulcy with Stan as his best man, but the plans are thwarted when Dulcy's father sees a picture of Ollie and forbids the marriage. The couple plan to elope, and run away to…
7
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
8
His Mouse Friday (1951)
★ 6.5/10Also comedy
Tom is shipwrecked on an island, which is inhabited by at least one mouse - Jerry. To thwart the hungry cat, Jerry disguises himself as a cannibal.
9
A Knight for a Day (1946)
★ 6.6/10Also comedy
By accident, Cedric (Goofy), replaces his master, Sir Loinsteak, in the armor just before the joust with champion Sir Cumference.
10
Accident Man (2018)
★ 6.3/10Also comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
11
No Time for Nuts (2006)
★ 7.4/10Also comedy
Scrat comes across a time machine and is transported to various times all in pursuit of his beloved acorn.
12
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
13
Barbecue Brawl (1956)
★ 6.7/10Also comedy
Spike is showing his son Tyke how to barbecue when his cooking is disrupted by a typical Tom-and-Jerry chase.
14
Oliver the Eighth (1934)
★ 7.1/10Also comedy
Barbershop owners Stan and Ollie answer an ad in the newspaper from a wealthy widow looking for a husband. Ollie only mails in his response and is invited to the widow's mansion. Stan discovers his unmailed letter and…
15
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
16
The Big Bad Wolf (1934)
★ 6.5/10Also comedy
The Big Bad Wolf torments Little Red Riding Hood and the Three Little Pigs.
17
The Yankee Doodle Mouse (1943)
★ 7.2/10Also comedy
As Tom and Jerry stage their typical fight sequences, the patriotic soldier theme of the title is evidenced by such things as a carton of eggs labeled "Hen Grenades"; Jerry dropping light bulbs from an airplane like…
18
The Fixer Uppers (1935)
★ 6.8/10Also comedy
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
19
One Night at McCool's (2001)
★ 5.9/10Also comedy
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
20
Donald's Nephews (1938)
★ 6.5/10Also comedy
Donald's sister Dumbella sends her three sons Huey, Dewey, and Louie to visit their uncle Donald. They prove to be quite a handful for Donald, even with help from his book on child rearing.