#24: Shakespeare in Love, 71st Academy Awards, 1999

Categories: Winner of 7 Academy Awards, Including Best Picture and Best Actress

Best Picture nominees who lost at the 71st Academy Awards:

• Elizabeth
• Life is Beautiful
• Saving Private Ryan
• The Thin Red Line

In isolation, Shakespeare in Love may have seemed like a harmless historical romance, whimsically reimagining the love life of the Bard himself. Yet, when it swept the 71st Academy Awards, its victory felt less like a triumph of cinematic excellence and more like a calculated scheme to snag Oscar gold.

From its theatrical debut, Shakespeare in Love was accompanied by an aggressive Oscar campaign strategically aimed at tarnishing the reputation of its formidable competitor, Saving Private Ryan. These underhanded tactics secured its victory and set a precedent for future awards season maneuvers. However, as time passed, the glitter of its accolades faded, revealing the film’s true mediocrity and nullifying whatever merits it may have claimed.