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Movies like Princess Sissy (1939)

The best movies like Princess Sissy (1939) are Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), A Burlesque on Carmen (1915) and Military Academy (2007). If Princess Sissy hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Gabriel 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 this
  2. A Burlesque on Carmen (1915)

    A gypsy seductress is sent to sway a goofy officer to allow a smuggling run.

    Why it matches: Recommended by TMDB viewers · both comedy

  3. Military Academy (2007)

    The movie deals with a guy who gets to join the German Bundeswehr involuntarily because a colleague loses his denial papers in order to get the chance to get down on his girlfriend. When entering the Bundeswehr he acts like a giant idiot and of course gets in one room with some of the biggest losers around. The loser turns out to be a hero and leads his loser-colleagues to win a contest with the local US army squad.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. Dennis the Menace (1993)

    Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam comes to town.

    Why it matches: Recommended by TMDB viewers · both comedy

  5. Thunderstruck (2012)

    After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  6. Cadet Kelly (2002)

    Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.

    Why it matches: Recommended by TMDB viewers · both comedy

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  7. Rookie of the Year (1993)

    When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  8. The Geisha Boy (1958)

    Gilbert Wooley is a second-rate magician who is sent to entertain the troops in the pacific. During his time in Japan he becomes attached to a little orphan boy.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  9. Beckenrand Sheriff (2021)

    A lifeguard tries by all means to keep his home, an open-air swimming pool, from being closed.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  10. Adventures in Public School (2018)

    A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  11. Brain Donors (1992)

    Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit the rich widow and her scheming big-shot lawyer, who also wants to run the ballet.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  12. After the Ball (2015)

    After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. The Three Stooges (2012)

    Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the only home they've ever known to close, the trio sets out to raise $830,000 in one month. Out in the world for the very first time, the three innocent bumblers become embroiled in a murder plot and find stardom on a TV reality show.

    Why it matches: Recommended by TMDB viewers · both comedy

  14. Easy 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 this
  15. The Trouble with Angels (1966)

    Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Mr. 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 this
  17. Held 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

  18. How to Eat Fried Worms (2006)

    During the first day of his new school year, a fifth grade boy squares off against a bully and winds up accepting a dare that could change the balance of power within the class.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Barbie (2023)

    Barbie and Ken are having the time of their lives in the colorful and seemingly perfect world of Barbie Land. However, when they get a chance to go to the real world, they soon discover the joys and perils of living among humans.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. Scooby-Doo! and the Legend of the Vampire (2003)

    The Yowie Yahoo starts kidnapping musicians at a concert attended by Scooby and the gang in Vampire Rock, Australia.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this

Like Princess Sissy and something else?

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

Frequently asked questions

What are the best movies like Princess Sissy?

The closest matches to Princess Sissy are Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), A Burlesque on Carmen (1915) and Military Academy (2007). Below are 17 more, each with the reason it matches.

What should I watch after Princess Sissy?

Start with Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), the closest match to Princess Sissy.

What is the highest-rated movie like Princess Sissy?

Scooby-Doo! and the Legend of the Vampire (2003), rated 7.1/10 by 372 TMDB users.

What is the newest movie like Princess Sissy?

Barbie (2023) is the most recent release on this list.

Are there German movies like Princess Sissy?

Yes: Military Academy (2007) and Beckenrand Sheriff (2021).

How are movies similar to Princess Sissy chosen?

First come films that Trakt’s viewers watch alongside Princess Sissy, 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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