Movies like Who's the Caboose? (1997)
The best movies like Who's the Caboose? (1997) are Tall Girl (2019), Bronco Billy (1980) and You Will Meet a Tall Dark Stranger (2010). If Who's the Caboose? hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedAmerican Beauty (1999)8.0/10 from 13,548 votes
- NewestPlain and Dry (2025)Released 2025
Tall Girl (2019)
Jodi, the tallest girl in her high school, has always felt uncomfortable in her own skin. But after years of slouching, being made fun of, and avoiding attention at all costs, Jodi finally decides to find the confidence to stand tall.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisBronco Billy (1980)
An idealistic, modern-day cowboy struggles to keep his Wild West show afloat in the face of hard luck and waning interest.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisYou Will Meet a Tall Dark Stranger (2010)
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisIrreplaceable You (2018)
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisThe Other Sister (1999)
A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHitch (2005)
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMadame (2017)
Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid as a noblewoman to even out the number of guests. When the maid runs off with a wealthy guest, Anne must chase her around Paris to thwart the joyous and unexpected love affair.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisPicture Perfect (1997)
A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisAn Unexpected Christmas (2021)
Jamie hasn’t told his family that he and his now ex-girlfriend Emily broke up. After an inopportune run-in with Emily at the train station in his hometown, Jamie convinces her to pretend they’re still a couple to avoid ruining Christmas for his family.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLet's Make Love (1960)
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisGirl on a Bicycle (2013)
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisChristmas at the Drive-In (2022)
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDon't Think Twice (2016)
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWhat a Way to Go! (1964)
A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Is in the Air (2023)
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisChristmas with You (2022)
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisThey Won't Believe Me (1947)
On trial for murdering his girlfriend, philandering stockbroker Larry Ballentine takes the stand to claim his innocence and describe the actual, but improbable sounding, sequence of events that led to her death.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisD'Unbelievables D'Telly (1998)
Irish Comedy Starring Jon Kenny & Pat Shortt
Why it matches: Similar story and style · both comedy & drama
Heat (1972)
Former child star Joe Davis, reduced to living in a cheap Hollywood motel while struggling for acting jobs, is lusted after by nearly every woman he meets, including Jessica Todd, a tightly wound feminist who has recently come out as a lesbian. When Jessica's mother, Sally, an emotionally needy has-been actress, meets Joe, she moves him into her enormous, tacky mansion as her new boy toy and attempts to get him acting work.
Why it matches: Similar story and style · both comedy & drama
Plain and Dry (2025)
This unconventional rom-com follows Chadd, a deceiving womanizer, who is attempting to get laid on a first date. This satirical, laugh-out-loud date night, is something you will not want to miss!
Why it matches: Similar story and style · both comedy & romance
Intolerable Cruelty (2003)
A revenge-seeking gold digger marries a womanizing Beverly Hills lawyer with the intention of making a killing in the divorce.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisAmerican Beauty (1999)
Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after developing an infatuation with his daughter's attractive friend.
Why it matches: Similar story and style · both drama
Absolute CinemaMovies like thisCharlie's Angels (2000)
The captivating crime-fighting trio who are masters of disguise, espionage and martial arts are back! When a devious mastermind embroils them in a plot to destroy individual privacy, the Angels, aided by their loyal sidekick Bosley, set out to bring down the bad guys. But when a terrible secret is revealed, it makes the Angels targets for assassination.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisThe Discreet Charm of the Bourgeoisie (1972)
An upper-class sextet sits down to dinner but never eats, their attempts continually thwarted by a vaudevillian mixture of events both actual and imagined.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisThe Day of the Locust (1975)
Hollywood, 1930s. Tod Hackett, a young painter who tries to make his way as an art director in the lurid world of film industry, gets infatuated with his neighbor Faye Greener, an aspiring actress who prefers the life that Homer Simpson, a lone accountant, can offer her.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like thisBeneath the Valley of the Ultra-Vixens (1979)
Believe it or not, even Smalltown USA, those unfulfilled and unrelieved in the midst of plenty reside. Levonna and Lamar could have the perfect relationship, were it not for Lamar's obsession with rear entry.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisEat the Rich (1987)
Alex is a disgruntled waiter at a snobby exclusive restaurant who falls on hard times. Forced to deal with the contempt and disgust of the upper class, Alex & cohorts attempt to go on a rampage. Meanwhile, General Karprov and Spider plot to involve the inept anarchists into their plans to derail the prime-minister-to-be's campaign.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Who's the Caboose??
The closest matches to Who's the Caboose? are Tall Girl (2019), Bronco Billy (1980) and You Will Meet a Tall Dark Stranger (2010). Below are 27 more, each with the reason it matches.
What should I watch after Who's the Caboose??
Start with Tall Girl (2019), the closest match to Who's the Caboose?.
What is the highest-rated movie like Who's the Caboose??
American Beauty (1999), rated 8.0/10 by 13,548 TMDB users.
What is the newest movie like Who's the Caboose??
Plain and Dry (2025) is the most recent release on this list.
Are there English movies like Who's the Caboose??
Yes: Tall Girl (2019), Bronco Billy (1980) and You Will Meet a Tall Dark Stranger (2010).
How are movies similar to Who's the Caboose? chosen?
First come films that Trakt’s viewers watch alongside Who's the Caboose?, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.