The Oscars, Hollywood’s most prestigious night, are renowned for their glitz, glamour, and predictability to some extent. However, throughout the history of the Academy Awards, there have been numerous instances where the expected outcome was overturned by a surprise win, leaving audiences and industry insiders alike stunned and thrilled. These unexpected victories have often defined the Oscars, adding an element of excitement and unpredictability to the ceremony. Let’s delve into some of the most unforgettable upsets in Oscar history.

  1. “Shakespeare in Love” (1998) Best Picture Win over “Saving Private Ryan” (1998)

Considered by many as one of the biggest upsets in Oscar history, “Shakespeare in Love” managed to clinch the Best Picture award over Steven Spielberg’s epic war drama “Saving Private Ryan.” Despite its critical acclaim and undeniable impact on cinema, “Saving Private Ryan” fell short, leaving audiences and critics alike astonished by the triumph of the romantic comedy-drama.

  1. Marisa Tomei’s Best Supporting Actress Win for “My Cousin Vinny” (1992)

In 1992, Marisa Tomei’s portrayal of Mona Lisa Vito in “My Cousin Vinny” earned her the Best Supporting Actress award. However, many were left in disbelief, considering her competition included veteran actresses like Vanessa Redgrave and Joan Plowright. Tomei’s win sparked controversy and fueled rumours of a mistake, but it remains one of the most surprising moments in Oscar history.

  1. “Crash” (2005) Best Picture Win over “Brokeback Mountain” (2005)

In 2006, the Academy shocked the world by awarding Best Picture to “Crash,” a film exploring racial tensions in Los Angeles, over the widely acclaimed “Brokeback Mountain,” directed by Ang Lee. While “Brokeback Mountain” was praised for its groundbreaking portrayal of a same-sex relationship, “Crash” emerged victorious, causing uproar and dividing opinions among critics and audiences.

  1. Adrien Brody’s Best Actor Win for “The Pianist” (2002)

Adrien Brody’s stunning performance as Holocaust survivor W?adys?aw Szpilman in “The Pianist” secured him the Best Actor award in 2003. However, his win was unexpected, given the stiff competition from industry heavyweights like Jack Nicholson and Daniel Day-Lewis. Brody’s emotional acceptance speech and genuine surprise further cemented his victory as one of the most memorable moments in Oscar history.

  1. “Moonlight” (2016) Best Picture Win over “La La Land” (2016)

In a jaw-dropping turn of events at the 2017 Oscars, “La La Land” was initially announced as the winner of Best Picture, only for the producers to realize midway through their acceptance speech that a mistake had been made. The award rightfully belonged to “Moonlight,” a poignant coming-of-age drama that resonated deeply with audiences. The unprecedented mix-up made headlines worldwide and remains one of the most unforgettable moments in Oscar history.

These surprise wins remind us that the Oscars are not immune to unpredictability and that excellence in filmmaking can sometimes defy expectations. While some upsets may spark controversy, they undoubtedly add excitement and intrigue to an already glamorous event. As we eagerly anticipate each year’s ceremony, we can only wonder what surprises the Oscars have in store for us next.