Holiday marked Katharine Hepburn’s Hollywood comeback, and for good reason– she’s the best out of the cast, she’s downright magnetic, and her dynamic with Cary Grant is effortlessly compelling. All of these elements would have made a standard romcom work. However, there’s more to Holiday than what meets the eye. Underneath this droll comedy of manners is a sadness that lies in the wealthy family it’s poking fun at, and that melancholy proved to be a more potent critique, as the riches they can’t help but acquire couldn’t help fill the emptiness left with their mother’s death and couldn’t free them to do what they truly wanted to do. Holiday might not have resonated with audiences during the Great Depression, but it nonetheless makes for a surprisingly profound classic about personal freedom.