Holiday

1938 George Cukor comedy starring Cary Grant and Katherine Hepburn was a follow-up to the success Grant and Hepburn had with Bringing Up Baby.

Free-thinking, happy-go-lucky Grant is enaged to an heiress but when he begins to question the meaning of his life he finds he has much more in common with her spirited sister (Hepburn).

Smart writing, great cast, and very funny screwball comedy.

http://www.imdb.com/title/tt0030241/