Movies like How Bill Squared It with His Boss (1914)
The best movies like How Bill Squared It with His Boss (1914) are Taking Care of Business (1990), The Errand Boy (1961) and I Love My Dad (2022). If How Bill Squared It with His Boss hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
How Bill Squared It with His Boss
Quick picks
- Highest ratedThunderstruck (2012)6.2/10 from 261 votes
- NewestDriver's Ed (2026)Released 2026
Taking Care of Business (1990)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Errand Boy (1961)
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 ever finds is that he can cause havoc no matter what he does.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisI Love My Dad (2022)
A hopelessly estranged father catfishes his son in an attempt to reconnect.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisWhy Worry? (1923)
A hypochondriac vacations in the tropics for the fresh air - and finds himself in the middle of a revolution instead.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShanghaied (1915)
A shipowner intends to scuttle his ship on its last voyage to get the insurance money. Charlie, a tramp in love with the owner's daughter, is grabbed by the captain and promises to help him shanghai some seamen. The daughter stows away to follow Charlie. Charlie assists in the galley and attempts to serve food during a gale.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMy Wife's Relations (1922)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGood Neighbor Sam (1964)
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 appearance.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Wedding Year (2019)
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisPolice (1916)
Charlie is released from prison and immediately swindled by a fake parson. A fellow ex-convict convinces Charlie to help burglarize a house.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisNo Time for Sergeants (1958)
Georgia farm boy Will Stockdale is about to bust with pride. He’s been drafted. Will’s ready. But is Uncle Sam ready for Will?
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDriver's Ed (2026)
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Woman (1915)
Mother, father and daughter go to the park. The women doze off on a bench while the father plays a hide-and-seek game with a girl, blindfolded. Charlie leads him into a lake. Both dozing ladies on the bench fall for Charlie and invite him for dinner. The father returns home with a friend. Charlie rushes upstairs and dresses like a woman, shaving his mustache. Both men fall for Charlie.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLittle Big League (1994)
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 orders from a 12-year-old.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSchizopolis (1997)
A man works for the unpleasant guru of a Scientology-like movement.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLiberty (1929)
While changing clothes in a getaway car, escaped convicts Stan and Ollie mistakenly put on each other's pants. They spend the rest of the film trying to exchange pants in various unlikely settings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThicker Than Water (1935)
Oliver's in trouble with his wife after missing a payment on their furniture, having given the money to Stanley, who used it instead to pay Mrs. Hardy for his room and board. At Stan's suggestion Ollie then withdraws the couple's savings from the bank to pay for the furniture and inadvertently pays virtually the whole amount at an auction for a grandfather clock which is soon crushed under a passing truck. Mrs Hardy then unintentionally causes serious injuries to Ollie requiring him to be rushed to hospital for a blood transfusion. The doctor conscripts Stan to be the unwilling blood donor. Problems occur with the transfusion and when Stan and Ollie leave the hospital they appear to have morphed into each other.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisMe and My Pal (1933)
On the morning of his wedding to oil baron Peter Cucumber's daughter, Ollie receives a jigsaw puzzle from Stan as a wedding gift. The boys soon become absorbed in the puzzle. A taxi driver, butler, policeman and messenger boy join in as well.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSextuplets (2019)
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHis Secretary (1925)
When a secretary overhears her boss disparaging her looks, she decides to show him how wrong he is.
Why it matches: Similar story and style · both comedy
Nobody's Kid (1921)
Because of the circumstances of her parents' marriage her grandfather rejects their child, Mary. Following her their deaths she is placed in an orphanage where Mary finds hardship.
Why it matches: Similar story and style · both comedy
Jolts and Jewelry (1917)
Pa Glitters and his daughter are beset upon by Slippery Ike who is intent on separating them from their jewels until Bunco Charley comes to their rescue in fine comic fashion.
Why it matches: Similar story and style · both comedy
Turks and Troubles (1917)
Hafed, a Turkish prince, imprisons an American girl and her father. The girl sends for Jim, who attempts a rescue. Jim is captured, but Hafed's jealous wife helps them escape. When the initial escape fails, Jim returns in disguise as a dancing girl. He dances for Hafed, luring him into a private encounter where Jim's identity is revealed. A fight leads Jim to take refuge in a tree. Surrounded by guards, Jim summons a warship. A shell from the warship blows up the tree, landing Jim safely on the battleship's deck and securing his escape.
Why it matches: Similar story and style · both comedy
Footlights and Fakers (1917)
Short comedy set against the backstage lives of a group of performers.
Why it matches: Similar story and style · both comedy
He Never Touched Me (1917)
Slapstick comedy short about a quarreling couple and a nosy mother-in-law.
Why it matches: Similar story and style · both comedy
Somewhere in Any Place (1917)
One of many Larry Semon directed Vitagraph comic shorts. Like a large portion of them this is lost.
Why it matches: Similar story and style · both comedy
Big Bluffs and Bowling Balls (1917)
Two blowhard amateur bowlers boast about their prowess only to be shown up for the Big Bluffs they are.
Why it matches: Similar story and style · both comedy
The Son of Wallingford (1921)
A young man's journey into adulthood, love, and ambition, inspired by a serial by George Randolph Chester exploring themes of love, ambition, and self-discovery, set against the backdrop of the Roaring Twenties.
Why it matches: Similar story and style · both comedy
Are You a Mason? (1915)
Frank Perry's wife Helen is away visiting her mother, and he uses this "free time" for a night of drinking at a nightclub. Unfortunately, when he tries to return home, he enters the wrong house and is nearly arrested When Helen comes back he tells her that the "incident" was actually an initiation rite of the Masons, knowing that his wife has always wanted him to join the group. She excitedly tells her father about Frank's becoming a Mason, since her father is also a Mason. What neither she nor Frank know is that her father has actually been doing the same thing Frank is--pretending to be a Mason when he actually isn't. Complications ensue.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like How Bill Squared It with His Boss?
The closest matches to How Bill Squared It with His Boss are Taking Care of Business (1990), The Errand Boy (1961) and I Love My Dad (2022). Below are 27 more, each with the reason it matches.
What should I watch after How Bill Squared It with His Boss?
Start with Taking Care of Business (1990), the closest match to How Bill Squared It with His Boss.
What is the highest-rated movie like How Bill Squared It with His Boss?
Thunderstruck (2012), rated 6.2/10 by 261 TMDB users.
What is the newest movie like How Bill Squared It with His Boss?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like How Bill Squared It with His Boss?
Yes: Taking Care of Business (1990), The Errand Boy (1961) and I Love My Dad (2022).
How are movies similar to How Bill Squared It with His Boss chosen?
First come films that Trakt’s viewers watch alongside How Bill Squared It with His Boss, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.