Holiday (1938); starring Katherine Hepburn and Cary Grant; directed by George Cukor.
The Short Version
There are people in this world that will not enjoy Holiday, but you probably shouldn’t be dating them.
The Plot in a Nutshell
Cary Grant is a charming up-and-comer who has worked from childhood. He falls in love with a girl from a rich family (Doris Nolan), but things begin to go awry when he announces that—now that he has accumulated sufficient funds—he plans to stop working. He finds kindred spirits in his fiancée’s acerbic, eccentric sister Linda (Hepburn) and her dissolute but delightful brother (Lew Ayres). Complications—and back-flips—result.
The Reason You (and Your Gentleman/Lady Friend) Will Love It
A few years back Chloe Angyel, while working on a dissertation providing a feminist analysis of romantic comedies, wrote a great piece discussing why rom-coms are still important—both despite and because of their failings. I encourage you to read the whole thing if you haven’t already, but here’s a key excerpt:
It's easy to dismiss romantic comedies as fluffy, mindless cinematic dreck, and some of them are just that. In every genre there are some well-made movies, and many more middling and awful ones….It is true that in the last few years, the awful rom coms seem to outnumber the good ones, but that's not why people love to hate romantic comedies. They love to hate them because they're "chick flicks," made for and about women.
Holiday smashes through those assumptions. Sure, it's extremely successful as a classic rom-com: there’s gorgeous Cary Grant (that jaw! that smile!) and beautiful Katherine Hepburn (that hair! that accent!) exchanging witty barbs faster than the Gilmore Girls; there’s the delightful supporting cast full of hilarious eccentrics; and there’s the feeling of rightness that comes from watching the characters not only fall in love, but also, more importantly, find the unique safety found in the friendship of a kindred spirit.
But—and here’s the thing that makes Holiday tower over its competition—it’s also an extraordinarily successful piece of political commentary. This is a movie with a radical agenda, and that agenda isn’t particularly hidden. It’s a movie about labor, and capitalism, and the logic of work. Why must we work so hard? Why is work the way we structure our lives? Does it have to be that way?
Holiday was made during the Great Depression, and it was a commercial failure (there’s been some speculation that people during the Depression had no desire to watch a man trying to escape work when they were searching desperately to find it). I watched it for the first time in 2009, a few months after the beginning of the financial crisis. It could have been a new release—there’s even a joke about the terrible business decisions of General Motors. Holiday is as relevant today as it was seventy-five years ago.
This is the movie that will remind you why you love romantic comedies, if you already watch them, or the movie that will make you give them a second look if you don’t. It combines all the best parts of a rom-com with all the best parts of a high-brow political film, and it does it all with a backflip.