15 Classic Rags to Riches Movies

Pretty Woman and Maid in Manhattan are shoo-ins, but how about these other Cinderella stories?

We've gathered a collection of the best movies with a Cinderella story twist. There are the obvious choices (like Cinderella of course) but not all of the films are quite so straightforward.


Annie has remained ever-popular on Broadway and in three film adaptations. Based on the “Little Orphan Annie” comic strip from the 1920s, we’re partial to the 1982 version with Carol Burnett, Tim Curry, Bernadette Peters and Ann Reinking. The story of the little orphan who found her Daddy Warbucks is so iconic that Jay-Z sampled the musical soundtrack for his version of “Hard Knock Life.”


This 1979 film is one of the most beloved classic comedies, and turned stand-up comedian Steve Martin into a movie star, thanks to the guidance of director Carl Reiner. It’s a rags-to-riches-to-rags-to-riches tale following naive Navin Johnson on his first odyssey away from home. Some of the material definitely wouldn’t fly today, but it features Martin at his peak and the always winning Bernadette Peters.


The “hooker with a heart of gold” fable has never been better than in Garry Marshal’s 1990 rom com, Pretty Woman, which is more of a “vinyl boots to riches” story. Julia Roberts’ gleeful reactions to her newfound cash and her warm performance in the film made her a star. But with material wealth comes complications, especially in the transactional arrangement between Vivian and Edward. Fortunately, they manage to figure it out for the requisite happy ending.


The dark side of the American dream is captured in the immigrant story Scarface, a tale that’s been told with Italian immigrants in 1932, and Cuban immigrants in Brian DePalma’s 1983 version. There’s even a remake in the works with a Coen Brothers script and Diego Luna attached. But DePalma’s film is the gold standard, and the iconography and unforgettable dialogue have been permanently etched on pop culture. Al Pacino plays the cocaine-addled Tony Montana, who rises to the top the drug underworld in Miami, while Michelle Pfeiffer is the epitome of disco cool as his wife, Elvira. A cautionary tale about the perils and pitfalls of pursuing too much too fast.



Possibly the purest rags-to-riches film on this list, Danny Boyle’s Slumdog Millionaire swept the 2009 Oscars, collecting eight statuettes, including Best Picture. The story of a young man from the slums of Mumbai winning Who Wants To Be a Millionaire was a sleeper hit and cultural phenomenon and introduced the world to the dashing Dev Patel.


Struggling writer Eddie (Bradley Cooper) finds insta-success in one little pill in Limitless, unlocking the full power of his brain and using it to earn a fortune in the stock market. Of course, there are some side effects, but [spoiler alert], Eddie manages to make NZT-48 work for him, not the other way around. But we all know success from a pill only happens in the movies.


This 2002 rom com stars Jennifer Lopez and Ralph Fiennes as a hotel maid and a politician who fall in love, thanks to a high-end fashion transformation. Cinderella herself knew the power of a killer pump, and that tale is repeated here as Lopez, playing maid Marisa, accidentally falls in love with a Senate candidate while trying on a Dolce & Gabbana coat and passing as a hotel guest.


This modern take on Mark Twain’s story The Prince and the Pauper starring Eddie Murphy and Dan Aykroyd was a huge comedy hit in 1983. A street hustler (Murphy) and a silver-spoon-fed commodities broker (Aykroyd) become the subject of a nature vs. nurture experiment to see how each one fares in each other’s lives. Turns out the street hustler is perfectly primed for commodities trading. The combination of comedy and social commentary proves to be the right formula for crafting a timeless hit.


Will Smith starred with son Jaden (in his screen debut) in the true story of Chris Gardner, an entrepreneur who risked it all, even becoming homeless with his young son, while competing with other unpaid interns for a top-level brokerage position. The lesson he imparts to his young son throughout all of their trials is that, if “you want something? Go get it.” Adding even more shine to the inspirational true-life tale? Will Smith was nominated for an Academy Award for his performance.



Beloved writer Roald Dahl wrote, “Charlie and the Chocolate Factory” in 1964, the tale of young Charlie Bucket, who wins a chance to visit the fantastical candy factory of Willy Wonka. The term “golden ticket” has even become synonymous with the notion of a lucrative lifeline or quick fix. Tim Burton’s 2005 film starring Johnny Depp has some weird and quirky charms, but nothing beats the warmth that Gene Wilder brings to the Wonka role in the 1971 film Willy Wonka and the Chocolate Factory.


Paul Thomas Anderson is a master of capturing distinctly American tales about the intertwining paths of ambition and tragedy, and his 2007 masterpiece There Will Be Blood is his starkest film on this subject. Daniel Day-Lewis is transformed as oil man Daniel Plainview, who strikes black gold in California during the oil rush. Based on the novel “Oil!” by Upton Sinclair, There Will Be Blood is a fevered exploration of manifest destiny, the dark side of the American dream, and the dangers of greed. Also, we’ll never think about milkshakes the same way again.


Evelyn Waugh’s 1945 novel has been adapted into a mini-series starring Jeremy Irons in 1981, and a film version in 2008 starring Matthew Goode and Emma Thompson. The story follows Charles Ryder as he explores the world of English aristocracy and landed gentry while visiting his college bud at the family castle. Intimate intrigue ensues with both Sebastian and his sister, and the story is a tribute to the dying system of the noble but troubled English aristocracy, as seen through the eyes of an outsider.


F. Scott Fitzgerald was a great documenter of the lavish lives of the rich as he lived and observed them during the roaring ‘20s, living high on the hog and bathtub gin from New York to Europe and back again. The Great Gatsby is his magnum opus on the topic, wherein Nick Carraway watches the goings on of the mysterious Jay Gatsby and his love, Daisy, during their wild Long Island soirees.



“Rags to riches” films are more often than not referred to as “Cinderella stories,” so we had to include the fairy tale on this list. The animated Disney version from 1950 has undeniable staying power, and the 2015 live-action version of the story starring Lily James rekindled our appreciation for the fairy tale. Now if only we all had a fairy godmother to say “Bippity Boppity Boo!"


The story of Facebook is one of the most fascinating tales of 21st-century rapid rises to fame and fortune, especially as depicted in David Fincher’s 2010 film starring Jesse Eisenberg as Mark Zuckerberg. As they say, The Social Network has everything: Harvard clubs, litigious twins, Justin Timberlake, and more. The IRL drama is way better than anything you might find online.

This story originally appeared on Townandcountrymag.com.
* Minor edits have been made by the Townandcountry.ph editors.

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