1. Citizen Kane, 1941
Orson Welles’s cinematic masterpiece follows a newspaper tycoon at the turn of the 19th century, offering a cautionary—and still relevant—look at the perils of turning your back on the workers who’ve helped build your empire.
"If I hadn’t been very rich, I might have been a very great man."
2. The Apartment, 1960
Set in the Rolodex-spinning, martini-swilling world of a 31,000-employee 1950s insurance colossus, Billy Wilder’s insightful look at brutal workplace misogyny and the perils of ladder climbing is by turns funny and devastating.
"Some people take and some people get took."
3. Willy Wonka & the Chocolate Factory, 1971
Innovation meets marketing genius when an idiosyncratic candy entrepreneur (Gene Wilder)—a sort of psychedelic proto Elon Musk—creates an international frenzy with a stunt that will admit five lucky fans to his moonshot factory.
"We are the music makers, and we are the dreamers of dreams."
4. 9 to 5, 1980
Jane Fonda, Lily Tomlin, and Dolly Parton play women suffering under a jerky boss at a generic company in this hilarious—but also pointed and prescient—look at casual office sexism.
"I am your employee and as such I expect to be treated equally, with a little dignity and a little respect!"
5. Broadcast News, 1987
James L. Brooks’s sharp romantic comedy—with Holly Hunter as a top TV producer—explores painful realities of office politics and relationships, all set against the extremely stressful world of the news business.
"Wouldn’t this be a great world if insecurity and desperation made us more attractive?"
6. Glengarry Glen Ross, 1992
Adapted by David Mamet from his Pulitzer Prize–winning play, this bleak vision of business at its most gritty tracks salesmen (Al Pacino, Jack Lemmon, and other greats) as they scramble to survive in the brutal world of low-end real estate.
"A-B-C. A: Always. B: Be. C: Closing. Always be closing. Always be closing."
7. Office Space, 1999
In Silicon Valley creator Mike Judge’s brilliantly detailed take on cubicle-culture malaise, a programmer (Ron Livingston) exacts revenge on his tech-company employer.
"Um . . . I’m gonna need you to go ahead and come in tomorrow. So if you could be here around 9 that would be great, mmkay?"
8. The Devil Wears Prada, 2006
A young journalist (Anne Hathaway) scores a spot as an assistant to the most terrifying fashion magazine editor (Meryl Streep), who teaches her about life, work, and the unexpected complexity of blue sweaters—or was that cerulean?
"She’s not happy unless everyone around her is panicked, nauseous, or suicidal."
9. The Social Network, 2011
David Fincher and Aaron Sorkin recast Facebook’s sunny founding myth as a white-knuckled morality tale, depicting Mark Zuckerberg (Jesse Eisenberg) as a coding savant in denial about his personal demons.
"You’re not an asshole Mark, you’re just trying so hard to be."
10. Straight Outta Compton, 2015
Drug dealer Eazy-E (Jason Mitchell) taps his profits and business savvy to form a world-changing rap group and record company with Dr. Dre, Ice Cube, and other friends. In F. Gary Gray’s emotional rags-to-riches N.W.A. biopic, contracts are as ruthless as gangbangers.
"I told you not to sign that shit, Dre."
[Illustration Source Images: Todd MacMillan, Universal Pictures, Everett Collection (Straight Outta Compton, 2015); 20th Century Fox, Everett Collection (The Devil Wears Prada, 2016; 9 to 5, 1980); Everett Collection (Willy Wonka & the Chocolate Factory, 1971); Columbia Pictures, Everett Collection (The Social Network, 2010)]
A version of this article appeared in the September issue of Fast Company magazine.