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Movies like Showgirls 2: Penny's from Heaven (2011)

The best movies like Showgirls 2: Penny's from Heaven (2011) are Milk Money (1994), Jolly Good Christmas (2022) and An Unexpected Christmas (2021). If Showgirls 2: Penny's from Heaven hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Milk Money (1994)

    Three young boys pool their money and pay V, a kindhearted prostitute, to strip for them. Afterward, she drives them home to the suburbs -- but then her car breaks down. It's just as well, though, because a mobster named Waltzer is after her, and V realizes the suburbs are the perfect place to hide. But things get a lot more complicated when V falls in love with Tom, a single father who is unaware of her real profession.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  2. Jolly Good Christmas (2022)

    David is an American architect who relocates across the pond to take up a job at a prestigious London firm. As the clock counts down to Christmas Day, David is running out of time to buy his girlfriend – who also happens to be his boss’s daughter – a thoughtful present so he resorts to buying her a somewhat uninspired gift card.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  3. An 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 this
  4. B&B Merry (2022)

    Tracey Wise is a renowned luxury travel blogger who is invited by Graham Cooper to a Christmas getaway in exchange for her review of his family’s small bed & breakfast, Silver Peak. Unfortunately, the humble B&B is facing tough competition from an upscale hotel resort nearby that has been stealing guests and threatening the survival of the family business.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  5. L.A. Without a Map (1999)

    An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

  6. Bronco 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 this
  7. The 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 this
  8. Limelight (1952)

    A fading music hall comedian tries to help a despondent ballet dancer learn to walk and to again feel confident about life.

    Why it matches: Recommended by TMDB viewers · both romance & drama

    Absolute CinemaMovies like this
  9. Step Up All In (2014)

    All-stars from previous installments convene in glittering Las Vegas, battling for a victory that could define their dreams and their careers.

    Why it matches: Recommended by TMDB viewers · both romance & drama

    Popcorn FlickMovies like this
  10. Let'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 this
  11. Fallen Angel (1945)

    An unemployed drifter, Eric Stanton wanders into a small California town and begins hanging around the local diner. While Eric falls for the lovely waitress Stella, he also begins romancing a quiet and well-to-do woman named June Mills. Since Stella isn't interested in Eric unless he has money, the lovelorn guy comes up with a scheme to win her over, and it involves June. Before long, murder works its way into this passionate love triangle.

    Why it matches: Recommended by TMDB viewers · both drama & romance

    Popcorn FlickMovies like this
  12. LaRoy, Texas (2024)

    Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.

    Why it matches: Recommended by TMDB viewers · both comedy & thriller

    Popcorn FlickMovies like this
  13. Flamingo Road (1949)

    A stranded carnival dancer takes on a corrupt political boss when she marries into small-town society.

    Why it matches: Recommended by TMDB viewers · both drama & romance

    Worth the HypeMovies like this
  14. My Brilliant Career (1979)

    A young woman who is determined to maintain her independence finds herself at odds with her family who wants her to tame her wild side and get married.

    Why it matches: Recommended by TMDB viewers · both drama & romance

    Popcorn FlickMovies like this
  15. Honey 3: Dare to Dance (2016)

    While attending college in Cape Town, Melea Martin feels constrained by the school's strict policies, and decides to set out on her own. Searching for a way to use her talents as a dancer and inspire the community around her, Melea rents a failing theater in order to put on a Hip-Hop Romeo and Juliet performance. But much like the Capulets and Montagues, conflicts between cast members threaten to bring the whole performance to a halt...

    Why it matches: Recommended by TMDB viewers · both drama & romance

    Popcorn FlickMovies like this
  16. They Live by Night (1949)

    An escaped convict, injured during a robbery, falls in love with the woman who nurses him back to health, but their relationship seems doomed from the beginning.

    Why it matches: Recommended by TMDB viewers · both romance & drama

    Popcorn FlickMovies like this
  17. The Naked City (1948)

    After a former model is drowned in her bathtub, Detective James Halloran and Lieutenant Dan Muldoon attempt to piece together her murder.

    Why it matches: Recommended by TMDB viewers · both drama & thriller

    Worth the HypeMovies like this
  18. The 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 this
  19. Catering Christmas (2022)

    A fledgling caterer, Molly Frost, is hired by Jean Harrison, the perfectionistic director of the renowned Harrison Foundation, to cater this year’s annual Christmas Gala dinner. Things get complicated when Molly falls for Jean’s nephew, Carson, 30s, a travel photographer with no desire to take over the family’s foundation… until his aunt assigns him to the task of making sure the catered dinner goes perfectly.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  20. Christmas on Windmill Way (2023)

    Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas bread. But Mia's world is rocked when she learns that Ann was having financial troubles and had to sell the land deed to the Windmill Way property in her family for generations. Making matters worse, the buyer is Mia's former boyfriend, property developer Brady Schaltz, who must let Mia and Ann know the Meijer family-owned heritage Dutch sawmill, renowned for the past 90 years for its fine millwork and beautiful wooden furniture, will be torn down to put up a luxurious resort.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

  21. Ravenous (1999)

    After arriving at his new, remote Army outpost, Capt. John Boyd and his regiment aid a wounded frontiersman who recounts a horrifying tale of a wagon train murdered by its supposed guide – a vicious U.S. Army colonel gone rogue. Fearing the worst, the regiment heads out into the wilderness to verify the gruesome claims.

    Why it matches: Similar story and style · both comedy & drama

    Popcorn FlickMovies like this
  22. The Sisterhood of the Traveling Pants 2 (2008)

    Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and the summer beyond, but remain in touch by sharing their experiences with each other.

    Why it matches: Similar story and style · both comedy & drama

    Popcorn FlickMovies like this
  23. The Prince of Tides (1991)

    A troubled Southern man talks to his suicidal sister's psychiatrist about their family history and falls in love with her (and New York City) in the process.

    Why it matches: Similar story and style · both drama & romance

    Popcorn FlickMovies like this
  24. Dandelion (2025)

    In 1970s Los Angeles, rebellious queer teen Margaret gets thrown out of yet another foster placement and finds herself in the company of a mysterious social worker who's tasked with finding her a new home before the break of dawn. At odds and forced to travel the city together, Margaret realizes that running may not be her only option.

    Why it matches: Similar story and style · both comedy & drama

  25. Sealed With a Kiss: Wedding March 6 (2021)

    The modest wedding plans of a celebrity and his down-to-earth fiancée escalate while Mick gets an enticing opportunity Olivia won’t let him refuse, putting their own big day in jeopardy.

    Why it matches: Similar story and style · both comedy & romance

  26. D3: The Mighty Ducks (1996)

    The Ducks are offered scholarships at Eden Hall Academy but struggle with their new coach's methods and come under pressure from the board to retain their scholarships before their big game against the Varsity team.

    Why it matches: Similar story and style · both comedy & drama

    Popcorn FlickMovies like this
  27. Never Mind the Wall (2001)

    Germany 1982: The country is divided into two parts. Nele, coming from West-Germany, travels to East-Germany where she meets Captain, singer of a band. They fall in love with each other, but the regime "takes care" of their relationship, meaning: They can not see each other again. Germany 1990: The country is reunited. Nele starts searching their lost love...

    Why it matches: Similar story and style · both drama & romance

  28. Buffy the Vampire Slayer (1992)

    Blonde, bouncy Buffy is your typical high school cheerleader. But all that changes when a strange man informs her she's been chosen by fate to kill vampires.

    Why it matches: Similar story and style · both comedy

  29. From Dusk Till Dawn 3: The Hangman's Daughter (2000)

    Set one hundred years ago, outlaw Johnny Madrid, after narrowly escaping death, goes on the run with the hangman's sensuous daughter Esmeralda by his side.

    Why it matches: Similar story and style · both thriller

  30. Son of the Mask (2005)

    Tim Avery, an aspiring cartoonist, finds himself in a predicament when his dog stumbles upon the mask of Loki. Then after conceiving an infant son "born of the mask", he discovers just how looney child raising can be.

    Why it matches: Similar story and style · both comedy

Like Showgirls 2: Penny's from Heaven and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Showgirls 2: Penny's from Heaven?

The closest matches to Showgirls 2: Penny's from Heaven are Milk Money (1994), Jolly Good Christmas (2022) and An Unexpected Christmas (2021). Below are 27 more, each with the reason it matches.

What should I watch after Showgirls 2: Penny's from Heaven?

Start with Milk Money (1994), the closest match to Showgirls 2: Penny's from Heaven.

What is the highest-rated movie like Showgirls 2: Penny's from Heaven?

Limelight (1952), rated 7.9/10 by 627 TMDB users.

What is the newest movie like Showgirls 2: Penny's from Heaven?

Dandelion (2025) is the most recent release on this list.

Are there English movies like Showgirls 2: Penny's from Heaven?

Yes: Milk Money (1994), Jolly Good Christmas (2022) and An Unexpected Christmas (2021).

How are movies similar to Showgirls 2: Penny's from Heaven chosen?

First come films that Trakt’s viewers watch alongside Showgirls 2: Penny's from Heaven, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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