I'll include the IMDb synopses for each film, so you don't need to have seen any of them to play. Just pick the one that interests you the most! In fact, I recommend doing this instead of just choosing the films you've already seen.
I think we'd all get exhausted by a ~20 round game, so this game will only cover winners through the 1960s. There will (maybe, eventually) be a second game for the New Hollywood era and beyond once this one is finished.
ROUND ONE
1. Wings (1927): Two young men, one rich, one middle class, who are in love with the same woman, become fighter pilots in World War I.
2. The Broadway Melody (1929): A pair of sisters from the vaudeville circuit try to make it big time on Broadway, but matters of the heart complicate the attempt.
3. All Quiet on the Western Front (1930): A young soldier faces profound disillusionment in the soul-destroying horror of World War I.
4. Cimarron (1931): A newspaper editor settles in an Oklahoma boom town with his reluctant wife at the end of the nineteenth century.
5. Grand Hotel (1932): A group of very different individuals staying at a luxurious hotel in Berlin deal with each of their respective dramas.
6. Cavalcade (1933): The triumphs and tragedies of two English families, the upper-crust Marryots and the working-class Bridges, from 1899 to 1933 are portrayed.
**
PARENTS AND FIRSTBORN
If you chose:
1 (Wings):
Parents have the initials KA(D)Y and HN(M)A.
Their first child is a son. He has one name that is aviation-related, one name inspired by either parent, and an optional third name from the US top 25 for 1927. These may be in any order.
2 (Broadway Melody):
Parents have the initials CK(L)Z and FU(G)M.
Their first child is a daughter. She has one name that is music-related, one name inspired by either parent, and an optional third name from the US top 25 for 1929. These may be in any order.
3 (All Quiet):
Parents have the initials PF(B)E and VL(T)D.
Their first child is a son. He has one name that is military-related, one name inspired by either parent, and an optional third name that is more commonly used as a surname. These may be in any order.
4 (Cimarron):
Parents have the initials HA(K)L and LL(A)R.
Their first child is a daughter. She has one name that is western-themed, one name inspired by either parent, and an optional third name inspired by nature. These may be in any order.
5 (Grand Hotel):
Parents have the initials TP(C)C and AK(I)O.
Their first child is a son. He has one name that is German, one name inspired by either parent, and an optional third name that is also a place name. These may be in any order.
6 (Cavalcade):
Parents have the initials DP(D)G and KO(R)F.
Their first child is a daughter. She has one name that is traditional English, one name inspired by either parent, and an optional third name that is ancient or medieval. These may be in any order.