By: Renee Grant

On Sunday, February 26th, we’ll all be watching the 89th Annual Academy Awards and hoping our favorites win an Oscar statue. Over the years,  there have been fashion faux pas, upset wins, and so many other memorable moments.

It’s hard to narrow down the most shocking seconds in Oscar history to just five, but a few still have jaws dropping. Check out this list and add your own in the comments, on our Facebook page, or talk to us on Twitter!

  • Hattie McDaniel becomes the first Black woman to win an Oscar (1940) – Perhaps the first most shocking Oscar moment in history, Hattie McDaniel accepted her Oscar for her role as Mammy, a slave on a Georgia plantation in the film Gone With The Wind. Although McDaniel was able to accept her award on stage, the scourge of segregation kept the first Black woman ever to win an Academy Award from sitting in the front of the theater where she accepted her plaque. It took 51 years until another Black woman would win the golden prize when Whoopi Goldberg won as Best Supporting Actress in the movie Ghost.

  • Sidney Poitier becomes the first Black man to win an Oscar: (1964) – When Sidney Poitier won his Oscar in 1964 it was still a controversial time for people of color to take the stage and accept such a prestigious honor. Poitier won for his role as Homer Smith in Lilies of the Field. Speaking of that win as an honorary Oscar recipient in 2002, Poitier said of that moment, “It represented progress. It meant the embracing of a kind of democracy that had been very long in maturing.”

  • Barbra Streisand shares her win with Katherine Hepburn (1969) – Today, we’ll probably never see an actress share a win for a top honor again; at the time, it was pretty controversial. Barbara basked in the glow that night, accepting the Oscar for her turn in the film Funny Girl. Hepburn, who won for her role in the movie The Lion in the Winter, didn’t show. Due to Hepburn’s absence, Streisand shined and the moment no doubt advanced her already burgeoning career. Bonus: Babs’ speech and outfit when she accepted the award!

  • Marlon Brando takes a social stance (1973) – Marlon Brando made his mark on the Academy Awards by refusing to attend the ceremony in an act of social defiance the first Hollywood heavyweight to use the platform with an objective of bringing awareness to subjects outside of the ceremony. Brando sent a Native American activist, Sacheen Littlefeather, to accept on his behalf.

  • Cher’s dress is barely there for her Oscar win (1988) – Cher has always been known for her wild and free personality, reflected in her daring outfits over the years. In the 80’s everything was excessive, including the show of skin. Cher went “there” with her ultra-sheer spider web-inspired couture ensemble worn during her 1988 win for her portrayal of Loretta Castorini in the hit film Moonstruck. Notably? Cher beat out the almost unconquerable Meryl Streep that year for the statue. Bonus: Cher completed her acceptance speech with just one earring, presumably losing the other during a trip over her shawl during her walk to the stage.

What are your favorite Oscar moments?


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