‘You Can’t Take it With You’ (1938)
If you look through the list of Best Picture winners to see which are cultural icons and which have fallen by the wayside, generally the comedies fare worse. Comedy struggles to hold up over time the way that drama does. “You Can’t Take it With You” fits that pattern. It’s a comedy of manners about a rich family having to deal with a poorer family when they’re drawn together via an engagement.