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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 awhile, the ceremony which 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 face, 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 90th 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 26

Jack Nicholson's too suave acceptance speech (1998 - 70th Academy Awards)

Jack Nicholson's too suave acceptance speech (1998 - 70th Academy Awards)
TIMOTHY A. CLARY/AFP/Getty Images

There goes ol' Jack. For a man who is known for his intense screen presence, his acceptance speeches, across the board, have been points of great joy, and his win for "As Good As It Gets" was no exception. From wearing his trademark sunglasses in the audience to literally dancing and skipping his way to accept the award, his speech had tailor-made jokes about Matt Damon's youth and long-running Oscar producer Gil Cates "sweating" backstage due to how long he was taking. "I'd like to thank everyone tonight for looking so good," he said, but by the time he walked off stage, Nicholson looked like how he often looked: like a winner.

 
2 of 26

The greatest acceptance speech(es) of all time? (1999 - 71st Academy Awards)

The greatest acceptance speech(es) of all time? (1999 - 71st Academy Awards)
TIMOTHY A. CLARY/AFP/Getty Images

Is this the most iconic acceptance speech of all time? Well, if anything, it's certainly the most memorable journey a winner has taken to get up to the Oscar stage. Even before Sophia Loren managed to open up the envelope to announce Roberto Benigni as the winner of the Best Foreign Film Academy Award, the crowd was chanting out "Roberto!" When he won, she waved the envelope in the air, and a clearly-overjoyed Benigni began walking over chairs in the audience to claim his prize. When he won again for Best Actor later in the evening, he ended up walking to the stage this time, but still overwhelmed with his clear, palpable joy. "This is a terrible mistake – as I've used up all my English!" Then he makes references to Jupiter and laying down with everyone in the firmament. Whether you love or hate the film, these speeches will last through the ages.

 
3 of 26

The weirdest Best Original Score presentation you've ever seen (1999 - 71st Academy Awards)

The weirdest Best Original Score presentation you've ever seen (1999 - 71st Academy Awards)
Ron Galella, Ltd./WireImage/Getty Images

Back in the day, the Best Original Score award was actually split in two, with a separate Oscar given for both "Musical/Comedy" and "Dramatic." After Stephen Warbeck won the Musical/Comedy gong for "Shakespeare in Love," something odd happened. Geena Davis introduced five dancers that took center stage and gave dramatic interpretations of the nominated scores. Because, when you think "Pleasantville," why wouldn't you think of a dude in dance pants, bare chest, and an unbuttoned jacket doing leaping pirouettes? It wasn't the most awkward thing we've seen at the Oscars in the past two decades, but it runs pretty darn close.

 
4 of 26

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

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

In a year where 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. While some were worried, 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 is 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.

 
5 of 26

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 those praising 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 easy-going pop treat, which makes its nomination all the more remarkable. Yet all 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.

 
6 of 26

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 regalia from the 1999 ceremony, but it was still the most talked about moment of an otherwise rather dull broadcast.

 
7 of 26

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, and 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 went 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.

 
8 of 26

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 nice and 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, the boos were immediate, 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.

 
9 of 26

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. 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. 

 
10 of 26

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, soon helpless as his wheelchair rocketed off 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 that came before us.

 
11 of 26

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 they play off rambling acceptance speeches to 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.

 
12 of 26

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," the new number "Learn to Be Lonely" from "The Phantom of the Opera," and duetted with Josh Groban on the number "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.

 
13 of 26

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 no's. It was rather subversive, but also a reminder to the Academy that while you nominate 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.

 
14 of 26

"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 Three 6 Mafia were the only people to give a shout-out to Jesus that night.

 
15 of 26

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 comes in to show who the real singing comedian is, and it just gets us all nostalgic for the "Walk Hard: The Dewey Cox Story" Best Original Song nomination that never was.

 
16 of 26

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.

 
17 of 26

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'"), big Broadway-style belting, and 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 hasn't seen "The Reader." 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.

 
18 of 26

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, they rarely are 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 getting to meet Prudence, leading a band that was filled with 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 a film a dubious spot in Oscar history.

 
19 of 26

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 just 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.

 
20 of 26

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 inside it. 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 just powered through like the pro that she is. Hey, it had to happen eventually.

 
21 of 26

"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 musical number that celebrates movies where female actresses disrobed, many found the fratboy 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 their history and putting virtually every acceptance speech and opening monologue on their YouTube channel for viewing en masse. Conspicuously, "We Saw Your Boobs" is absent.

 
22 of 26

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 the stage to accept her Best Actress award for "Silver Linings Playbook," her long, flowing dress caused her to trip on the award stairs leading up to the podium. 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 'cos you feel bad that I fell and that's really embarrassing, but thank you." Humble, humorous, and real.

 
23 of 26

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 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.

 
24 of 26

"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 presented 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 Gozingo," but the original moment will go down in the Mispronunciation Hall of Fame.

 
25 of 26

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 of 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.

 
26 of 26

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 the President of the Academy of Motion Pictures Arts and Sciences, and under her tenure counteracted controversies like #OscarsSoWhite by trying to get a broader and more diverse base into the voting ranks so that true diversity is represented at the Oscars. Yet all her careful preparation 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, held up the envelope, and virtually no one could believe what was happening. The wrong Best Picture was called. The "Moonlight" crew did all they could to salvage the moment, but confusion reigned, Cheryl Boone Isaacs stepped down, PricewaterhouseCoopers issued multiple apologies, and the single most controversial – and memorable – Oscars moment of all time was born.

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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