Movies like When the Clouds Roll By (1919)
The best movies like When the Clouds Roll By (1919) are Love, Weddings & Other Disasters (2020), Christmas with You (2022) and What's Love Got to Do with It? (2023). If When the Clouds Roll By hooked you with its romance and action, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Purple Rose of Cairo (1985)7.4/10 from 1,197 votes
- NewestChampagne Problems (2025)Released 2025
Love, Weddings & Other Disasters (2020)
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
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 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 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 thisThe Bachelor and the Bobby-Soxer (1947)
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to date Susan until the crush abates.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies 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 thisKiss Me, Stupid (1964)
While traveling home from Vegas, an amorous lounge singer named Dino gets conned by a local mechanic/songwriter into staying in town for the night. The mechanic's songwriting partner, Orville, offers Dino his home for overnight lodging and enlists a local waitress/call girl to pose as his wife in order to placate Dino's urges.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisThe Secret Life of Walter Mitty (1947)
Walter Mitty, a daydreaming writer with an overprotective mother, likes to imagine that he is a hero who experiences fantastic adventures. His dream becomes reality when he accidentally meets a mysterious woman who hands him a little black book. According to her, it contains the locations of the Dutch crown jewels hidden since World War II. Soon, Mitty finds himself in the middle of a confusing conspiracy, where he has difficulty differentiating between fact and fiction.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThis Little Love of Mine (2021)
Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s grandfather – asks Laura to travel to the island and deliver a contract to make Chip his heir, she leaves behind her practice and fiancé Owen to convince her childhood friend to sign a contract that will make him a billionaire.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisDouble Threat (2022)
With ruthless mobsters on her tail, a young woman with a split personality becomes entangled with a man on a pilgrimage across the country to scatter his brother's ashes.
Why it matches: Recommended by TMDB viewers · both action & comedy
Popcorn FlickMovies like thisGood Advice (2001)
An investment banker loses everything and must discover what's really important in life.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisThe Purple Rose of Cairo (1985)
Cecilia is a waitress in New Jersey, living a dreary life during the Great Depression. Her only escape from her mundane reality is the movie theatre. After losing her job, Cecilia goes to see 'The Purple Rose of Cairo' in hopes of raising her spirits, where she watches dashing archaeologist Tom Baxter time and again.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies 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 thisChampagne Problems (2025)
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisFalling for Christmas (2022)
An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisI Love You Again (1940)
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisThe Other End of the Line (2007)
An employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisEasy Virtue (2008)
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
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 this
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Frequently asked questions
What are the best movies like When the Clouds Roll By?
The closest matches to When the Clouds Roll By are Love, Weddings & Other Disasters (2020), Christmas with You (2022) and What's Love Got to Do with It? (2023). Below are 17 more, each with the reason it matches.
What should I watch after When the Clouds Roll By?
Start with Love, Weddings & Other Disasters (2020), the closest match to When the Clouds Roll By.
What is the highest-rated movie like When the Clouds Roll By?
The Purple Rose of Cairo (1985), rated 7.4/10 by 1,197 TMDB users.
What is the newest movie like When the Clouds Roll By?
Champagne Problems (2025) is the most recent release on this list.
Are there English movies like When the Clouds Roll By?
Yes: Love, Weddings & Other Disasters (2020), Christmas with You (2022) and What's Love Got to Do with It? (2023).
How are movies similar to When the Clouds Roll By chosen?
First come films that Trakt’s viewers watch alongside When the Clouds Roll By, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.