Movies like Wholesailing Along (1936)
The best movies like Wholesailing Along (1936) are American Dreamer (2022), Eddie Murphy Raw (1987) and The Distinguished Gentleman (1992). If Wholesailing Along hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Wholesailing Along
Quick picks
- Highest ratedEddie Murphy Raw (1987)7.2/10 from 394 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
American Dreamer (2022)
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 thisThe Distinguished Gentleman (1992)
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows from lobbyists.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMr. Bones (2001)
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
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 thisGabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
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 this29th Street (1991)
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
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 thisFun 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 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 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 this2 Minutes of Fame (2020)
An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA-Haunting We Will Go (1942)
Stan and Ollie get involved with con men, crooks, a genial magician, and two interchangeable coffins with disastrous but funny results.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisJimmy O. Yang: Good Deal (2020)
In his debut standup special, Good Deal, Jimmy will tell you all about his take on Asian representation, how he learned to speak English from rap videos, dating tall women, and pursuing his dreams only to disappoint his old school Chinese parents. From assimilation to representation, Jimmy O. Yang delivers an absolutely hilarious hour of comedy in Good Deal.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHeld Up (1999)
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisSarah Silverman: We Are Miracles (2013)
In her first-ever HBO solo special, Sarah Silverman takes the stage for an evening of adults-only stand-up comedy. Taped live in front of an intimate audience of 39 fans at Largo, a music and comedy club in Los Angeles, Sarah Silverman: We Are Miracles features Silverman taking aim at such subjects as cell-phone porn, crazy religions, specialty deodorants, terrible roommates, eyebrow waxing, her 19-year-old dog, Obama and Republicans, having babies, Pixar movies, the miracle of existence, and more.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDylan Moran: Like, Totally (2006)
Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 this
Like Wholesailing Along and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Wholesailing Along?
The closest matches to Wholesailing Along are American Dreamer (2022), Eddie Murphy Raw (1987) and The Distinguished Gentleman (1992). Below are 17 more, each with the reason it matches.
What should I watch after Wholesailing Along?
Start with American Dreamer (2022), the closest match to Wholesailing Along.
What is the highest-rated movie like Wholesailing Along?
Eddie Murphy Raw (1987), rated 7.2/10 by 394 TMDB users.
What is the newest movie like Wholesailing Along?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Wholesailing Along?
Yes: American Dreamer (2022), Eddie Murphy Raw (1987) and The Distinguished Gentleman (1992).
How are movies similar to Wholesailing Along chosen?
First come films that Trakt’s viewers watch alongside Wholesailing Along, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.