Think about the last movie you watched. It could be one of Netflix’s newest originals or a mainstream Hollywood flick currently showing in theaters.
Now think about whether the women portrayed — if any even were. Were they the bosses of companies, or girlfriends to male leads?
The movies on this list feature not just female leads, but female entrepreneurs and bosses who had to pull themselves up by their high-heel straps to navigate a man’s world. For every Mark Zuckerberg, there’s a Joy Mangano; for every Jerry Maguire, a J.C. Wiatt. Some of these women are based on real people, while others are completely fictional. But every single one broke gender barriers in the workplace, and they all continue to inspire the next generation of strong and powerful women.
Read on for the flicks that’ll give your next movie night a serious feminist upgrade. (And, don’t worry — no spoilers will be revealed.)
"Joy" (2015) – Joy Mangano
If you love rags-to-riches tales, this one’s for you. Delve into the makings of Joy Mangano’s million-dollar household industry empire — all based on a true story. Mangano, played by the illustrious Jennifer Lawrence, starts off as a single mother who scrapes by as an airline booking agent. After her breakthrough invention, a self-wringing mop, Mangano navigates a tricky business terrain in which betrayals abound, and allies become adversaries. Her journey to remain on top makes for a compelling watch.
"The Devil Wears Prada" (2006) – Miranda Priestly
With the film’s sequel coming out this year, how could we not reflect upon the queen? Played by a scathing Meryl Streep, Priestly is the editor-in-chief of the fictional fashion magazine, Runway — it’s widely speculated that her character was based on Anna Wintour, the former real-life editor of Vogue. When she’s not striking fear into all of her employees’ hearts, she’s juggling fashion shows, meeting with designers and building one of the most cutthroat-yet-powerful companies in movie history.
"The Intern" (2015) – Jules Ostin
Anne Hathaway, who played Priestly’s fashion-unsavvy assistant in the previous film on this list, plays Jules Ostin in this offering. Ostin is an enthusiastic CEO and founder of About The Fit, a Brooklyn-based e-commerce fashion startup. In the span of 18 months, she builds her brand into a full-fledged company with more than 200 employees. Paired with Robert DeNiro as her senior intern, the movie is as much about an unlikely friendship as it is about Ostin’s success. (Bonus: Her husband, Matt, is a stay-at-home dad who gave up his career to take care of their daughter.)
"Chocolat" (2000) – Vianne Rocher
Juliette Binoche stars in this delectable watch as Vianne Rocher, an expert chocolatier who opens her own shop in a small, religious French town. She splits her time between business ownership and single motherhood, selling sweets and offering insights to locals that help bring families together and empower townswomen. The film sees tradition meeting revolution: Rocher mixes together a dash of sumptuous romance, a sprinkle of entrepreneurial magic, and tops it off with everybody’s favorite, chocolate chips.
"Bridesmaids" (2011) – Annie Walker
Single. In her mid-thirties. Losing her new bakery business. To most, Walker may have hit rock bottom, but her story reflects that of many entrepreneurs. Walker, played by the hilarious Kristen Wiig, hates her current deadbeat job as a sales clerk at a jewelry store, and we continually feel her pain of her losing her business. The movie is, first and foremost, a feel-good raunchy chick flick, the female equivalent of “The Hangover.” But within its depths you find Walker’s vulnerabilities about her life and career. Indeed, for all of its comedic glory, there is also a tale about a woman coming back to her entrepreneurial passions.
"Sweet Home Alabama" (2002) – Melanie Smooter
Reese Witherspoon plays Smooter, a successful fashion designer from New York who reinvented herself to conceal her small-town Southern roots from her urban contemporaries. Though the movie is more interested in her love life than her work, there’s something in Smooter’s character that we don’t see enough in romantic comedies. She refuses to sacrifice her work for love, and her talent and ambition are defining traits. Who cares about the drawling country men of the South and the McDreamies of New York? Smooter’s pluck and craft are what we adore about this film.
"You’ve Got Mail" (1998) – Kathleen Kelly
Kelly, the emotional center of the film, is the proud owner of a New York City-based bookstore called The Shop Around The Corner. Played by the timeless Meg Ryan, Kelly struggles to keep her family business afloat after a bookstore giant, Fox Books, moves into the neighborhood. Though the movie takes a Shakespearean turn with the owners of the rival bookstores unwittingly falling in love, Kelly’s fearless determination to overcome various financial challenges, not to mention her incredible passion and dedication to her job, is among the top selling points of this movie.
"Steel Magnolias" (1989) – Truvy Jones
This touching movie about a close-knit group of women getting through tough times largely plays out in Jones’ hair salon, located in a small Louisiana suburb. Jones, played by Dolly Parton with lightness and love, is a grounding presence in this film that’s all about women (with their respective men taking a decided backseat). Jones’ leadership of, and responsibility to, everyone who enjoys a beauty day at her salon makes her one of the more beloved entrepreneurial female characters in film history.
"The Associate" (1996) – Laurel Ayres
If you set the movie “Tootsie” on Wall Street and switched Dustin Hoffman for Whoopi Goldberg, you would have the basic premise of “The Associate.” Goldberg plays Ayres, a financial analyst who is determined to break into the male-dominated world of investment banking. After getting passed over for a promotion, Ayres decides to start her own firm — as a white man. She dreams up the impossibly well-connected fictional persona of Robert S. Cutty as the face of the business, and with her own financial expertise as well the help of a complicit secretary, Ayres proves to be a successful, independent stockbroker.
"Baby Boom" (1987) – J.C. Wiatt
Watch this if you love babies — a radiant Diane Keaton plays Wiatt, a work-obsessed management consultant in Manhattan whose world gets turned upside down after inheriting a toddler. As she raises the baby on her own, she tries to climb the male-dominated corporate ladder and is faced with both the hardships of single motherhood and workplace gender discrimination. Will she accept demotion after demotion, or will she venture out to new business prospects? Either way, Wiatt represents the common struggle of work / life balance.
"Mildred Pierce" (1945) – Mildred Pierce
When your husband leaves you for another woman, what do you do? If you’re Pierce, you raise two daughters on your own and independently finance yourself by selling baked goods, waiting tables, and eventually opening your own restaurant. This crime-drama will leave you on the edge of your seat while cheering for Pierce, played by a stunning Joan Crawford. As her life takes numerous turns for the worse, Pierce remains strong-willed and empathetic – giving inspiration and hope to working women everywhere.
"Lucy Gallant" (1955) – Lucy Gallant
Gallant, a New Yorker who gets jilted at the altar, shifts course to set up shop in a fictional Texas boom town, where she straddles the conflict between career and love. Played by Jane Wyman, the shrewd and resourceful Gallant runs her dress store out of a brothel, relies on loans from shady bankers, and is continually courted by a romantic interest. Our protagonist’s journey from humiliated bride to fashion designer is, for lack of a better word, quite “gallant,” indeed.
"Like a Boss" (2020) – Mia Carter and Mel Paige
This modern-day film stars a trio of badass women: commanding actresses Tiffany Haddish, Rose Byrne, and Salma Hayek. Haddish and Byrne portray Carter and Paige, respectively, the co-owners of a beauty brand that’s put at risk by Hayek’s Claire Luna, a cosmetics mogul looking to steal their products and ideas to further grow her empire. Watching the film’s feature characters navigate the tough terrain of running a business together is as thrilling (to us, anyway) as any installment of the Fast & Furious franchise.
This post, updated for 2026, was first published in April 2019. Candice Helfand-Rogers contributed to the creation of this list.
