Movies Like Pillow to Post

If you liked Pillow to Post (1945), a comedy movie directed by Vincent Sherman, 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
A Song Is Born (1948)
★ 6.5/10Also comedy
The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want…
2
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…
3
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
4
Dennis the Menace (1993)
★ 5.9/10Also comedy
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
5
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.
6
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
7
The Sandlot 2 (2005)
★ 5.9/10Also comedy
A decade has passed in the small town where the original Sandlot gang banded together during the summer of ’62 to play baseball and battle the Beast. Now, back at the dugout, nine new kids descend on the diamond only…
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
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
10
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…
11
What Did You Do in the War, Daddy? (1966)
★ 5.9/10Also comedy
A by-the-book Captain is ordered to capture a strategic village in Italy. The Italian soldiers are willing to surrender, if they can have a festival first. The lieutenant convinces the Captain this is the only way…
12
Dave Chappelle: The Bird Revelation (2017)
★ 7.5/10Also comedy
Comedy juggernaut Dave Chappelle's fourth Netflix Special, taped on November 20th, 2017 at Los Angeles' Comedy Store.
13
Caveman (1981)
★ 6.7/10Also comedy
Disgraced and cast out of his tribe for lusting after Lana, the mate of the tribe's head muscle man, Atouk stumbles along gathering other misfits and learning a bit about the world outside of his cave. Eventually he…
14
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.
15
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.
16
LEGO Marvel Avengers: Mission Demolition (2024)
★ 6.5/10Also comedy
A young, aspiring hero and superhero fan inadvertently unleashes a powerful new villain looking to rid the world of the Avengers.
17
Johnny English Strikes Again (2018)
★ 6.3/10Also comedy
Disaster strikes when a criminal mastermind reveals the identities of all active undercover agents in Britain. The secret service can now rely on only one man - Johnny English. Currently teaching at a minor prep…
18
Amy Schumer: Mostly Sex Stuff (2012)
★ 5.9/10Also comedy
A ratings hit! Amy Schumer debuts her one-hour special in front of a live audience at the Historic Fillmore Theatre in San Francisco. Nothing is off limits as Schumer airs every hilarious, messed up detail of her…
19
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
20
Snoopy Presents: Welcome Home, Franklin (2024)
★ 7.7/10Also comedy
Franklin is new to town and hoping to make friends, but his usual tactics don't work on the Peanuts gang. When the Soap Box Derby arrives, he's sure it's a chance to impress new pals and teams up with the only other…