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The most memorable Oscar moments of the past 20 years
Christopher Polk/Getty Images

The most memorable Oscar moments of the past 20 years

Everyone loves a good movie, and every once in a while the ceremony that hands out the film industry's highest honors can be just as entertaining as any blockbuster. We remember the hilarious hosts, the dramatic and touching speeches and the occasional stunning upset of a category win, making for great water cooler talk the next day. Yet even more than that, we remember the jokes that fall flat on their faces, the musical numbers that could best be described as "ill-advised" and the stage-crashing shockers that we're still talking about to this day. It's the out-of-nowhere surprises that keep us tuning back in year after year.

So as Oscar celebrates his 92nd birthday, let's take a look back at some of the most memorable (and we do mean memorable in every sense of the word) Academy Award moments of the past 20 years.

 
1 of 27

A year without hosts (2019 - 91st Academy Awards)

A year without hosts (2019 - 91st Academy Awards)
Robert Deutsch-USA TODAY NETWORK (Via OlyDrop)

There were numerous small-scale controversies leading into the Oscars last year, ranging from the announcement (and later scrapping) of the condescending "Most Popular Film" category to the hiring (and then firing) of Kevin Hart as host following the unearthing of offensive tweets directed toward the LGBTQ+ community. So how could a broadcast so often defined by its hosts go on without one? Well, surprisingly smoothly it turns out. Although Tina Fey, Amy Poehler and Maya Rudolph opened the show with a litany of ace jokes (“We are not your hosts, but we are going to stand here a little too long so the people who get a USA Today tomorrow think we hosted,” Fey quipped), the quick jump between awards and performances and presenters meant there was no dead air, fewer awkward transitions and a show so enjoyable we almost didn't mind that "Green Book" won Best Picture.

 
2 of 27

Lady Gaga and Bradley Cooper perform "Shallow" (2019 - 91st Academy Awards)

Lady Gaga and Bradley Cooper perform "Shallow"  (2019 - 91st Academy Awards)
Credit: Robert Deutsch-USA TODAY NETWORK

In a segment reportedly directed by Bradley Cooper himself, the raw, one-shot take of Lady Gaga and Cooper performing their "A Star is Born" hit, "Shallow," was one of the most hyped parts of the evening — and against all the odds, the two stars absolutely pulled it off (capping off an evening where Gaga took home the Best Original Song statue for writing it). Nuzzled next to each other with soft glances and a remarkable sense of intimacy, their performance of "Shallow" would soon become instantly legendary.

 
3 of 27

Melissa McCarthy and Brian Tyree Henry present Best Costume Design (2019 - 91st Academy Awards)

Melissa McCarthy and Brian Tyree Henry present Best Costume Design (2019 - 91st Academy Awards)
Robert Deutsch-USA TODAY NETWORK (Via OlyDrop)

Although many wondered before the biggest night in Hollywood whether the show would thrive without hosts, all the usual segments, presenters and banter we've come to expect were still there, and no segment that evening was arguably funnier than when Melissa McCarthy and Brian Tyree Henry presented Best Costume Design while wearing their ridiculous outfits semi-inspired by that year's nominee "The Favourite." McCarthy's frock was especially decadent and comical, with her long train dotted with statues of woodland creatures all looking up to her. Between this and ace turns from John Mulaney and Awkwafina, the Oscars once again realized that sometimes comedy is best in small doses.

 
4 of 27

Frances McDormand seizes the moment (2018 - 90th Academy Awards)

Frances McDormand seizes the moment (2018 - 90th Academy Awards)
Robert Deutsch-USA TODAY NETWORK

During a year when powerful men were forced off their seemingly untouchable pedestals due to heinous, striking allegations spurred on by the #MeToo movement, a tamer-than-usual Oscars telecast had a moment when Frances McDormand accepted her second career Best Actress statuette for "Three Billboards Outside Ebbing, Missouri." "OK, so I'm hyperventilating a little bit. If I fall over, pick me up," she started, before changing tone: "'...cause I've got some things to say." She made the women in the room stand up and implored people to hear them out as they have stories that need financed, then left with just two words: "Inclusion Rider." It's the clause in any Hollywood contract that says a crew must be specifically diverse to retain the talent, and months after her speech, many studios grapple with a sudden spark of interest in the once-uncommon term

 
5 of 27

The Biggest Best Picture Flub of All Time (2017 - 89th Academy Awards)

The Biggest Best Picture Flub of All Time (2017 - 89th Academy Awards)
Kevin Winter/Getty Images

Remember the name Cheryl Boone Isaacs, as she tried really hard. She was president of the Academy of Motion Pictures Arts and Sciences, and under her tenure counteracted controversies like #OscarsSoWhite by trying to get a broader base into the voting ranks so that true diversity is represented at the Oscars. Yet all her careful work couldn't have prepared her for the 2017 ceremony in which the one backstage agent of accounting firm PricewaterhouseCoopers was too busy capturing selfies with the stars to notice that during the biggest moment of the night — Best Picture — Warren Beatty and Faye Dunaway walked onto the stage not with the Best Picture envelope but with the backup envelope for Best Actress. The winner for that already-announced award was Emma Stone, and when Beatty opened up the envelope, he was genuinely confused (wouldn't you be?). Faye said the first thing she saw on there: "La La Land," and after winning a bunch of awards including Best Director, it made sense it would also take Best Picture.

Yet part way through the staff's many acceptance speeches, "La La Land" producer Jordan Horowitz was pulled aside to be informed that, in fact, the wrong name was read: It was supposed to be the acclaimed indie drama "Moonlight." Horowitz broke the news and held up the envelope, and virtually no one could believe what was happening. The wrong Best Picture was called. The "Moonlight" crew did all it could to salvage the moment, but confusion reigned, Boone Isaacs stepped down, PricewaterhouseCoopers issued multiple apologies, and the single most controversial — and memorable — Oscars moment of all time was born.

 
6 of 27

Lady Gaga's "The Sound of Music" performance (2015 - 87th Academy Awards)

Lady Gaga's "The Sound of Music" performance (2015 - 87th Academy Awards)
Kevin Winter/Getty Images

In celebrating the 50th anniversary of "The Sound of Music," the Oscars decided to bring in Lady Gaga to give a new rendition of the musical's classic songs. While the pairing may seem odd on its surface, Gaga, unlike most of her pop-diva contemporaries, actually has singing chops, and in tackling the "Sound of Music" songbook she genuinely blew the roof off the Dolby Theater. Her pitch, tone and presentation were perfect, not necessarily imitating Julie Andrews' performance so much as she inhabited it. The standing ovation was immediate, and we couldn't help but wonder why more Oscar performances aren't as impactful as this.

 
7 of 27

"Adele Dazeem" (2014 - 86th Academy Awards)

"Adele Dazeem" (2014 - 86th Academy Awards)
ROBYN BECK/AFP/Getty Images

It was (arguably) one of the biggest songs of that year and certainly the biggest hit musical number Disney has had in a long time. "Frozen" Fever was a real thing, and although she won a Tony Award for her role on Broadway's "Wicked," it was the iconic "Let It Go" that shot Idina Menzel into the spotlight. Yet when John Travolta introduced her to do the Best Original Song performance (which it expectedly won shortly thereafter), he somehow flubbed her name beyond all recognition. "Idina Menzel" got transformed into "Adele Dazeem," and the ridicule would follow both Travolta and Menzel for months to come. She got revenge the following year by getting to introduce him as "Glom Gazingo," but the original moment will go down in the Mispronunciation Hall of Fame.

 
8 of 27

The Ellen selfie (2014 - 86th Academy Awards)

The Ellen selfie (2014 - 86th Academy Awards)
Ellen DeGeneres/Twitter via Getty Images

During a surprisingly casual moment of the show, host Ellen DeGeneres is walking up and down the aisles of the Oscars, making jokes and trying to get selfies. She tries to get the most retweets of all time by getting a selfie with Meryl Streep , but in surprisingly organic fashion, other celebrities join in, from Brad Pitt to Lupita Nyong'o to Bradley Cooper to Jennifer Lawrence. It did what she hoped it would and became the single most retweeted image of all time... at least until Wendy's guy showed up.

 
9 of 27

Jennifer Lawrence's infamous dress trip (2013 - 85th Academy Awards)

Jennifer Lawrence's infamous dress trip (2013 - 85th Academy Awards)
Kevin Winter/Getty Images

Back when the world was still in its honeymoon phase with Jennifer Lawrence, she could seemingly do no wrong. In fact, when going up to the stage to accept her Best Actress award for "Silver Linings Playbook," her long, flowing dress caused her to trip on the stairs. Presenter Jean Dujardin started moving over to help before Lawrence picked herself up. Her first words at the mic? "You guys are just standing up 'cause you feel bad that I fell and that's really embarrassing, but thank you." Humble, humorous and real.

 
10 of 27

"We Saw Your Boobs" (2013 - 85th Academy Awards)

"We Saw Your Boobs" (2013 - 85th Academy Awards)
Kevin Winter/Getty Images

In a year where the Oscar broadcast was filled with many memorable moments — from Ben Affleck's impassioned speech upon winning Best Picture to the surprise tie in the Sound Editing category — nothing garnered more controversy than host Seth MacFarlane's opening number. In a piece that celebrated movies in which female actresses disrobed, many found the frat boy humor in bad taste, especially when considering some of the actresses mentioned were naked in scenes due to portrayals of sexual violence. The Academy has done a great job of preserving its history and putting virtually every acceptance speech and opening monologue on its YouTube channel for viewing en masse. Conspicuously, "We Saw Your Boobs" is absent.

 
11 of 27

Melissa Leo drops the F-bomb (2011 - 83rd Academy Awards)

Melissa Leo drops the F-bomb (2011 - 83rd Academy Awards)
Kevin Winter/Getty Images

Throughout the history of the televised Academy Awards up until 2011, the F-bomb had yet to have been dropped. Yet Melissa Leo, after having some fun banter with presenter Kirk Douglas, seemed awestruck by the sheer size of the room and the audience. Taking it all in, she said "When I watched Kate [Winslet win] two years ago, it looked so f---ing easy!" She then covered up her mouth, realizing what she did, and she just powered through like the pro that she is. Hey, it had to happen eventually.

 
12 of 27

James Franco and Anne Hathaway's hosting gig (2011 - 83rd Academy Awards)

James Franco and Anne Hathaway's hosting gig (2011 -  83rd Academy Awards)
Robert Gauthier/Los Angeles Times via Getty Images

Where to begin? While Anne Hathaway genuinely impressed with her singing chops during a cameo appearance in Hugh Jackman's spirited opening number in 2009, it kind of made sense for her to maybe be an Oscar host. But pairing her with James Franco put everything in a weird place. She tried giving it her all while he sleepwalked through his line reads, showed up in drag (which he claims was on the producer's insistence, which is why he looked so enthused doing it) and was universally hounded for not appearing to show up for one of the biggest television events of the year.

 
13 of 27

When the Documentary Short Subject winner was stage-crashed (2010 - 82nd Academy Awards)

When the Documentary Short Subject winner was stage-crashed (2010 - 82nd Academy Awards)
Michael Caulfield/WireImage/Getty Images

While there is a cult audience for the Short Film categories, the genre rarely is a subject of much note during the Academy Awards, save for padding your Oscars pool. Yet when the lovely Documentary Short Subject winner "Music by Prudence" was announced, director Roger Ross Williams took to the stage to talk about going to Zimbabwe and meeting Prudence, who was the lead singer in a band comprised of disabled musicians in one of Africa's poorest countries. However, the producer of the project, Elinor Burkett, interrupted Williams to say "Just like a man, never lets a woman talk. Isn't that just the classic thing?" The two had been feuding about the direction of the film and although both were winners, this public spat made headlines for all the wrong reasons and earns an otherwise lovely film a dubious spot in Oscar history.

 
14 of 27

Hugh Jackman's stellar opening number (2009 - 81st Academy Awards)

Hugh Jackman's stellar opening number (2009 - 81st Academy Awards)
Kevin Winter/Getty Images

We all knew that Hugh Jackman was a man of many talents, but the "Australia" star's musical theater background allowed him to deliver an opening number full of effortless one-liners ("Everything is being downsized because of the recession: next year I'll be starring in a movie called 'New Zealand'") and big Broadway-style belting, and he helped launch Anne Hathaway's singing career. It was whimsical and wonderful, but for our money, the best part was when Jackman did techno-inspired interpretive dancing to represent the film "The Reader," with Jackman cracking himself up by admitting he hadn't seen it. For such a tightly controlled broadcast, that little bit of lunacy went a long way and is now considered one of the best opening numbers, hands down.

 
15 of 27

Heath Ledger wins Best Supporting Actor posthumously (2009 - 81st Academy Awards)

Heath Ledger wins Best Supporting Actor posthumously (2009 - 81st Academy Awards)
Kevin Winter/Getty Images

While the gimmick of having previous Oscar-winning actors in a category come out and lavish praise upon the individual nominees grew real tired real fast, we endured it to get through just about the surest bet there was heading into the evening: the late Heath Ledger receiving a statue for his game-changing, instantly iconic performance as The Joker in Christopher Nolan's "The Dark Knight." Ledger's family accepted the award on his behalf, reading a simple and gorgeous written statement as everyone looked on in reverence. It was a sweet and authentic moment in a broadcast that is often completely devoid of them.

 
16 of 27

Comedians at the Oscars (2007 - 79th Academy Awards)

Comedians at the Oscars (2007 - 79th Academy Awards)
Michael Caulfield/WireImage/Getty Images

Three years after Jack Black and Will Ferrell earned well-deserved kudos for their "Get Off the Stage" routine at the 2004 ceremony, they somewhat rehash their bit in 2007 with the much longer, less-funny " Comedians at the Oscars." It's still amusing — just less impactful — even though Ferrell and Black still throw themselves into the absurdity of it all. Then John C. Reilly shows who the real singing comedian is, and it gets us all nostalgic for the "Walk Hard: The Dewey Cox Story" Best Original Song nomination that never was.

 
17 of 27

"It's Hard Out Here for a Pimp" wins the Oscar (2006 - 78th Academy Awards)

"It's Hard Out Here for a Pimp" wins the Oscar (2006 - 78th Academy Awards)
Steve Granitz/WireImage/Getty Images

All we're gonna say is that members of Three 6 Mafia were the only people to give a shout-out to Jesus that night.

 
18 of 27

Chris Rock takes a poll (2005 - 77th Academy Awards)

Chris Rock takes a poll (2005 - 77th Academy Awards)
M. Caulfield/WireImage/Getty Images

For both times that Chris Rock hosted, he has caused a stir, bringing an outsider perspective into what is ordinarily a self-congratulatory affair. While some criticized his monologue, his most revealing segment was when he went with a camera crew to the Magic Cinemas in L.A. to ask filmgoers what their favorite movie of the past year was. The answers ranged from "Alien vs. Predator" to "Saw" to "Chronicles of Riddick," and when he asks the attendees if they've seen nominated films like "Sideways" or "Finding Neverland," the participants give a resounding chorus of nos. It was rather subversive but also a reminder to the Academy that while it nominates films every single year, an Academy Award means little to some cinema goers: They're just going to the movies to have a good time.

 
19 of 27

Queen Bey slaying the Best Original Song nominees (2005 - 77th Academy Awards)

Queen Bey slaying the Best Original Song nominees (2005 - 77th Academy Awards)
Kevin Winter/Getty Images

There was no shortage of interesting Best Original Song nominees at the 2005 ceremony, but what was perhaps most striking is how after making a spectacular start to her solo career some two years prior, Beyoncé was absolutely everywhere during the broadcast for no discernible reason. No one was complaining though, as she sang the nominated song ("Look to your Path") from the foreign film "The Chorus" and the new number "Learn to Be Lonely" from "The Phantom of the Opera," and she duetted with Josh Groban on "Believe" from "The Polar Express" soundtrack. Nothing against the Counting Crows' "Accidentally in Love" or Antonio Banderas and Carlos Santana's rendition of "Al otro lado del rio" from eventual winner "The Motorcycle Diaries," but the night truly belonged to Beyoncé — we were all just lucky to be there.

 
20 of 27

Jack Black and Will Ferrell Sing "Get Off the Stage" (2004 - 76th Academy Awards)

Jack Black and Will Ferrell Sing "Get Off the Stage" (2004 - 76th Academy Awards)
M. Caulfield/WireImage/Getty Images

In the long history of the Oscars, it's fair to say that your comic bit probably isn't going to work unless your name is Bob Hope. However, Jack Black and Will Ferrell adding lyrics to the song that is played over rambling acceptance speeches was an inspired bit of comedy. They told everyone that when it comes to thanking your parakeet — you're boring. There were references to Del Taco for no reason. It was over before you knew it, leaving the audience wanting more. Up-and-down the spectrum, this is acknowledged as one of the funniest Oscar gags to date, mainly because it was short, sweet and didn't overplay its hand. Not boring.

 
21 of 27

Jim Carrey's presentation of Blake Edwards' honorary Oscar (2004 - 76th Academy Awards)

Jim Carrey's presentation of Blake Edwards' honorary Oscar (2004 - 76th Academy Awards)
M. Caulfield/WireImage/Getty Images

While no one will deny Blake Edwards' status as a cinematic legend, Jim Carrey's introduction to him — complete with a Cato impression — was nothing short of awkward. What turned things around, however, was a wheelchair-bound Edwards, excited to receive his award, but soon helpless as his wheelchair rocketed across the stage and crashed into a wall. Only then did the audience realize it was a physical comedy bit, but for the man who brought "The Pink Panther" movies to life, his larger-than-life comic routine showed us that when it comes to slapstick, you can't argue with the greats who came before us.

 
22 of 27

Barbra Streisand reading out the name "Eminem" (2003 - 75th Academy Awards)

Barbra Streisand reading out the name "Eminem" (2003 - 75th Academy Awards)
Frank Micelotta/Getty Images

Things started off noble enough: The ever-political Streisand introduced the Best Original Song category by talking about how she's "proud to live in a country that guarantees every citizen, including artists, the right to sing and to say what we believe." It was a sweet sentiment, but then came the moment that everyone was expecting: Streisand reading out Eminem's name . She gave it a nice "woo" beforehand, but it was a memorable generational clash. It's a shame Eminem wasn't there in person to pick up his award though; his fellow co-writer Luis Resto was fortunately on hand to accept the golden statue. 

 
23 of 27

Michael Moore's controversial "Bowling for Columbine" acceptance speech (2003 - 75th Academy Awards)

Michael Moore's controversial "Bowling for Columbine" acceptance speech (2003 - 75th Academy Awards)
Brian Vander Brug/Los Angeles Times via Getty Images

Michael Moore was no stranger to controversy, and upon winning the Best Documentary Feature statue for his audience-friendly gun control documentary, "Bowling for Columbine," he started things out by bringing all of his fellow nominees onstage, which was a kind gesture. Then he talked about how his fellow nominees liked "non-fiction," but we live in "fictitious times with fictitious election results that elects a fictitious president." While Moore kept going, so did the boos, and Moore was basically shouting against a wave of them by the time he was done. There have been controversial acceptance speeches before but never with as strong a reaction as this.

 
24 of 27

The Adrien Brody/Halle Berry kiss (2003 - 75th Academy Awards)

The Adrien Brody/Halle Berry kiss (2003 - 75th Academy Awards)
TIMOTHY A. CLARY/AFP/Getty Images

In a category stacked with former winners, Brody was the only new kid in town. Overcome with elation upon hearing his name called, he took the stage, shocked and overjoyed, and gave presenter Halle Berry a big smooch. As time moved on, the moment has gone from amusing to polarizing (he joked that he was "under a restraining order" when presenting Best Actress the following year), but its pop culture impact was undeniable, capping off one of the most memorable Oscar broadcasts of all time.

 
25 of 27

Whoopi's shimmering "Moulin Rouge" entrance (2002 - 74th Academy Awards)

Whoopi's shimmering "Moulin Rouge" entrance (2002 - 74th Academy Awards)
Ken Hively/Los Angeles Times via Getty Images

Whoopi Goldberg started her fourth hosting gig in spectacular fashion: coming down from the ceiling of the Kodak Theatre in full "Moulin Rouge"-inspired regalia. She says "Come and get me, boys!" a bunch of times (maybe a bit too many, but she was filling time as she descended), and some may have called her outfit a pale imitation of her "African Queen" outfit from the 1999 ceremony. But it was still the most talked about moment of an otherwise rather dull broadcast.

 
26 of 27

The swan dress (2001 - 73rd Academy Awards)

The swan dress (2001 - 73rd Academy Awards)
LUCY NICHOLSON/AFP/Getty Images

Although legend has spread about how utterly difficult the shooting of the ultra-depressing Lars von Trier musical "Dancer in the Dark" was, Björk came out of it with a whole new audience, from praise for her understated and heart-rending performance to the incredible soundtrack she made for the film. The nominated song "I've Seen It All" isn't an easygoing pop treat, which made its nomination all the more remarkable. Yet with that aside, all anyone could talk about was the swan-styled dress she wore during it, launching an endless parade of imitations but nonetheless endearing her to the mainstream for a brief, distinct moment.

 
27 of 27

Robin Williams performs "Blame Canada" (2000 - 72nd Academy Awards)

Robin Williams performs "Blame Canada" (2000 - 72nd Academy Awards)
TIMOTHY A. CLARY/AFP/Getty Images

In a year when the Oscar producers were on edge due to the fact that 55 Oscar statuettes were stolen just two weeks before (and that they had to print 4,200 replacement ballots due to a wrong postal routing station being listed), perhaps they didn't have time to sweat over the fact that a popular cartoon had an original, swear-laden comedy song from its R-rated movie spinoff get nominated in the Best Original Song category. Some were worried, but hiring a performer as cartoonish as Robin Williams seemed like a safe bet. And while he did give it some oomph (and carefully covered up the swear words with gasps from the chorus), Williams was a seasoned vet who knew which lines he could and could not cross, so he had fun while running a tight-if-straightforward performance. Nonetheless, after years and years of placid Best Original Song performances, this was one that will be remembered as distinct, unique and truly inimitable.

Evan Sawdey is the Interviews Editor at PopMatters and is the host of The Chartographers, a music-ranking podcast for pop music nerds. He lives in Chicago with his wonderful husband and can be found on Twitter at @SawdEye.

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