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 — How were the women (if any) portrayed? Were they the bosses of companies or girlfriends to male leads? According to a 2018 report by the Center for the Study of Women in Television and Film, women accounted for 36% of major characters in top grossing films. That gives you a little higher than a one-in-three chance of watching a movie with a female lead — why not increase the odds?
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 and figure out how to succeed in a man’s world. For every Mark Zuckerberg, there’s a Joy Mangano; for every Jerry Maguire, a J.C. Wiatt. Some women are based on real life personalities and some are completely fictional, but every single one broke gender barriers in the workplace and continue to inspire the next generation of strong and powerful women. (Don’t worry, no spoilers will be revealed.)
1. Joy (2015), Joy Mangano
Boss quote: “I want you to remember something, because a lot of times people get nice things and they start to think differently. We got here from hard work, patience and humility. So I want to tell you, don’t ever think that the world owes you anything, because it doesn’t. The world doesn’t owe you a thing.”
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 that’s also based on a true story. Ms. Mangano, played by the illustrious Jennifer Lawrence (who has signed on to play disgraced biotech entrepreneur Elizabeth Holmes in the upcoming movie, Bad Blood), starts off as a single mother who scrapes by as an airline booking agent. After her breakthrough invention — a self-wringing mop — Ms. Mangano navigates tricky business terrain in which betrayals abound, and allies become adversaries. But in the end, the woman this movie revolves around is the one true heroine we admire.
2. The Devil Wears Prada (2006), Miranda Priestly
Boss Quote: “Details of your incompetence do not interest me.”
Though she isn’t really an entrepreneur, she’s one of the most powerful and iconic bosses in recent movie history: the queen of all queens, Miranda Priestly. Played by a scathing Meryl Streep, Ms. 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 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 but powerful companies in movie history. Most remembered for her sharp wit and sarcasm, Ms. Priestly not only stays on top, but stays in style.
3. The Intern (2015), Jules Ostin
Boss quote: “It’s 2015, are we really still critical of working moms?”
How the tables have turned. Anne Hathaway, who played Miranda Priestly’s fashion-unsavvy assistant, plays Jules Ostin, an enthusiastic CEO and founder of About The Fit, a Brooklyn-based e-commerce fashion startup. In the span of eighteen months, she builds her startup from her own kitchen to a full-fledged company with more than 200 employees. Pair her with an old-school Robert DeNiro playing Ms. Ostin’s senior intern and you have a blossoming friendship packed with plenty of career advice. And if that doesn’t make you break out the popcorn, the movie portrays her husband, Matt, as a stay-at-home dad who gave up his career to take care of their daughter. Well done, Hollywood.
4. Chocolat (2000), Vianne Rocher
Boss quote: “Ah, good morning. Can I interest you in some nipples of Venus?”
Forget Johnny Depp — Juliette Binoche is the real star of this delectable movie as Vianne Rocher, an expert chocolatier who opens her own chocolate shop in a small orthodox French town. Part-time single mother part-time business owner, she does much more than sell chocolate, though. Over the course of the movie, her shop helps bring together families and empower individual women in spite of conservative challenges, and we can see the long-lasting effects of her business as Ms. Rocher uses her artisan craft to transform the town’s community for the sweeter. Tradition meets revolution: Ms. Rocher mixes together a dash of sumptuous romance, a sprinkle of entrepreneurial magic, and tops it off with everybody’s favorite chocolate chips.
5. Bridesmaids (2011), Annie Walker
Boss quote: “Help me, I’m poor.”
Single. In her mid-thirties. Losing her new bakery business. To most, Annie Walker may have hit rock bottom, but her story reflects that of many entrepreneurs in the economic recession. Ms. Walker (played by Kristen Wiig) hates her current deadbeat job as a sales clerk at a jewelry store, and we continually feel her pain of losing her business. Of course, that’s really not what this movie about — it’s meant to be a feel-good raunchy chick flick, the female equivalent of “The Hangover” about girlfriends finding new meaning in relationships and staying together through the thick of it all. The movie mostly hides Ms. Walker’s emotional wounds and vulnerabilities under running gags and slapstick jokes.But for all of its comedic glory, there are glimpses of one woman’s attempt to get her life back on track. And that’s something we all can relate to.
6. Sweet Home Alabama (2002), Melanie Smooter
Boss quote: “You know, I’ve really made something of myself. I have a career. People actually want to be me.”
Reese Witherspoon plays Melanie Smooter, a successful fashion designer in New York who has reinvented herself to hide her small-town Southern roots. Though the movie’s more interested in her love life than entrepreneurial ventures, there’s something in Ms. Smooter’s character that we don’t see enough in romantic comedies. She refuses to sacrifice her work for love (why should she be expected to, anyway?) and embodies the talent and ambition of a self-driven woman relentlessly following her dreams. Who cares about the drawling country men of the South and the McDreamies of New York? Melanie Smooter is the only character we should care about, and the only one we need in our life.
7. You’ve Got Mail (1998), Kathleen Kelly
Boss quote: “No one will ever remember you, Joe Fox. And maybe no one will remember me, either, but plenty of people remember my mother, and they think she was fine, and they think her store was something special. You are nothing but a suit!”
The next six movies are throwing it back to the 20th century, when women were just as badass as they are now. The first “oldie” is a bit of an underdog story that features Kathleen Kelly, the proud owner of the NYC-based bookstore, The Shop Around The Corner. Ms. Kelly, played by Meg Ryan, struggles to keep her family business afloat after a mega bookstore chain, Fox Books, moves in the neighborhood Though the movie takes a Shakespearean turn with the owners of the rival bookstores soon falling in love, Ms. Kelly’s fearless determination to overcome financial challenges, not to mention her incredible passion and dedication to her job, is one of the top selling points of this movie. Whether you find Ms. Kelly’s online relationship with a stranger heartwarming or alarming, watch this movie for her character alone. (Tom Hanks as a capitalist isn’t bad either.)
8. Steel Magnolias (1989), Truvy Jones
Boss quote: “Oh, sweetheart, don’t. Please don’t cry or I will too. I have a strict policy that nobody cries alone in my presence.”
In one of the earliest movies that put Julia Roberts on the map, she and the other four female main characters share the spotlight in this touching movie about a close-knit group of women getting through tough times. Truvy Jones, played by Dolly Parton, owns a hair salon in a small Louisiana suburb — it’s at the salon where the women meet by coincidence and the rest of the plot follows. In a movie where none of the men really matter, Truvy’s boss character marks a positive portrayal of women in business, and her leadership and responsibility in the group reminds us that, sometimes, we all need someone to lean on.
9. The Associate (1996), Laurel Ayres
Boss quote: “I’m going to perpetrate a great big whammy.”
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 financial analyst Laurel Ayres who is determined to break into the male-dominated world of investment banking. After getting passed for a promotion, Ms. 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, Ms. Ayres proves to be a successful independent stockbroker behind the man. If for nothing else, watch this to see Goldberg in a heavy pound bodysuit and how good her make-up job will be.
10. Baby Boom (1987), J.C. Wiatt
Boss quote: “Now look. There is nothing in the world to get uptight about. We are two summa cum laudes. We can handle one little baby for eight hours.”
Watch this if you love babies — a radiant Diane Keaton plays J.C. 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 gender discrimination. Will she accept demotion after demotion, or will she venture out to new business prospects? Without spoiling the end, there may or may not be baby applesauce involved. Whatever she decides to do, though, Ms. Wiatt represents the struggle of balancing personal and work lives and reminds us to thank our mothers more often.
11. Mildred Pierce (1945), Mildred Pierce
Boss quote: “Pack up, Bert.”
When your husband leaves you for another woman, what do you do? If you’re Mildred Pierce, you raise two daughters on your own and independently finance yourself through selling baked goods, waiting tables, and finally opening your own restaurant. Even if black-and-white films aren’t your thing, this crime-drama will leave you on the edge of your seat quietly cheering for Ms. Pierce, played by a stunning Joan Crawford. As her life takes a turn for worse at every corner, Ms. Pierce remains a strong-willed and empathetic character who wants the best for her children – as former wife, current mother, and successful entrepreneur, she gives hope to working women everywhere.
12. Lucy Gallant (1955), Lucy Gallant
Boss quote: “If you must wear boots, wear black with dark gray, not that color.”
Don’t let Hollywood’s 1950s chauvinist themes stop you from watching this gem: follow jilted-at-the-altar New Yorker Lucy Gallant, played by Jane Wyman, set up shop in a fictional Texas boom town and straddle the conflict between pursuing career and love. She runs her dress store out of a brothel, relies on loans from shady bankers, and is continually courted by a romantic interest, but Ms. Gallant’s journey from humiliated bride to fashion designer is, for lack of a better word, quite “gallant” indeed. If you know how old movies usually end, this one will be no surprise, but Ms. Gallant’s self-made path to success feels very true to life and inspires the entrepreneur within us all.