5. 1998: Shakespeare In Love vs. Steven Spielberg & Saving Private Ryan
The Academy makes big mistakes often. Most famously, it rewarded John Ford's How Green Was My Valley the Best Picture win over the most beloved film of all time, Citizen Kane. In 1998, the Academy made one of their biggest blunders to date, awarding the slapstick filled mediocre romantic comedy Shakespeare in Love over Spielberg's Saving Private Ryan. Although Spielberg walked home with the Best Director award, a feat incredibly deserved and obvious to anyone who's seen both films, his movie did not manage to win Best Picture. Why is this? One reason is that the studio backing Shakespeare in Love had bombarded Hollywood with a smear campaign against Spielberg's World War II epic, claiming that, among other things, many of its scenes were too historically inaccurate to be considered worthy of merit. Let's think of that. The people behind Shakespeare in Love thought Saving Private Ryan was too full of historical inaccuracies. The Academy Awards that year were proof that the world is a stupid, stupid place.