The glam, the gags, and the goops!
(L-R) Adrien Brody and Halle Berry; Heath Ledger and Jake Gyllenhaal; Lady Gaga; Fred Berger and Mahershala Ali.
Brian Vander Brug/Los Angeles Times via Getty Images; Focus Features; Kevin Winter/Getty Images; Al Seib/Los Angeles Times via Getty Images
97 years later, it comes as no surprise that there have been a lot of wild and chaotic moments in the history of the Academy Awards.
Regarded as "Hollywood's Biggest Night," the Oscars have had plenty of easily predicted winners, and also mind-blowing surprises.
While it is increasingly challenging to perfectly predict who will win an Oscar at any given year, viewers can always count on the glam, the gags, and the goops delivered by the Academy Awards.
Keep scrolling to check out some of the biggest gags and chaotic wins in the history of the Academy Awards — and tune in to watch the 2025 Oscars this Sunday, March 2.
'Moonlight' wins Best Picture over 'La La Land' at the 2017 Oscars.
'La La Land' producer Fred Berger congratulates 'Moonlight' actor Mahershala Ali at the 2017 Academy Awards.
Al Seib/Los Angeles Times via Getty Images
Widely considered the most chaotic Oscars moment of all time, the 2017 Academy Awards ceremony had Bonnie & Clyde stars Faye Dunaway and Warren Beatty announcing the award for Best Picture.
Due to an envelope mix-up, La La Land was named the winner. A few minutes later, the crew of La La Land called the Moonlight crew to accept the award, as it was revealed by producers that Moonlight had won the Oscar for Best Picture — not La La Land!
'Crash' wins Best Picture over 'Brokeback Mountain' at the 2006 Oscars.
(L-R) Official poster for 'Crash'; Official poster for 'Brokeback Mountain.'
Ang Lee's film is still widely considered one of the best movies of all time by many critics. On the other hand, Crash is infamously remembered as one of the worst-ever Best Picture winners ever. Still, the Academy couldn't help but award this maudlin tale of racism and redemption.
'Shakespeare in Love' wins Best Picture over 'Saving Private Ryan' at the 1999 Oscars.
(L-R) Gwyneth Paltrow, Judi Dench, James Coburn, Roberto Benigni at the 1999 Academy Awards.
HECTOR MATA/AFP via Getty Images
The 71st Academy Awards featured this surprising Best Picture winner, and also gave Gwyneth Paltrow a controversial Best Actress Oscar over favorites like Cate Blanchett (in Elizabeth) or Fernanda Montenegro (in Central Station).
Many awards season experts believe that the film won due to the tactics employed by producer Harvey Weinstein, as noted in a report from Vanity Fair.
'Green Book' wins Best Picture at the 2019 Oscars.
Viggo Mortensen and Mahershala Ali in 'Green Book.'
DreamWorks Pictures
The Green Book movie was based on a real person named Dr. Don Shirley — a pianist who toured the American South during segregation and continuously changed many of the details about his life.
This result was very upsetting to many cinema lovers. At the time Out argued that Green Book was the "white savior, feel-good movie of award season" and discussed its lack of exploration of Shirley's sexuality:
"It's unclear how Shirley himself identified on the sexuality spectrum. Unfortunately, we may never know. That is until someone actually makes the movie we all thought we were going to see."
'Bohemian Rhapsody' wins Best Editing at the 2019 Oscars.
Michael Keaton and John Ottman at the 2019 Academy Awards.
Kevin Winter/Getty Images
The controversies at the 91st Academy Awards were endless!
The Freddie Mercury biopic Bohemian Rhapsody was already controversial for even being nominated in the Best Picture category. Then, the film won Best Actor (for Rami Malek) despite its mishandling of Mercury's sexuality. The movie also won Best Film Editing (though many critics, including one from IndieWire, called it a "masterclass in bad editing").
Roman Polanski wins Best Director for 'The Pianist' at the 2003 Oscars.
Roman Polanski holding his Academy Award trophy for Best Director.
Pool BENAINOUS/LEFRANC/Gamma-Rapho via Getty Images
In 1978, director Roman Polanski fled the United States to avoid being jailed for unlawful sex with a 13-year-old girl, as reported by CBS News. Two decades later, the director was nominated at the Oscars for his film The Pianist, but didn't attend the ceremony due to his fear of being arrested.
Nonetheless, Polanski still won the Oscar for Best Director for The Pianist — subsequently receiving a standing ovation (via Newsweek).
Woody Allen wins Best Screenplay for 'Midnight in Paris' at the 2012 Oscars.
Official poster for 'Midnight in Paris.'
Woody Allen is one of the most controversial Oscar winners ever. In 1980, he was nominated for Best Screenplay for Manhattan — a film in which he plays a middle-aged man dating a high school girl.
More than a decade later, Allen started a sexual relationship with his ex-partner's 21-year-old daughter, Soon-Yi Previn, and was accused of sexually abusing his (then seven-year-old) daughter Dylan Farrow in 1992, as reported by BBC News. As the filmmaker continued to deny any wrongdoings, he won an Academy Award for Best Original Screenplay at the 2012 Oscars for Midnight in Paris.
Adrien Brody wins Best Actor for 'The Pianist' at the 2003 Oscars.
Adrien Brody at the 2003 Academy Awards.
Brian Vander Brug/Los Angeles Times via Getty Images
In 2003, Adrien Brody became the only person under the age of 30 to ever win a Best Actor Oscar for his performance in Roman Polanski's The Pianist. Not only was the young actor's win over veterans like Nicholas Cage, Michael Caine, Daniel Day-Lewis, and Jack Nicholson a surprise — but Brody went on to grab the presenter, Halle Berry.
The actor dipped her, and kissed her, in an action that has been looked down upon since the #MeToo movement, as reported by Variety.
Anthony Hopkins wins Best Actor over Chadwick Boseman at the 2021 Oscars.
Joaquin Phoenix presents Best Actor in a Leading Role category at the 2021 Oscars.
Todd Wawrychuk/A.M.P.A.S. via Getty Images
The 2021 Oscars were expected to end on a touching tribute to late actor Chadwick Boseman for Ma Rainey's Black Bottom — his final film before he passed from cancer at 43. Boseman was such a favorite that the Oscars producers rearranged the ceremony to have Best Actor as the final category instead of Best Picture, which meant that the night could end on an emotional high.
Instead, Anthony Hopkins, who wasn't present in the audience, won the award for The Father. The night ended with a very anticlimactic win.
Olivia Colman wins Best Actress over Glenn Close and Lady Gaga at the 2019 Oscars.
Olivia Colman; Glenn Close; Lady Gaga at the 2019 Academy Awards.
Frazer Harrison/Getty Images; VALERIE MACON/AFP via Getty Images; Kevin Winter/Getty Images
The entire 2019 awards season built up momentum between Glenn Close and Lady Gaga as to which of the two would win the Academy Award for Best Actress.
On one side was Close, nominated for The Wife, but whose entire career was deserving of an Oscar. On the other side was Lady Gaga, a new face to the world of cinema, who delivered a breakout performance in A Star is Born.
In the end, however, Olivia Colman won Best Actress for playing Queen Anne in The Favourite.
