Movies Like Cross-Dressed and Punished

If you liked Cross-Dressed and Punished (2000), a movie directed by Chelsea Pfeiffer, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
A Room with a View (1986)
★ 6.9/10
When Lucy Honeychurch and chaperon Charlotte Bartlett find themselves in Florence with rooms without views, fellow guests Mr Emerson and son George step in to remedy the situation. Meeting the Emersons could change…
2
Mary Poppins Returns (2018)
★ 6.5/10
Mary Poppins returns to the Banks family and helps them evade grave dangers by taking them on magical, musical adventures.
3
Nanny McPhee and the Big Bang (2010)
★ 6.3/10
Nanny McPhee appears at the door of a harried young mother who is trying to run the family farm while her husband is away at war. But once she’s arrived, Nanny discovers that the children are fighting a war of their…
4
Nightfall (1956)
★ 6.9/10
An innocent man turns fugitive as he reconstructs events that implicate him for a murder and robbery he did not commit.
5
Tinker Bell and the Lost Treasure (2009)
★ 6.8/10
A blue harvest moon will rise, allowing the fairies to use a precious moonstone to restore the Pixie Dust Tree, the source of all their magic. But when Tinker Bell accidentally puts all of Pixie Hollow in jeopardy, she…
6
The War with Grandpa (2020)
★ 6.4/10
Peter is thrilled that his Grandpa is coming to live with his family. That is, until Grandpa moves into Peter's room, forcing him upstairs into the creepy attic. And though he loves his Grandpa, he wants his room back…
7
Tangled: Before Ever After (2017)
★ 6.8/10
Rapunzel grapples with the responsibilities of being a princess and the overprotective ways of her father. While she wholeheartedly loves Eugene, Rapunzel does not share his immediate desire to get married and settle…
8
Uptown Girls (2003)
★ 7.1/10
Molly Gunn, the freewheeling daughter of a deceased rock legend, is forced to get a job when her manager steals her money. As nanny to Ray - the precocious, oft-ignored daughter of a music executive - she learns what…
9
The First Wives Club (1996)
★ 6.7/10
After years of helping their hubbies climb the ladder of success, three mid-life Manhattanites have been dumped for a newer, curvier model. But the trio is determined to turn their pain into gain. They come up with a…
10
Niagara (1953)
★ 6.8/10
Rose Loomis and her older, gloomier husband, George, are vacationing at a cabin in Niagara Falls. The couple befriend Polly and Ray Cutler, who are honeymooning in the area. Polly begins to suspect that something is…
11
Think Like a Man (2012)
★ 6.8/10
The balance of power in four couples’ relationships is upset when the women start using the advice in Steve Harvey’s book, Act Like A Lady, Think Like A Man, to get more of what they want from their men. When the men…
12
Dennis the Menace (1993)
★ 5.9/10
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…
13
Educating Rita (1983)
★ 6.9/10
Rita, a witty 26-year-old hairdresser, wants to 'discover' herself, so she joins the Open University where she meets the disillusioned professor of literature, Dr. Frank Bryant. His marriage has failed, his new…
14
How to Lose a Guy in 10 Days (2003)
★ 6.9/10
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and…
15
The Dead (1987)
★ 6.9/10
After a convivial holiday dinner party, things begin to unravel when a husband and wife address some prickly issues concerning their marriage.
16
What's Eating Gilbert Grape (1993)
★ 7.7/10
Gilbert Grape is a small-town young man with a lot of responsibility. Chief among his concerns are his mother, who is so overweight that she can't leave the house, and his mentally impaired younger brother, Arnie, who…
17
Caught (1949)
★ 6.6/10
Wide-eyed and poor young Leonora weds an obsessive millionaire named Ohlrig, but the marriage is loveless. Even worse, Ohlrig seems to have manic, violent tendencies. Eventually, young Leonora escapes her unhappy life…
18
Mrs. Harris Goes to Paris (2022)
★ 7.3/10
A 1950s London cleaning lady falls in love with an haute couture dress by Christian Dior and decides to gamble everything for the sake of this folly.
19
He's Just Not That Into You (2009)
★ 6.6/10
Remember that really cute girl/guy who said they'd call – and didn't? Maybe they lost your number. Maybe they're in the hospital. Maybe they're awed by your looks, brains or success. Or maybe... They're just not that…
20
Shrek 2 (2004)
★ 7.3/10
Happily ever after never seemed so far far away when a trip to meet the in-laws turns into a hilariously twisted adventure for Shrek and Fiona. With the help of ever-faithful Donkey, Shrek takes on the potion-brewing…