The Philadelphia Story (1940)
The Philadelphia Story was originally a Broadway hit turned silver screen hit. This stars the greatest of the greats: Katharine Hepburn, James Stewart, and Cary Grant. This incredible trio received tons of accolades for their roles in this film.
The story follows a wealthy Philadelphia socialite (Hepburn) who is splitting from her husband (Grant). She prepares to marry another man when she gets mixed up with her ex-husband and a reporter (Stewart). She's got a lot of options!