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.
Shakespeare In Love became an underdog powerhouse that night and claimed surprise victories in four more major categories. Gwyneth Paltrow won the Oscar for Best Actress in a Lead Role despite most people expecting Cate Blanchett to win for her brilliant performance as Queen Elizabeth I in the film Elizabeth (Blanchett won the Best Actress awards at the Golden Globes and BAFTA Awards). And perhaps even more surprising was Judi Dench’s win for Best Actress in a Supporting Role over major contender Kathy Bates (Primary Colors), despite Dench’s only being in Shakespeare In Love for just eight minutes.
After Shakespeare In Love swept swept the Actress categories everyone assumed that Saving Private Ryan would get its dues with Tom Hanks winning for Best Actor in a Lead Role and then Best Picture. Certainly an amazing actor like Tom Hanks would win, especially with perennial upsetter Shakespeare In Love having no representation in the Best Actor category. Maybe chalk it up to Saving Private Ryan having a bad day, but it was denied another award as Roberto Benigni was called as the winner for Best Actor for his role in Life Is Beautiful.
The Academy may have been hoping by picking Benigni that he would do something even more ridiculous than his entrance after winning for Best Foreign Film.
But the biggest (and most controversial) surprise was yet to come. After Shakespeare In Love earned the Oscar for Best Original Screenplay, everyone figured Saving Private Ryan would win for Best Picture since it won for Best Director, but everyone was stunned when presenter Harrison Ford announced Shakespeare In Love as the winner for Best Picture to end the night. This is debatebly the biggest Oscar upset in history (with perhaps exception to 1942 when How Green Was My Valley won Best Picture over Citizen Kane). It was so stunning that some still call this unexpected victory an “Academy Awards mistake” as compared to an “Academy Awards upset,”making the 1999 Awards show one of the most surprising shows in Oscar history and forever solidifying it as the most debated year of the Awards.