Movies like To Bet One's Boot
The best movies like To Bet One's Boot are Fun with Dick and Jane (1977), Me Time (2022) and The Ladies Man (1961). If To Bet One's Boot hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Philadelphia Story (1940)7.5/10 from 1,045 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Fun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMe Time (2022)
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Ladies Man (1961)
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 all these females?
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 thisHard to Die (1990)
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 of killings six months previously, is at the bottom of the whole thing. Little do they know the real horror that they face in the end.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBabes (2024)
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBrain Donors (1992)
Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit the rich widow and her scheming big-shot lawyer, who also wants to run the ballet.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Selective Outrage (2023)
Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Armageddon (2023)
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Roast of Tom Brady (2024)
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAdventures in Public School (2018)
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDuplex (2003)
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBill Burr: Drop Dead Years (2025)
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 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 thisPlaydate (2025)
When out-of-work accountant Brian joins stay-at-home dad Jeff for a playdate with their sons, he expects a laid-back afternoon. Instead, they're chased by mercenaries, and Brian—totally unprepared—must survive one absurd obstacle after another.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Ridiculous (2026)
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRobot Chicken: Star Wars (2007)
A series of 30 sketches, following the hilarious antics of various characters from a galaxy, far, far away.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisPatrice O'Neal: Elephant in the Room (2011)
Filmed at the New York Comedy Festival, comedian Patrice O'Neal stars in his first and only full-length stand-up special. Featuring 40 minutes of additional content not seen on television, Patrice brings his trademark absurdism and friendly yet no-holds-barred style to material on race and gender politics, relationships and more.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJimmy Carr: Natural Born Killer (2024)
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Philadelphia Story (1940)
When a rich woman's ex-husband and a tabloid-type reporter turn up just before her planned remarriage, she begins to learn the truth about herself.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this50 First Dates (2004)
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisNightmare at Camp Bloodbath (2022)
After discovering their lodge totaled by a neighboring camp, two counselors are stalked and prayed upon by the local legend Terrance Fisher in his slapstick parody.
Why it matches: Similar story and style · both comedy
Three Women and a Possible Fire Next Door (2025)
Two roommates (and their friend) must decide whether or not to evacuate their apartment.
Why it matches: Similar story and style · both comedy
The Gazebo (1959)
TV writer Elliott Nash buries a blackmailer under the new gazebo in his suburban backyard. But the nervous man can't let the body rest there.
Why it matches: Similar story and style · both comedy
Barnyard (2006)
Otis is a mischievous, carefree Holstein cow who lives on a farm where, unbeknownst to humans, the animals are anthropomorphic. He prefers having fun with his best friends: Pip the mouse, Freddy the ferret, Peck the rooster, and Pig the pig - rather than following strict rules and accepting responsibility. But when his adoptive father is killed in a coyote attack, he has a heavy responsibility thrust upon him to become leader of his farm home's community.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisA Choice of Coward: Blithe Spirit (1964)
While holding a séance for skeptical novelist Charles Condomine, self-proclaimed 'spiritualist medium' Madame Arcati inadvertently summons the spirit of his deceased first wife Elvira, leading to an increasingly complex love triangle with Ruth, his current wife of five years.
Why it matches: Similar story and style · both comedy
Bell, Book and Candle (1958)
Gillian Holroyd, a modern-day witch, becomes smitten with her handsome upstairs neighbor, Shep Henderson. Using her magical powers, she casts a love spell on him, only to face unexpected complications when genuine feelings emerge, threatening her supernatural abilities.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Dukes of Hazzard (2005)
Cousins, Bo and Luke Duke, with the help of their eye-catching cousin, Daisy and moonshine-running Uncle Jesse, try and save the family farm from being destroyed by Hazzard County's corrupt commissioner, Boss Hogg. Their efforts constantly find the 'Duke Boys' eluding authorities in 'The General Lee', their 1969 orange Dodge Charger that keeps them one step ahead of the dimwitted antics of the small southern town's Sheriff, Roscoe P. Coltrane.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisAnchorman: The Legend of Ron Burgundy (2004)
It's the 1970s and San Diego anchorman Ron Burgundy is the top dog in local TV, but that's all about to change when ambitious reporter Veronica Corningstone arrives as a new employee at his station.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like To Bet One's Boot?
The closest matches to To Bet One's Boot are Fun with Dick and Jane (1977), Me Time (2022) and The Ladies Man (1961). Below are 27 more, each with the reason it matches.
What should I watch after To Bet One's Boot?
Start with Fun with Dick and Jane (1977), the closest match to To Bet One's Boot.
What is the highest-rated movie like To Bet One's Boot?
The Philadelphia Story (1940), rated 7.5/10 by 1,045 TMDB users.
What is the newest movie like To Bet One's Boot?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like To Bet One's Boot?
Yes: Fun with Dick and Jane (1977), Me Time (2022) and The Ladies Man (1961).
How are movies similar to To Bet One's Boot chosen?
First come films that Trakt’s viewers watch alongside To Bet One's Boot, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.