Top 20 Unforgettable Moments in Oscars History

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Ignacio Weil

Entertainment - January 28th 2025, 02:00 GMT+1

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In this list, we’re diving into the most famous Oscars moments that live rent-free in our heads – whether they were moving and groundbreaking for the industry, or so cringe-worthy they keep us awake at night.

Think we missed an iconic Oscars moment? Well, why not drop it in the comments and let us know? We’re all ears!

Cropped Natalie Portmans cape protest — 20. Natalie Portman’s Fashion Statement with a Message (2020)

Natalie Portman wasn’t just serving looks; she was serving *justice*. Draped in a black Dior cape embroidered with the names of female directors snubbed that year, Portman’s red carpet stroll turned into a mic-drop moment for gender equality. “Oh, this old thing?” she probably didn’t say, as the names of Greta Gerwig, Lulu Wang, and others subtly shimmered in gold thread. Some called it “quiet activism,” but let’s face it: nothing about making a statement at Hollywood’s biggest night is quiet. Did it fix the problem? No. But did it make Twitter collectively gasp? Absolutely. Natalie proved that fashion can be a protest, and we’ll never look at embroidery the same way again.

Cropped Eminems surprise performance — 19. Mom’s Spaghetti: Eminem Crashes the Oscars (2020)

Lose yourself? More like, lose your mind. Nearly two decades after winning an Oscar for *Lose Yourself –* and famously skipping the ceremony to, uh, nap – Eminem stormed the stage like it was 2002 all over again. The audience reaction was the real star, though: some were bopping along (looking at you, Idina Menzel), while others were visibly confused, likely thinking, “Wait, why is *this* happening now?” Regardless, Marshall Mathers didn’t miss a beat, reminding us all that his palms might still be sweaty, but his lyrics are timeless. It was random, nostalgic, and exactly the kind of chaotic energy we didn’t know we needed.

Cropped Whoopi Goldberg hosts in costume — 18. Whoopi Goldberg is a Queen (Literally) (1999)

Whoopi Goldberg hosting the Oscars is a vibe. Whoopi Goldberg hosting the Oscars in full costume changes? Iconic. For the 1999 ceremony, she pulled out all the stops, from a sparkly showgirl ensemble to a regal Elizabethan gown that could’ve doubled as a museum exhibit. Each costume screamed, “This is my stage, and I’ll wear what I want!” Sure, the Oscars are about honoring cinema, but Whoopi made it about having fun, reminding everyone that even the most buttoned-up event in Hollywood could use a little camp. Her hosting style didn’t just break the mold; it blew it up in glitter and sequins.

Cropped Adrien Brody kisses Halle Berry — 17. Adrien Brody Seals the Deal with a Smooch (2003)

What do you do when you win an Oscar for *The Pianist*? Apparently, you plant a big, unscripted kiss on Halle Berry, who looked as stunned as the rest of us. Adrien Brody’s win was historic – he was the youngest-ever Best Actor winner – but his impromptu lip-lock made headlines even faster. Was it charming? Awkward? Maybe both? To his credit, Halle played along like a pro, but the moment remains divisive. Love it or cringe at it, it’s hard to forget. Brody may have walked away with an Oscar, but it’s the smooch that got people talking.

Cropped Jennifer Lawrence trips — 16. Jennifer Lawrence’s Red Carpet Acrobatics (2013)

Ah, the moment Jennifer Lawrence cemented her status as Hollywood’s most relatable star. Walking up to accept her Best Actress Oscar for *Silver Linings Playbook*, she tripped on her Dior gown in front of millions. Most people would’ve melted into a puddle of embarrassment, but J-Law? She turned it into a moment of self-deprecating charm, quipping, “You guys are just standing up because you feel bad that I fell.” The stumble didn’t overshadow her win – it *enhanced* it. Suddenly, the girl-next-door vibes she was known for felt even more real, and we all fell in love with her a little harder.

Cropped Marlon Brando rejects Oscar — 15. The Oscar Marlon Brando Said “No Thanks” To (1973)

Hollywood is no stranger to drama, but when Marlon Brando sent Sacheen Littlefeather to reject his Best Actor Oscar for *The Godfather*, jaws hit the floor. Brando used the moment to protest the mistreatment of Native Americans in film, and Littlefeather, dressed in traditional Apache attire, delivered a poised, powerful speech that was met with both applause and boos. It was bold, controversial, and way ahead of its time. Brando’s absence left the Academy scrambling, and while the move was divisive, it sparked conversations about representation in an era when no one wanted to have them. Also, imagine how wild Twitter would’ve been if it had existed back then – absolute chaos.

Cropped Angelina Jolie and her brother — 14. Angelina Jolie’s Family Affair (2000)

Angelina Jolie didn’t just win the Best Supporting Actress Oscar for *Girl, Interrupted –* she won a lifetime of awkward headlines. When she kissed her brother, James Haven, on the lips and declared, “I’m so in love with my brother right now,” the world collectively did a double take. Sure, it was probably just an innocent display of sibling affection, but Hollywood doesn’t exactly do subtle. The tabloids had a field day, and the moment lives on as one of the most cringe-worthy yet oddly fascinating footnotes in Oscars history. Angelina’s speech might have been heartfelt, but let’s be real – it’s the kiss everyone remembers.

Cropped Glenn Close dances to Da Butt — 13. Glenn Close Steals the Show with a Booty Shake (2021)

The 2021 Oscars were a bit… weird, and Glenn Close dancing to “Da Butt” somehow managed to be both the highlight and the most cringe-inducing moment of the night. During a trivia game segment that no one really asked for, Close not only shocked everyone by correctly identifying the 1988 funk classic, but she took it one step further – literally – and got up to shake what her mama gave her. Was it funny? Absolutely. Was it also a little uncomfortable to watch one of Hollywood’s most revered actresses twerk in a setting that screamed “overly scripted spontaneity”? Oh, 100%. Bless Glenn for fully committing, but let’s be real: the secondhand embarrassment was palpable. If the Oscars were aiming for “internet gold,” they got it… just not for the reasons they might’ve hoped.

Cropped Nicole Kidmans clap — 12. Nicole Kidman’s Seal of Approval (2017)

Leave it to Nicole Kidman to turn clapping into a viral sensation. At the 2017 Oscars, cameras caught her delivering what can only be described as a “seal-like” clap, her fingers splayed wide apart like she was trying to avoid smudging wet nail polish. Social media lost its collective mind, with theories ranging from borrowed jewelry to avant-garde technique. Kidman later explained she was trying not to damage a massive diamond ring, but by then, the moment had already entered the meme hall of fame. Who knew applause could be so entertaining? Honestly, we should all aspire to clap with that level of drama.

Cropped Sam Smiths speech blunder — 11. Sam Smith’s Awkward Oscars Fact Check (2016)

Sam Smith took home an Oscar for Best Original Song (*“Writing’s on the Wall”* from *Spectre*), but what he *didn’t* take home was a fact-checker. During his acceptance speech, Smith incorrectly claimed he might be the first openly gay man to win an Oscar, sparking confusion, debate, and a collective “Huh?” from the audience. (Spoiler alert: He wasn’t.) The internet quickly pointed out icons like Elton John had already paved the way. Sam later admitted he misspoke, but the damage – or entertainment, depending on your perspective – was done. It’s a classic case of “Oops,” and proof that sometimes, less is more when it comes to speeches.

Cropped John Travolta mispronounces Idina Menzel — 10. John Travolta Introduces “Adele Dazeem” (2014)

If there were an Oscar for Most Bizarre Introduction, John Travolta would win it hands down. In 2014, while introducing Idina Menzel to perform *Let It Go* from *Frozen*, Travolta inexplicably called her… Adele Dazeem. Yes, *Adele Dazeem*. The flub sent the internet into a frenzy, with memes and mockery spreading faster than Elsa’s ice magic. The best part? Travolta delivered the line with such confidence that you almost believed *Adele Dazeem* was a real person. To her credit, Idina Menzel crushed her performance, but this moment? It’s all Travolta. Years later, it’s still the gift that keeps on giving, and we’re forever grateful for the glorious absurdity of it all.

Cropped The streaker incident — 9. When the Oscars Got Streaky (1974)

The 1974 Oscars gave us one of the most hilariously shocking moments in its history – a streaker casually running across the stage in the middle of the ceremony. As David Niven was introducing Elizabeth Taylor, the streaker, wearing nothing but a smile, dashed behind him, flashing the audience in more ways than one. Without missing a beat, Niven quipped, “Isn’t it fascinating to think that probably the only laugh that man will ever get in his life is by stripping off and showing his shortcomings?” The crowd roared, and Niven’s legendary comeback made the incident even more iconic. It’s proof that even streaking can be elevated by a bit of British wit.

Cropped Parasite sweeps — 8. Parasite Cleans House (2020)

When *Parasite* made history at the 2020 Oscars, it felt like a win for everyone. Bong Joon-ho’s masterpiece didn’t just take home the award for Best International Feature – it became the first non-English-language film ever to win Best Picture. Oh, and it snagged Best Director and Best Original Screenplay, too, because why not go all out? The audience erupted in cheers, and Bong himself charmed everyone with his humble, hilarious speeches (and his open adoration for his Oscar trophies, which he said would drink together). The night was an electric celebration of global cinema, and let’s face it, it was way more exciting than the usual predictable wins. Parasite’s victory? Pure, unadulterated *chef’s kiss*.

Cropped Lady Gaga and Bradley Coopers Shallow — 7. Gaga, Cooper, and the Chemistry We Can’t Forget (2019)

When Lady Gaga and Bradley Cooper performed *Shallow* at the 2019 Oscars, it felt like the room collectively held its breath – and maybe sent a cheeky text asking, “Wait, are they *together*?” The chemistry between them was so intense, it practically radiated off the stage. Gaga’s powerhouse vocals, Cooper’s soulful gaze, and that intimate piano moment had everyone feeling *some type of way*. It was captivating, emotional, and yes, a little cringe when you remembered Cooper’s girlfriend was sitting right there. The internet went wild with speculation, but the duo kept insisting it was all *acting*. Sure, Jan. Either way, this performance lives rent-free in all our minds.

Cropped Roberto Benigni celebration — 6. Roberto Benigni Jumps for Joy (Literally) (1998)

When Roberto Benigni won Best Actor for *Life is Beautiful*, he turned the Oscars into a full-on party. Leaping out of his seat, he climbed over chairs (and probably a few startled celebrities) to reach the stage, arms flailing and joy radiating from every pore. By the time he got to the microphone, the audience was already on their feet, clapping and laughing. His acceptance speech was as chaotic and delightful as his entrance, delivered with broken English and unfiltered excitement. It was a moment of pure, unpolished glee – a refreshing reminder that sometimes, the Oscars aren’t about cool composure but about celebrating like your life just got a little more beautiful.

Cropped Heath Ledgers posthumous win — 5. Heath Ledger’s Legacy Shines Bright (2009)

When Heath Ledger was awarded Best Supporting Actor for his chilling, transformative performance as the Joker in *The Dark Knight*, it was more than just a win – it was a tribute. The room was somber as his family accepted the Oscar on his behalf, with many visibly emotional. Ledger’s performance had redefined the superhero genre and turned a comic book villain into a terrifyingly human force of chaos. His posthumous win marked only the second time an actor had received the honor, and it served as a bittersweet reminder of his immense talent and tragic passing. It wasn’t just an Oscar moment; it was a collective nod to a star taken far too soon.

Cropped Leonardo Di Caprio finally wins — 4. Leo Finally Gets His Golden Ticket (2016)

After years of memes, internet pleas, and the general feeling that the Academy was trolling him, Leonardo DiCaprio finally snagged the elusive Oscar for *The Revenant*. The moment he walked onstage, you could feel the world exhale. Fans had spent years obsessing over his near-misses, so when his name was finally called, it felt like a personal victory for everyone. True to form, Leo used his speech to spotlight climate change, proving he’s a class act even while basking in long-overdue glory. It was the ultimate "patience pays off" moment and a rare time when the Oscars felt like justice was served.

Cropped Moonlight and La La Land mix up — 3. And the Oscar Goes to… Wait, What?! (2017)

The Oscars are known for drama, but no one expected *this*. When Faye Dunaway and Warren Beatty announced *La La Land* as the Best Picture winner, the cast and crew rushed the stage to celebrate. The only problem? It wasn’t true. In what will forever be remembered as the greatest live-TV blunder of all time, producer Jordan Horowitz stopped mid-speech to declare, “There’s been a mistake. *Moonlight*, you guys won Best Picture.” Cue collective gasps, awkward shuffling, and a lot of confused faces. The moment was as chaotic as it was iconic, and while *Moonlight* deservedly took its place in history, the fiasco overshadowed their win. The Oscars haven’t been that shocking – or uncomfortable – since.

Cropped Ellens celebrity selfie — 2. The Selfie That Broke the Internet (2014)

Ellen DeGeneres didn’t just host the Oscars in 2014 – she made internet history. Armed with a Samsung phone and a star-studded crowd, she wrangled A-listers like Meryl Streep, Bradley Cooper, and Jennifer Lawrence into what would become *the* celebrity selfie to end all selfies. It was chaotic, a little blurry, and packed with more star power than most films, and Twitter absolutely ate it up. The photo became the most retweeted post in history (at the time), and Ellen officially set the standard for what an “Oscars moment” could be. Sure, it was a shameless plug for Samsung, but hey, when the result is that fun, who’s complaining?

Cropped Will Smith slaps Chris Rock — 1. The Slap Heard ‘Round the World (2022)

The 2022 Oscars were rolling along like usual – until they weren’t. When Chris Rock made a joke about Jada Pinkett Smith’s shaved head, Will Smith walked up to the stage and *slapped him*. Yes, slapped him. On live TV. The world collectively froze as Smith returned to his seat and yelled, “Keep my wife’s name out your f****** mouth!” The room was silent, the internet exploded, and suddenly the Oscars turned into a reality show. Moments later, Smith won Best Actor for *King Richard*, giving a tearful, awkward speech about protecting his family. It was a moment no one saw coming, and it overshadowed pretty much everything else that happened that night. Love it, hate it, or meme it – it’s a moment we’ll never forget.

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The Oscars are more than just Hollywood’s biggest night – they’re a cultural phenomenon, a stage where magic, mishaps, and unforgettable moments unfold in front of millions. Over the years, the Academy Awards have given us more than just golden statuettes and glamorous red-carpet looks; they’ve delivered shocks, laughs, tears, and controversies that have become legendary in their own right. From history-making wins to viral mishaps and everything in between, these moments have cemented their place in pop culture.

In this list, we take a look back at the top 20 unforgettable moments in Oscars history – those rare instances that left the world talking, gasping, or cheering. Whether you’re a cinephile or just someone who loves a good spectacle, these iconic highlights will remind you why the Oscars remain the gold standard for awards shows. Let’s dive in!