The Oscars have always been political and can be "gamed" by savvy studio heads. Remember when Weinstein got Shakespeare in Love to win Best Picture over Saving Private Ryan.
But in retrospect SIL isn't that bad of a movie, and has remained one of the few comedies that has won the best picture, and at least a token atonement for the many brilliant Shakespeare adaptations over the years (Including Kenneth Branagh's 1996 Hamlet) which the Academy has failed to adequately recognize.
The main problem with the Oscars is that it’s a trade guild award based on technical merit (at least in theory) that is marketed and televised as part Disney musical part standup comedy.
As a tech award, Best Picture should be given to films that have shown professional excellence in all departments: directorial, editing, cinematography, sound design, acting, etc. etc.
As a show, it should give out awards based on popularity and public reception (so, to blockbusters, horrors and romcoms).
Professional awards is what Cannes and Berlin film festival are, and that’s why you get obscure films showered with awards with little to no controversy: these don’t come with a 4-hour-long televised singing-and-dancing show marketed for general public.
And all this before we get into all the other problems like who are Academy members and voters, how big studios influence the vote, how politics come into play etc.
https://www.quora.com/Why-did-Shakespeare-in-Love-win-the-Be...