Movies Like The Pickaninny

If you liked The Pickaninny (1921), a comedy movie directed by Robert P. Kerr and James Parrott, 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 Tramp (1915)
★ 6.5/10Also comedy
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
2
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…
3
My Wife's Relations (1922)
★ 6.2/10Also comedy
Buster and a woman are mistakenly married and her initially unfriendly family begins to treat him nicely when they come to believe he has a large inheritance awaiting him.
4
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…
5
The Railrodder (1965)
★ 6.8/10Also comedy
After literally swimming across the Atlantic Ocean, an Englishman takes a country trip across Canada on a railcar.
6
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.
7
The Bank (1915)
★ 6.3/10Also comedy
A janitor at a bank is in love with a secretary and dreams that she has fallen in love with him too.
8
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
9
Solid Serenade (1946)
★ 7.5/10Also 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.
10
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
11
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.
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
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.
14
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
15
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.
16
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…
17
Dough and Dynamite (1914)
★ 6.1/10Also comedy
Pierre and Jacques are working as waiters at a restaurant where the cooks go on strike. When the two are forced to work as bakers, the striking cooks put dynamite in the dough, with explosive results.
18
Eddie Murphy Raw (1987)
★ 7.2/10Also comedy
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
19
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
20
Sufferin' Cats! (1943)
★ 7.1/10Also comedy
Tom fights with another cat over Jerry.