Movies like Penny Princess (1952)
The best movies like Penny Princess (1952) are Good Advice (2001), Easy Virtue (2008) and Girl on a Bicycle (2013). If Penny Princess 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 ratedThe Diamond Arm (1969)7.7/10 from 363 votes
- NewestChampagne Problems (2025)Released 2025
Good 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 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 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 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 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 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 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 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 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 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 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 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 thisA Hollywood Christmas (2022)
Jessica, a young, up-and-coming filmmaker in Hollywood has made a name for herself directing Christmas movies. But when handsome network executive Christopher shows up threatening to halt production on her latest movie, Jessica’s assistant, Reena, points out the irony: Jessica isn’t just trying to save her Christmas movie, she’s actually living in one. Jessica must now juggle all the classic tropes—her actors falling in and out of love, a wayward elf dog, and her own stirring romantic feelings for her perceived nemesis—in order to get her movie and her life to their happy endings.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMr. Lucky (1943)
A conman poses as a war relief fundraiser, but when he falls for a charity worker, his conscience begins to trouble him.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies 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 thisWhisky Galore (2016)
The story of the inhabitants of the isolated Scottish island of Todday, in the Outer Hebrides, where gloom sets in as their wartime rationing of whisky runs out. When cargo ship the SS Cabinet Minister runs aground the shrewd islanders run rings around the buffoonish English Home Guard commander Captain Waggett and conspire to hide away cases of the precious amber nectar.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisThe Thrill of It All (1963)
A housewife's sudden rise to fame as a soap spokesperson leads to chaos in her home life.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisSilk Stockings (1957)
After three bumbling Soviet agents fail in their mission to retrieve a straying Soviet composer from Paris, the beautiful, ultra-serious Ninotchka is sent to complete their mission and to retrieve them. She starts out condemning the decadent West, but gradually falls under its spell—with the help of an American movie producer. A remake of Ninotchka (1939).
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies 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 thisFrench Kiss (1995)
After her fiancee admits to infidelity while on a business trip in France, a woman attempts to get her lover back and marry him by traveling to Paris despite her crippling fear of flying. On the way she unwittingly smuggles something of value that has a charming crook chasing her across France as she chases after her future husband.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisTopkapi (1964)
Arthur Simon Simpson is a small-time crook biding his time in Greece. One of his potential victims turns out to be a gentleman thief planning to steal the emerald-encrusted dagger of the Mehmed II from Istanbul's Topkapi Museum.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisDon't Think About It (2008)
Still an unsuccessful punk rock musician at 36, Stefano returns to his hometown in the countryside to help with his family's business.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisSmokey and the Bandit (1977)
A race car driver tries to transport an illegal beer shipment from Texas to Atlanta in under 28 hours, picking up a reluctant bride-to-be on the way.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisHot Pursuit (1987)
High school student Dan Bartlett misses the plane he was supposed to be on with his rich girlfriend and her family on the way to a Caribbean vacation during a school break. He flies there alone, and runs into a series of characters and misadventures as he tries to catch up.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisExit to Eden (1994)
Photographer Elliot Slater has inadvertently snapped the only existing photos of elusive jewel thief Omar. When Elliot leaves for a private vacation on an S&M island, he is followed by Omar, Omar's partner, Nina, and undercover police officers Fred and Sheila. Unaware of the number of people chasing him, Elliot enjoys his stay at the resort, and finds himself falling in love with head dominatrix Lisa.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisThe Diamond Arm (1969)
A diamond smuggling operation goes wrong when an ordinary Soviet citizen becomes unwittingly involved, and the criminals are forced to court him to retrieve their diamonds.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisFun with Dick and Jane (2005)
After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty good at robbing people and even enjoy it – but they have second thoughts when they're reminded that crime can hurt innocent people. When the couple hears that Globodyne boss Jack McCallister actually swindled the company, they plot revenge.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisLa pietra del paragone (2007)
LA PIETRA DEL PARAGONE (The Touchstone) concerns the Count Asdrubale who is wealthy and therefore of great interest to many women – notably Aspasia, Fulvia, and Clarice. Only Clarice, however, loves him for something other than his riches. There are also male hangers-on: the corrupt journalist Macrobio, the poetaster Pacuvio, and Giocondo, who is Asdrubale's true friend, but who has his own eyes on Clarice. To test his friends and would-be fiancées, Asdrubale pretends that he has been bankrupted. Sure enough, only Clarice and Giocondo stand by him, and when his fortune is "miraculously" saved, the three have the last laugh on everyone else... or do they? This production is set in what looks like the early 1960s. But the real innovation is the use of blue screen technology: using tiny cameras and sets, along gigantic screens hanging over the stage, a kind of video mixing makes the singers appear to inhabit any number of fanciful settings and perform a myriad of improbable actions.
Why it matches: Similar story and style · both comedy
Paandi Naattu Thangam (1989)
Thangapandian, an honest forest officer, is transferred to a village. The village chief cuts illegally the sandalwood trees. Radha is brought up by her adoptive family. When she was young, her father, a famous singer, died in a car accident. Thangapandian falls in love with Radha. What transpires later forms the crux of the story.
Why it matches: Similar story and style · both romance
Like Penny Princess and something else?
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Frequently asked questions
What are the best movies like Penny Princess?
The closest matches to Penny Princess are Good Advice (2001), Easy Virtue (2008) and Girl on a Bicycle (2013). Below are 27 more, each with the reason it matches.
What should I watch after Penny Princess?
Start with Good Advice (2001), the closest match to Penny Princess.
What is the highest-rated movie like Penny Princess?
The Diamond Arm (1969), rated 7.7/10 by 363 TMDB users.
What is the newest movie like Penny Princess?
Champagne Problems (2025) is the most recent release on this list.
Are there English movies like Penny Princess?
Yes: Good Advice (2001), Easy Virtue (2008) and Girl on a Bicycle (2013).
How are movies similar to Penny Princess chosen?
First come films that Trakt’s viewers watch alongside Penny Princess, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.