Movies like The Great Gildersleeve (1942)
The best movies like The Great Gildersleeve (1942) are Fun with Dick and Jane (1977), Jerry Seinfeld: 23 Hours to Kill (2020) and Little Big League (1994). If The Great Gildersleeve hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedJohn Mulaney: Kid Gorgeous at Radio City (2018)7.9/10 from 259 votes
- Newest40 Dates and 40 Nights (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 thisJerry Seinfeld: 23 Hours to Kill (2020)
Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.
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 thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTrailer Park Boys: Don't Legalize It (2014)
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty deal. Meanwhile, Ricky’s dope growing business is under a major threat when the government announces a plan to legalize marijuana. Bubbles reluctantly joins them on his own quest to claim an inheritance left to him by his long-lost parents.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Kill the Messenger (2008)
An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAdam Sandler: Love You (2024)
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
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 thisEasy Money (1983)
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Oh My God (2013)
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: Humanity (2018)
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisEddie Murphy Raw (1987)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBill Burr: Why Do I Do This? (2008)
One of America's fastest-rising comedians, Bill Burr wields his razor-sharp wit with rare skill. In this brand-new stand-up performance, Bill takes aim at the stuff that drives us crazy, political correctness gone haywire, and girlfriends, or as he calls them: relentless psycho robots. A keenly observant social commentator, Bill Burr is also one of the funniest voices in comedy today.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRookie of the Year (1993)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisNikki Glaser: Someday You'll Die (2024)
Comedian and actress Nikki Glaser is back in her second HBO special, diving into a wide range of topics including why she doesn't want kids, the harsh realities of aging, her sexual fantasies and more.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGeorge Carlin: It's Bad for Ya! (2008)
It's Bad For Ya, Carlin's Emmy nominated 14th and final HBO special from March of 2008 features Carlin's noted irreverent and unapologetic observations on topics ranging from death, religion, bureaucracy, patriotism, overprotected children and big business to the pungent examinations of modern language and the decrepit state of the American culture.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies 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 thisStewie Griffin: The Untold Story (2005)
The maniacal baby of the Griffin family, Stewie, meets his future self. In doing this he discovers that his future image is not what he has anticipated because of a near death experience.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisMonkey Business (1952)
Research chemist Barnaby Fulton works on a fountain of youth pill for a chemical company. One of the labs chimps gets loose in the laboratory and mixes chemicals, but then pours the mix into the water cooler. When trying one of his own samples, washed down with water from the cooler, Fulton begins to act just like a twenty-year-old and believes his potion is working. Soon his wife and boss are also behaving like children.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBad Boy (1935)
An unemployed loafer who spends his time playing pool decides he's ready to look for a job so he can secure his girlfriend's parents' approval for their marriage.
Why it matches: Similar story and style · both comedy
South Park: Imaginationland (2008)
Some of the boys from South Park Elementary find themselves on a balloon ride to an imaginary land. Upon their arrival they're faced with an unimaginable threat.
Why it matches: Similar story and style · both comedy
Absolute CinemaMovies like thisTrading Places (1983)
A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisShe's All That (1999)
High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisDirty Rotten Scoundrels (1988)
Con artist Lawrence Jamieson is a longtime resident of a luxurious coastal resort, where he enjoys the lavish fruits of his deceptions -- that is, until a competitor, Freddy Benson, shows up. When the new guy's lowbrow tactics impinge on his own sophisticated work and believing him to be the infamous conman 'The Jackal', Lawrence resolves to get rid of him. Confident of his own duplicitous talents, he challenges Freddy to a winner-takes-all competition: whoever swindles their latest mark, American heiress Janet Colgate, out of $50,000 first can stay, while the other must leave town.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this40 Dates and 40 Nights (2026)
Ready to quit the dating scene altogether, burned-out Leah accepts her grandmother's outrageous challenge—40 dates in 40 nights in exchange for a year's rent—only to discover amidst the awkward dinners and unexpected sparks that her biggest obstacle to love is herself.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisMy Fair Lady (1964)
A snobbish phonetics professor agrees to a wager that he can take a flower girl and make her presentable in high society.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisLife Stinks (1991)
Affluent and arrogant businessman Goddard Bolt, feuding with rival Vance Crasswell over a land deal, makes a bet with Crasswell that he has the wits and street smarts to live penniless and anonymous on the rough streets of Los Angeles for thirty days. But Bolt has a rude awakening when the reality of homelessness hits him. Still, he finds a silver lining in a burgeoning romance with Molly, a former Broadway dancer who has fallen on hard times.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisI Should Have Killed That Bastard (2018)
The drama 'Descendants of Unicorn', which is in crisis due to a series of drop-offs by male actors. Staffs who cannot stop airing will start an emergency meeting.
Why it matches: Similar story and style · both comedy
The Great Race (1965)
Professional daredevil and white-suited hero, The Great Leslie, convinces turn-of-the-century auto makers that a race from New York to Paris (westward across America, the Bering Straight and Russia) will help to promote automobile sales. Leslie's arch-rival, the mustached and black-attired Professor Fate vows to beat Leslie to the finish line in a car of Fate's own invention.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like The Great Gildersleeve?
The closest matches to The Great Gildersleeve are Fun with Dick and Jane (1977), Jerry Seinfeld: 23 Hours to Kill (2020) and Little Big League (1994). Below are 27 more, each with the reason it matches.
What should I watch after The Great Gildersleeve?
Start with Fun with Dick and Jane (1977), the closest match to The Great Gildersleeve.
What is the highest-rated movie like The Great Gildersleeve?
John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.
What is the newest movie like The Great Gildersleeve?
40 Dates and 40 Nights (2026) is the most recent release on this list.
Are there English movies like The Great Gildersleeve?
Yes: Fun with Dick and Jane (1977), Jerry Seinfeld: 23 Hours to Kill (2020) and Little Big League (1994).
How are movies similar to The Great Gildersleeve chosen?
First come films that Trakt’s viewers watch alongside The Great Gildersleeve, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.