Shakespeare in Love's Best Picture win was heavily controversial, to put it mildly. In the years since it took home this trophy, only Crash and Green Book seem to have generated equal or greater amounts of strife with their respective Best Picture wins. Its controversial award season campaign tactics, as well as the fact that it beat out a Steven Spielberg directorial effort for the award, not to mention the very understandable dark cloud that lingers on anything, like a Best Picture win, that gave the monstrous Harvey Weinstein further clout in Hollywood all, have led the reputation of Shakespeare in Love to suffer greatly. In recent years, though, its standing seems to have improved significantly as Oscar snubs and wins fade further into the past and we're all left to just take a look at the movie on its own merits.
