#12: Holiday (1938)
In Holiday, Cary Grant plays Johnny Case, a self-made striver who shocks high society by announcing he wants a break from work before settling into marriage. Katharine Hepburn shines as Linda Seton, the sharp and restless sister who understands his rebellion against her family’s rigid world. Directed by George Cukor and adapted from Philip Barry’s stage play, the film unfolds inside lavish Park Avenue interiors that mirror the privilege under scrutiny. Critics applauded Grant’s and Hepburn’s effortless rhythm and wit.

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