Movies Like The $50,000,000 Cherry

If you liked The $50,000,000 Cherry (1987), a movie directed by John T. Bone, 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
The Heiress (1949)
★ 7.8/10
In 1840s New York, the uneventful and boring days of the daughter of a wealthy doctor come to an end when she meets a dashing poorer man — who may or may not be after her inheritance.
2
A Funny Thing Happened on the Way to the Forum (1966)
★ 6.1/10
A wily slave must unite a virgin courtesan and his young smitten master to earn his freedom.
3
Lust for a Vampire (1971)
★ 5.9/10
In 1830, the Karnstein heirs use the blood of an innocent to bring forth the evil that is the beautiful Mircalla - or as she was in 1710, Carmilla. The nearby Finishing School offers rich pickings not only in in the…
4
The Age of Innocence (1993)
★ 7/10
In 19th century New York high society, a young lawyer falls in love with a woman separated from her husband, while he is engaged to the woman's cousin.
5
American Pie (1999)
★ 6.7/10
At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a…
6
Love & Friendship (2016)
★ 6.1/10
From Jane Austen’s novella, the beautiful and cunning Lady Susan Vernon visits the estate of her in-laws to wait out colorful rumors of her dalliances and to find husbands for herself and her daughter. Two young men…
7
Elvira: Mistress of the Dark (1988)
★ 6.7/10
Arriving in the small town of Fallwell, Massachusetts to claim her inheritance, horror hostess Elvira receives a less than enthusiastic reception from the conservative locals, including her sinister uncle Vincent.
8
The Importance of Being Earnest (2002)
★ 6.8/10
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
9
Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972)
★ 6.5/10
A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and…
10
The Grass Is Greener (1960)
★ 6.4/10
Victor and Hillary are down on their luck to the point that they allow tourists to take guided tours of their castle. But Charles Delacro, a millionaire oil tycoon, visits, and takes a liking to more than the house…
11
The Most Hated Woman in America (2017)
★ 6.2/10
The true story of Madalyn Murray O'Hair -- iconoclast, opportunist, and outspoken atheist -- from her controversial rise to her untimely demise.
12
Anastasia (1956)
★ 6.8/10
Russian exiles in Paris plot to collect ten million pounds from the Bank of England by grooming a destitute, suicidal girl to pose as heir to the Russian throne. While Bounin is coaching her, he comes to believe that…
13
The Countess (2009)
★ 5.9/10
Kingdom of Hungary, 17th century. As she gets older, powerful Countess Erzsébet Báthory (1560-1614), blinded by the passion that she feels for a younger man, succumbs to the mad delusion that blood will keep her young…
14
The Last American Virgin (1982)
★ 6.6/10
The friendship of a group of young friends struggling with teen sex, drugs, and work is jeopardized by a romantic interest which may turn pals into bitter rivals.
15
The 40 Year-Old Virgin (2005)
★ 6.4/10
Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers…
16
Winter's Tale (2014)
★ 6.3/10
A burglar falls for an heiress as she dies in his arms. When he learns that he has the gift of reincarnation, he sets out to save her.
17
The Moon Is Blue (1953)
★ 6.3/10
Two aging playboys are both after the same attractive young woman, but she fends them off by claiming that she plans to remain a virgin until her wedding night. Both men determine to find a way around her objections.
18
The Brothers Bloom (2009)
★ 6.6/10
The Brothers Bloom are the best con men in the world, swindling millionaires with complex scenarios of lust and intrigue. Now they've decided to take on one last job – showing a beautiful and eccentric heiress the time…
19
Bad Sister (2015)
★ 6.6/10
As a top student at St. Adeline's Catholic Boarding School, Zoe senses that something is not quite right about the school's new nun-- a sense proven to be true when it is revealed the "good' nun is an imposter with a…
20
The Vampire Lovers (1970)
★ 6.4/10
In the heart of Styria the Karnstein Family, even after their mortal deaths, rise from their tombs spreading evil in the countryside in their lust for fresh blood. Baron Hartog whose family are all victims of Karnstein…