1999 was a weird year at the Academy Awards (the Awards were held in 1999, but the movies were all from 1998). It’s famous because it holds perhaps the most Oscar upsets of any year, and they all revolve around two films: Saving Private Ryan and Shakespeare In Love.
The biggest movie of 1998 was Steven Spielberg’s incredible World War II epic starring Tom Hanks, Saving Private Ryan. It won over movie critics, war veterans, and the general public to amass more than $200 million domestically with its incredibly realistic portrayal of combat, camaraderie, and the effects of war on the soldiers that fought during World War II.
Saving Private Ryan picked up 11 Oscar nominations and many believed that it would become the overall Awards champion of the year by predicting victories in 3 major categories: Best Actor in a Lead (Tom Hanks) Role, Best Director, and Best Picture.
However, this was not to be as the romantic comedy Shakespeare In Love remakably surpassed the Spielberg’s war epic in not only Academy Award nominations, but incredulously in Academy Awards wins! The dark horse of 1998 went on to win seven Oscars beating out Saving Private Ryan (which surprised everyone by only winning five) and every other movie of the year.