31 Most Awkward Oscar Moments of All Time

The 31 Most Cringe-Worthy Oscar Moments of All Time

(Image credit: Getty Images)

published 20 January 2020

Are you ready for the 92nd annual Academy Awards? It's all happening on February 9 and we're already assuming Once Upon a Time in Hollywood will snag a bunch of awards and expecting some iconic fashion looks. Ahead of the biggest night in Hollywood, we're taking a look back at some of the most uncomfortable moments we've ever had to watch through our television screens. You know, those moments where it's painful to watch but you can't quite bring yourself to look away. Here's to a 2020 Oscars where everyone keeps their clothes on.

1973: When Marlon Brando didn’t accept his award.

Brando won the Oscar for "Best Actor," but he wasn't there to accept—rather, he sent Sacheen Littlefeather, a Native American activist, to decline and protest his award. The audience wasn't thrilled, which made it even harder to watch.

1974: When a photographer streaked across the stage.

Just as host David Niven was introducing Elizabeth Taylor to present the award for "Best Picture," a naked man ran across the stage behind him. The man in question was photographer Robert Opel, who worked for the LGBTQ magazine, The Advocate. Niven was quick to say, "Isn't it fascinating to think that probably the only laugh that man will ever get in life is by stripping off and showing his shortcomings?"

3 of 31 1989: When Rob Lowe sang a duet with Snow White.

The entire 11-minute performance shows Disney princess Snow White attending the Oscars—and was incredibly weird for people to watch. What was even weirder was when actor Rob Lowe appeared on stage to sing a duet with the princess (skip to five minutes in). Lowe opened up to the New York Times about the debacle in 1992, saying, “Look, the academy asked me to take that role so I was a good soldier and did it. You can’t be your own manager and agent and soothsayer—you have to take risks. And on that one I got shot in the foot.”

1998: When James Cameron quoted his own movie in his acceptance speech.

Cameron had just won the award for "Best Director" for his movie Titanic, and during his acceptance speech, brought his own ship down (too soon?). At the end of his speech, he shouted "I'm king of the world"—a line from the movie—and people were less than pleased, calling him arrogant.

1999: When Roberto Benigni stood up on the theater seats.

The Italian actor and director was so excited that the movie Life is Beautiful won the Oscar for "Best Foreign Film," he walked on the backs of seats. People thought his reaction was a bit overdramatic.

2000: When the 'South Park' creators mimicked iconic red carpet looks while high

South Parker creators Trey Parker, Matt Stone, and Marc Shaiman showed up to the 2000 Oscars red carpet in...women's clothing, awkwardly mimicking Jennifer Lopez and Gwyneth Paltrow. They later admitted they were on acid at the time.

2000: When Angelina Jolie shared a kiss on the lips with her brother.

Joile's brother, James, attended the Oscars with her, and they showed they were closer than the average siblings. The two shared a kiss on the lips, and people felt it was incestuous. A family friend gave some insight on the scene. "The day she kissed Jamie at the Oscars, it was the first day [her mom] was treated for cancer. They left the hospital together and got ready together,” the source said in an interview.

2001: When Björk arrived in a swan dress and laid an egg on the red carpet.

People were stunned when Björk walked the red carpet in a frilly swan dress—and even more so when she strategically "laid" six ostrich eggs on the red carpet. The now infamous dress is honored in the Museum of Modern art.

2003: When Adrien Brody passionately kissed Halle Berry after winning and Oscar.

After announcing that Brody won "Best Actor" for his performance in The Pianist, Berry was swept off her feet when he came to accept. Brody passionately kissed her on live television...and before she had a chance to say no. In an interview, she said the kiss wasn't planned and the entire time she was thinking "“What the f*ck is happening?” (The discomfort was palpable).

2009: When Jennifer Aniston had to present an award right in front of Brad Pitt and Angelina Jolie.

Five years after their divorce, Aniston was forced to present an Oscar right in front of Pitt and his girlfriend at the time, Angelina Jolie—and she was noticeably uncomfortable (as were we) about the whole thing.

2011: When James Franco and Anne Hathaway hosted.

In reversed gender roles, Franco wore a satin pink gown and Hathaway wore a tuxedo to host the 2011 Oscars. Despite their attempted comedic act, people weren't impressed and even referred to it as "one of the worst Oscar telecasts in history." Many critics pointed out that Hathaway seemed to be trying too hard while Franco wasn't trying hard enough.

2012: When Sacha Baron Cohen threw ashes on Ryan Seacrest.

Cohen appeared in character as Admiral General Aladeen from his movie The Dictator on the red carpet during the 2012 Oscars, carrying a golden urn full of ashes. While interviewing with Ryan Seacrest, Cohen/Aladeen accidentally spilled the ashes all over Seacrest who was presumably upset about the ordeal.

2012: When Angelina Jolie couldn't stop showing off her leg.

After Jolie posed in her side-slit gown at the Oscars, people began photoshopping her right leg onto other images—ultimately leading to the notorious "Angie's right leg" meme. Jolie didn't comment at the time, but later went on to say, "I honestly didn't pay attention to it. I don't watch those TV shows and if I go online and see something about myself, I don't click on it. And the people I surround myself with don't really talk about that kind of stuff," she said. "I heard something, but I didn't pay any attention. It's as simple as being a woman picking a dress you like and having a night, and not really thinking about anything else."

2013: When Set Macfarlane sang about boobs.

Macfarlane really made the audience uncomfortable when he performed a musical number about all the women in Hollywood whose boobs we've seen. Please notice how upset some of the women look when the camera is on them. Gloria Allred responded to Macfarlane's song saying, "It's one thing to be topless and to have that in the context of the film for a purpose in a particular scene for a particular reason. It's another to take it out of context and just focus on women's breasts."

2013: When Jennifer Lawrence tripped going on stage...

On her way up to the stage to accept "Best Actress" for her role in Silver Lining's Playbook, Lawrence tripped on the stairs. After hanging her head for a second, she went on to give her speech and collect her Oscar.

2014: ...And again on the red carpet one year later.

Poor Lawrence fell at the Oscars, making that two years in a row she's fallen—but this time she nearly took someone else down with her.

2014: When John Travolta was weird with Scarlett Johansson.

Despite Johansson's captured reaction in this photo, the actress said Travolta's Oscar kisses were more than acceptable. "The image that is circulating is an unfortunate still-frame from a live-action encounter that was very sweet and totally welcome," Johansson said. "That still photo does not reflect what preceded and followed if you see the moment live."

2014: When John Travolta didn’t know how to say Idina Menzel’s name...

When he introduced the Frozen star in 2014, Travolta either didn’t know how to say Menzel’s name or he had some sort of bit planned. Either way, he pronounced her name as “Adele Dazeem” in a weird accent and people were confused.

2015: ...And when she got John Travolta back the next year.

The following year, Menzel got payback and jokingly pronounced Travolta's name "Glom Gazingo." He then proceeded to oddly touch her face a lot, making us feel slightly uncomfortable.

2015: When Sean Penn made a green card joke.

Penn really angered people when he announced the winner for "Best Picture," Birdman. Before he called the name, he joked "Who gave this son of a b**ch a green card?" referring to Mexican director Alejandro González Iñárritu—and people accused Penn of being "racist and offensive."

2015: When Neil Patrick Harris performed a magic trick on stage...

Harris pulled off the biggest magic trick while hosting the Oscars, locking his winner predictions in a briefcase inside a glass box—and his guesses were shockingly accurate. Derek DelGaudio, a writer for Harris' show said, “At the Oscars, anything the host says is perceived as a ‘bit’ or ‘gag’ and there is little expectation of sincerity or truth." He added, "So, it’s very difficult to create an astonishing moment of disbelief when they never believed you in the first place.”

2015: ...And when he stripped down into his underwear.

Harris fully committed to putting on an entertaining show, so much so that he stripped down into nothing but his underwear, socks, and shoes on stage. Turns out he was just doing a bit to pay tribute to the movie Birdman.

2015: When Dakota Johnson had an uncomfortable moment with her mother during a red carpet interview.

During her red carpet interview, Johnson and her mom Melanie Griffith had a tense moment when they revealed she'd never seen Fifty Shades of Grey. Johnson tried to say "maybe one day," but her mom said it would be too strange.

2016: When Sam Smith thought he was the first gay man to win an Oscar.

During his acceptance speech, Smith hinted that he might have been the first openly gay man to receive an Oscar—but he was wrong. According to The Hollywood Reporter, "Elton John, Dustin Lance Black, Howard Ashman, and Scott Rudin were all openly gay when they accepted their Oscars."

2017: When Jan Chapman’s picture was included in the “In Memoriam” slideshow, but was still alive.

That awkward moment when everyone thinks you're dead, but really people confused you for someone else—yeah, that's what happened to Jan Chapman. A photo of the Australian costume designer was mistakenly used to honor another costume designer, Janet Patterson during the "In Memoriam" portion of the evening. Chapman was rightfully "devastated" when she saw her photo.

2017: When Auli’i Cravalho got hit in the head during her performance.

While performing the song "How Far I'll Go," from Moana, Cravalho was nearly hit in the head with a flag by a background dancer. We might have been cringing, but the 16-year-old proved she can handle anything and kept singing.

2017: When Nicole Kidman clapped weird.

Kidman was caught on camera clapping—which doesn't sound strange because it's an awards show and people clap for other people. But she was criticized for the way she clapped, which Kidman later explained was in an effort not to damage the rings she was wearing.

2017: When Brie Larson didn't clap for Casey Affleck.

Larson presented Affleck with the award for "Best Actor," but she chose not to clap for him—and her muted reaction didn't go unnoticed. “I think that whatever it was that I did onstage kind of spoke for itself,” she told Vanity Fair. Affleck had recently been sued by two women for sexual harassment while filming the movie I'm Still Here.

2017: When Jimmy Kimmel brought a bunch of spectators into the show.

Kimmel hosted last year's Oscars, and during part of the show, he brought a bus full of tourists inside to meet celebrities. The bit went from slightly awkward, with the spectators not knowing what to do, to extremely weird, when Denzel Washington "married" two of the tourists (and Jennifer Aniston gave them her sunglasses as a wedding gift).

2017: When the wrong winner for “Best Picture” was announced.

When Faye Dunaway and Warren Beaty announced the wrong winner for "Best Picture," it was arguably one of the most awkward moments in Oscars history. After La La Land had been announced as the winner, it was revealed there was a mistake and Moonlight should have won. Dunaway opened up about the confusion two months later and said, "[Beatty] took the card out, and he didn’t say anything. He paused, he looked over me, off-stage, he looked around, and I finally said, ‘You’re impossible.’ I thought he was joking! A dramatic pause.”

2018: A Kiss Snub Felt Around The World

Coming off the super awkward La La Land mixup, the bar was pretty low at the 2018 Oscars. Things were pretty calm until Blade Runner 2049 won the award for Best Visual Effects. One of the winners' wives went in for a kiss and it was genuinely painful to watch. Skip ahead to the 1:40 mark to see it for yourself.

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