Top 23 Awkward Award Show Moments of Each Year (2000 - 2022)

“20th BRIT Awards” (2000)

“58th Golden Globe Awards” (2001)

Elizabeth Taylor is the definition of a screen legend, making her more than qualified to present the Best Picture - Drama Golden Globe. Jeff Bridges gave Taylor the introduction she deserved, building her up as one of the all-time greats. Taylor received a standing ovation and then… well, for somebody who won so many awards during her lifetime, she seemingly forgot how award shows work. Prematurely opening the envelope, Taylor needed Dick Clark to come onstage and remind her to read the nominees first. Taylor proceeded to list off the nominees… very slowly with her words slurred, finally announcing “Gladiator” as the winner. Whether or not Taylor had been drinking as some have speculated, one thing’s for certain. Jinkx Monsoon does a dead-on impression of Liz!

“19th MTV Video Music Awards” (2002)

“75th Academy Awards” (2003)

With the Iraq War commencing just days earlier, political tensions were high going into the 2003 Oscars. Jack Nicholson reportedly suggested that the Best Actor nominees boycott the ceremony while director Hayao Miyazaki - who won Best Animated Feature that year - refused to attend. Michael Moore was in attendance, however. And when “Bowling for Columbine” won Best Documentary Feature, Moore gave the politically-charged speech his fans might expect. Yet, nothing could prepare the audience for Moore’s comments on George W. Bush, describing everything about his presidency as “fictitious.” The mix of boos and applause only made Moore’s speech more uncomfortable. Moore didn’t get to finish his speech at the Oscars, but he’d finally share the rest at the Critics’ Choice Documentary Awards almost 15 years later.

“61st Golden Globe Awards” (2004)

Michael Douglas has had a storied career, and you definitely felt its length when he received the Cecil B. DeMille Award. Danny DeVito and Sharon Stone spent nearly 10 minutes reminiscing about Douglas’ cinematic contributions, complete with drawn-out clips. This might be acceptable at the Governors Awards or the AFI Life Achievement Awards, but the Golden Globes are already lengthy enough with nearly two dozen other statutes to hand out. Then when Douglas’ tribute FINALLY wrapped up, it suddenly dawned on the audience that he still needed to give a speech. He did not keep it short. After nearly 20 minutes of squirming in their seats and checking their watches, the uncomfortable viewers breathed a sigh of relief as they cut to commercial.

“57th Primetime Emmy Awards” (2005)

Capitalizing on “American Idol,” the 2005 Emmy telecast had some of TV’s biggest stars sing popular theme songs. They kicked off “Emmy Idol” with Donald Trump - then best-known for “The Apprentice” - and Megan Mullally in character as Karen Walker. The song? The “Green Acres” theme with Donald trading his blue suit and red tie for farmer attire. Watching this cringey spectacle, we all thought the same thing: eleven years from now, that man is going to be elected president and “Will & Grace” will be revived shortly after. While Trump never won a competitive Emmy, he did share in this Emmy Idol win - which even Mullally regrets. Quite frankly, Kristen Bell should’ve won for her “Fame” rendition, but Trump is known for beating more qualified candidates.

“34th American Music Awards” (2006)

Other than a chair falling over, the Pussycat Dolls’ performance at the 2006 AMA Awards almost went off without a hitch. Then, with less than a minute left, Melody Thornton stormed onto the stage. If you forgot that this group had a sixth member, you definitely remembered as Thornton started singing off-pitch over Nicole Scherzinger. The performance left many feeling confused and probably pressed a few buttons. 14 years later, Thornton explained that a lost passport caused her to miss rehearsals, landing shortly before the show. So, if you thought Thornton’s “grand finale” looked unrehearsed, that’s because it was. Feeling “worthless” in the group, Thornton went solo a few years later and announced that she wasn’t taking part in the reunion.

“35th Annual American Music Awards” (2007)

“7th Annual Premios MTV Latinoamérica” (2008)

“26th MTV Video Music Awards” (2009)

Somehow, this makes Sacha Baron Cohen flying onto Eminem’s face feel restrained.

“27th MTV Video Music Awards” (2010)

When a dress is displayed in a museum and even gets a Wikipedia page, that must mean it’s either a revelation of fashion or a hand-scratching misfire. Where does the meat dress place? That kind of depends who you ask, but when Lady Gaga accepted Video of the Year in this raw flank steak ensemble, you could hear jaws across the globe hitting the floor. While Gaga was already famed for her elaborate fashion stunts, this was so out-there that a lot of people still don’t know what to think. Of course, vegans have their opinions. Gaga would explain that the dress is a statement about fighting for your rights. While the message is strong, it might’ve been overshadowed by this moment’s sheer absurdity.

“68th Golden Globe Awards” (2011)

“39th Annie Awards” (2012)

About five years before another envelope mixup, animation’s biggest night had a similar fiasco. Presenting Best Animated Television Production - Preschool, actress Brittany Snow announced the winner, “The Amazing World of Gumball.” Almost everyone quickly realized that something was amiss, seeing how “Gumball” wasn’t a nominee. “Gumball” actually won Best Animated Television Production – Children, which was supposed to be announced later. Host Patton Oswalt hurried onto the stage, explaining the situation with some well-timed one-liners and embracing the awkwardness of it all. Before having the “Gumball” crew come up and accept, Patton cracked a few more jokes at co-presenter Jason Marsden’s expense and assured Snow it was alright. We mean, it’s not like she was presenting Best Picture at the Academy Awards…

“20th Billboard Music Awards” (2013)

“86th Academy Awards” (2014)

“72nd Golden Globe Awards” (2015)

“73rd Golden Globe Awards” (2016)

Several years after the meat dress, Lady Gaga stunned in Versace at the Golden Globes. While it wasn’t her most eccentric outfit, Gaga inspired at least one head-turning look courtesy of Leonardo DiCaprio. As Gaga slid behind him on her way to the stage, DiCaprio’s laughter turned to surprise with a cringey expression. The moment went by so quickly that the average viewer might’ve missed it at first. If the internet is known for one thing, though, it’s turning a brief Leonardo DiCaprio gesture into a viral moment. Although some assumed he was throwing shade, DiCaprio explained that he didn’t know what was passing him. The two were reportedly seen laughing it up at the afterparty, although the GIF remains an awkward time capsule.

“89th Academy Awards” (2017)

“75th Golden Globe Awards” (2018)

“76th Golden Globe Awards” (2019)

Hollywood has made great strides for diversity in recent years with films like “Crazy Rich Asians.” However, that doesn’t undo the mistakes that the industry was still making only a few years earlier. Co-hosting the Golden Globes, Sandra Oh confronted the problematic casting of “Ghost in the Shell,” which enlisted Scarlett Johansson over an Asian lead, and “Aloha,” which starred Emma Stone as a captain who’s supposed to be part Chinese and Hawaiian. Stone was in attendance that night, having been nominated for “The Favourite.” Although the camera didn’t cut to her, Stone could be heard shouting, “I’m sorry,” in the distance. The joke itself is biting, but having Stone present elevated the moment to another level of hilarious awkwardness.

“77th Golden Globe Awards” (2020)

After a four-year absence, Ricky Gervais returned to host the Golden Globes for what he claimed would be his last time. As such, Gervais didn’t care who he offended - not that he ever cared that much to begin with. Gervais’ shots at Joe Pesci and Martin Scorsese’s height could be seen as nice compared to his jokes about the movie “Cats.” Gervais took no prisoners, and we’re not just talking about Felicity Huffman, Jeffrey Epstein, and Harvey Weinstein. He called out all of Hollywood for the lack of diversity, media giants taking over everything, and hypocritical celebrities using their acceptance speeches to push political agendas. Gervais received plenty of awkward looks, although Tom Hanks easily gave us the most meme-worthy reactions.

“93rd Academy Awards” (2021)

After Anthony Hopkins won Best Actor at the BAFTAs, it appeared the late Chadwick Boseman might not be the Oscar frontrunner. At this point, the Oscar producers should’ve reconsidered saving Best Actor for last. They stayed the course, however, hoping to end with a heartfelt speech from Boseman’s widow, Taylor Simone Ledward. Well, an absent Hopkins won. Whoever you think gave the better performance, abruptly ending on this note was uncomfortable for everybody, especially Boseman’s family and Hopkins - who subsequently recorded a speech. It’d be one thing if the Academy acknowledged that this was a misfire. Instead, co-producer Steven Soderbergh doubled down, saying, “If [Boseman] were to win and his widow were to speak on his behalf, there would be nowhere to go after that.”

“94th Academy Awards” (2022)

It was the slap heard round the world… except the censored parts. The 2022 Oscars took a turn after Chris Rock compared Jada Pinkett Smith’s shaved head to G.I. Jane. Since Pinkett Smith has alopecia, nobody would’ve blamed Will Smith if he called out Rock on social media. Instead, Smith literally took matters into his own hands, slapping Rock in front of 16 million viewers. Smith essentially confirmed that this wasn’t a bit as he angrily cursed Rock out. It was hard to move past this display, especially since Smith later won Best Actor, describing himself as a “vessel for love.” Smith has released an apology, but what should’ve been the pinnacle of his career will now be remembered for “one little fight.”