What Was the Weirdest Oscars Ever?

Once upon a time in Hollywood—fine, 1953 if you want to be specific—the Academy Awards were televised for the first time in its 25-year history. More than 40 million people tuned in to watch Gary Cooper win Best Actor and Shirley Booth win Best Actress. Presenters included Ronald Reagan, Walt Disney, and Frank Capra. Host Bob Hope had to dress in a blue shirt under his dinner jacket because white would have been too bright for cameras. The last award presented was a lifetime achievement honor. And in a gasp-inducing upset, the classic Western High Noon lost to Cecil B. DeMille’s bloated extravaganza The Greatest Show on Earth for Best Picture.

The big show would only become weirder from there.

When we reminisce about the most memorable moments in Oscar history, there’s no nostalgia for, say, the time Anthony Hopkins and Jodie Foster won in their respective categories for The Silence of the Lambs in 1992. We expect the truly talented to triumph at an awards show. After a while (let alone 91 years), the deserved winners all meld into one breathless, teary-eyed celebrity clad in Armani. Nobody can instantly name-drop the Best Supporting Actress winner when David Letterman hosted in 1995 except Dianne Wiest herself and maybe the four also-rans. But everyone remembers how Letterman fixated on Uma Thurman’s and Oprah Winfrey’s names in his monologue. Because it was weird. The weird is what makes the Oscars great.

Please don’t envision a bunch of A-listers clamoring to take a selfie with Ellen DeGeneres right now. That was a mildly risky hosting gimmick with a massive payoff. If Julia Roberts and Bradley Cooper et al. had stayed glued in their seats instead, then we’d be in business. True weirdness is to witness an unscripted, delightfully cringey WTF moment that makes you glad to be alive.

How fortunate that an Oscars ceremony naturally lends itself to the art form. Start with the fact that countless famous people must share oxygen in the same windowless room. Then consider the seating arrangement. Unlike at the Golden Globes or the SAG Awards, these celebrities don’t get the luxury of sitting at round tables and yakking it up with their pals. There are no plates of crunchy vegetables and savory carbs on their plates or endless champagne flowing like magic. Oscar attendees are visibly uncomfortable in a chilly auditorium and starving and nervous as hell. That combination is bound to manifest itself into dazzling peculiarity. Our nominees stew in those plush chairs and know deep down that expert prognosticating only goes so far. Spoilers will always be de rigueur thanks to ever-changing tastes in the industry. (Just last year, the old-fashioned Green Book triumphed over the bolder Roma and Black Panther, and it was deemed an upset.) And, of course, every shocker is captured on TV cameras and broadcast to a billion people around the world. This only adds to the pressure, which in turn increases the likelihood of goofs, bad judgment calls, and overall oddness in a glorious three-plus-hour span.

But what was the weirdest ceremony of all? A bit of YouTube research and historical perspective are required to arrive at the answer. Dare I say the breakneck competition ranks right up there with the Best Picture race in 1996, when Braveheart bested Apollo 13, Babe, The Postman (Il Postino), and Sense and Sensibility. Without further ado, let’s get on with the show.

The Nominees

The Year Angelina Jolie Made Us Squirm (2000)

“I’m in shock ... and I’m so in love with my brother right now!”

This was how Angelina Jolie began her acceptance speech as Best Supporting Actress for her role as an institutionalized wild child in Girl, Interrupted. The declaration for James Haven—in tandem with her daughter-of-Elvira goth look—served as an early indication that Jolie wasn’t like the rest of us. And, you know, most people find light incest to be … disconcerting. To move from wince to whoa: Later that night, Robin Williams gleefully sniped about “there’ll be no more Celine Dion” in the raucous “Blame Canada” musical number from South Park: Bigger, Longer and Uncut. The song lost out to a Phil Collins ballad from Tarzan. Welcome to the millennium!

The Year Ansel Elgort Shot Hot Dogs Out of a Cannon (2018)

Ah, there’s nothing like a host stunt gone fantastically awry. In 2018, Jimmy Kimmel gathered a crew of celebrities and took a field trip to a nearby movie theater to surprise an unsuspecting audience mid-screening. Lin-Manuel Miranda, Margot Robbie, and Emily Blunt were among the volunteers. Mark Hamill used the downtime to fawn over Gal Gadot. What happened next was total unglamorous madness, as director Guillermo del Toro—who would win Best Director in an hour’s time—carried in a giant sub sandwich with Miranda, Gadot handed out candy, and Armie Hammer and Ansel Elgort armed themselves with fully functional hot dog cannons. It remains unclear whether the theatergoers were psyched about their brief brush with stardom or just thought it was just a tripped-out scene from A Wrinkle in Time.

The Year of the Streaker (1974)

He had a name, you know. Robert Opel was an American photographer/protester. (Read: a hippie.) He got backstage via a press pass, stripped down to his birthday suit, and dashed across the stage while flashing a peace sign just as upper-crust British actor David Niven was about to introduce his cohost Elizabeth Taylor. Niven’s pitch-perfect observation: “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?” Opel was never arrested and admitted the act was performance art in a conformist society. He was murdered in his art studio in San Francisco five years later.

The Year of the Marisa Tomei Shocker (1993)

The show was dubbed “The Year of the Woman,” even though only one female had ever been nominated for Best Director. (Props to Lina Wertmüller; no props to the Academy.) The woman of the night turned out to be Marisa Tomei, once known as Denise Huxtable’s white roommate on A Different World for one season—that is, until she played an out-of-work hairdresser and automotive savant in My Cousin Vinny. Tomei not only won in a comedy role—a true Oscars rarity and no, Jennifer Lawrence’s turn in Silver Linings Playbook doesn’t count—she beat some legit acting legends, including Joan Plowright and Vanessa Redgrave. The win was so out there that for years, she was dogged by a bizarro conspiracy theory that elderly presenter Jack Palance had read the last alphabetical nominee instead of the actual winner. In other female-related news from that night, Nell Carter busted out “Friend Like Me” from Aladdin in a Debbie Allen–choreographed production number instead of star Robin Williams. Blame Canada?

The Year of Adele Dazeem (2014)

What are we going to do about John Travolta? The man is an icon, no matter how he combs his “hair.” But he doesn’t make it easy for his fans, and not just because of his Battlefield Earth and Gotti two-fer. At this ceremony, all he had to do was introduce Idina Menzel so she could sing “Let It Go” from Frozen. Granted, she’s no Olivia Newton-John in terms of familiarity. Still. The name rolls off the tongue. Instead he blew off the teleprompter and went rogue, and audiences had to momentarily wonder whether British crooner Adele and some other dude were part of the Frozen cast. Ellen’s group selfie and her pizza-delivery-to-the-audience gimmicks aside, this botch defined the 2014 ceremony. Also that year? The worst photobomb you’ve ever seen:

Getty Images

The Year of the Crash Controversy (2006)

This one still hurts. Ang Lee had just won Best Director for Brokeback Mountain. The lovely drama depicting a heartbreaking romance between two adrift cowboys—and led all movies with eight nominations, none technical—was poised to take it all. This would be a groundbreaking victory, a signal of true progression in Hollywood. Alas, the older Academy members felt more comfortable handing Best Picture to ... Crash, the heavy-handed drama that examined bigotry in the thinnest way imaginable. The only consolation was hearing presenter Jack Nicholson say the word “crash” as if he had just watched Magic Johnson miss a jump shot in the NBA Finals circa 1989.

The Year of Sacheen Littlefeather (1973)

No surprise here: Marlon Brando wins Best Actor for playing mafia don Vito Corleone in The Godfather. He deserves it. Wait, who is that woman ascending the stage and brushing off presenters Roger Moore and Liv Ullman, and why is she dressed like that? Her name was Sacheen Littlefeather—an actress also known as Marie Cruz—and she read off a prepared statement as to why Brando would not be accepting his second Oscar. Excerpt: “He has asked me to tell you … that he very regretfully cannot accept this very generous award. And the reasons for this being are the treatment of American Indians today by the film industry.” Cue grumbling from the audience. Cue co-host Rock Hudson, who sniped, “Often to be eloquent is to be silent.” A few moments later, Liza Minnelli took Best Actress for Cabaret. She happily accepted.

The Year of Uma/Oprah (1995)

The theme was comedy. Tim Curry, Kathy Najimy, and little Mara Wilson—presumably, their names were picked out of a top hat at random—started off the night with a song-and-dance rendition of “Make ’Em Laugh,” which suffered from miscalculated timing because latecomer Jessica Lange and her party stood up and blocked the shot. Perhaps this flub was a harbinger of doom for David Letterman, who was just three minutes into his monologue when he remarked, “I’ve been dying to do something all day and I think maybe we can take care of this.” Ask Tommy Lee Jones why he had shaved his head? Nope. He gestured between Oprah Winfrey and Uma Thurman in the front rows and bellowed, “Uma ... Oprah.” Excruciatingly long pause. “I feel much better. Have you kids met Keanu?” The gig careened downhill from there, as the host flailed with a Top Ten List about signs the movie you’re watching will not win an Academy Award—“Four words: Dom DeLuise is Gandhi” was no. 1—and a taped sketch in which Alec Baldwin and Rosie O’Donnell mocked his cameo in the flop Cabin Boy. The first day he returned to The Late Show, a self-deprecating Letterman quipped, “In retrospect, looking back on it, I had no idea that thing was televised.”

The Year of the Halle Berry Kiss (2003)

The 75th ceremony was shaky even in the windup because of the American invasion of Iraq. The red carpet festivities were curtailed; the bleacher seats for the screaming fans were removed. Cate Blanchett, Jim Carrey, and Will Smith pulled out as presenters out of respect for the military. But the show went on as scheduled … with unscheduled moments galore. Oh, sure, human lightning rod Michael Moore received a shower of boos when he expressed his disgust of the “fictitious” war in his acceptance speech for Best Documentary for Bowling for Columbine. (Host Steve Martin deadpanned, “Right now, the Teamsters are helping Michael Moore into the trunk of his limo.”)

But to quote Al Pacino in his Oscar-winning turn in Scent of a Woman, I’m just getting warmed up! In a mild shocker, Barbra Streisand announced that the Oscar for Best Original Song went to “Lose Yourself” from 8 Mile. Because Eminem was a no-show, co-songwriter Luis Resto accepted the trophy ... wearing a red Detroit Pistons jersey under a grey blazer that he may or may not have slept in the night before. Cameron Diaz was caught chomping on gum and playing with her hair during his 30-second acceptance speech. Meanwhile, presenter Harrison Ford—after being the guy who handed out Best Picture the year Shakespeare in Love beat Saving Private Ryan—was again left dumbstruck at the podium, this time for revealing that exiled Roman Polanski had won Best Director for The Pianist. The weirdness culminated when Adrien Brody triumphed over vets Jack Nicholson, Michael Caine, Daniel Day-Lewis, and Nicolas Cage for Best Actor. After swearing on camera, he jumped to the stage and almost swallowed presenter Halle Berry whole with a prolonged kiss. “I bet they didn’t tell you that was in the gift bag,” he crowed. She went with it, but recently admitted to Andy Cohen, “I was like, ‘What the f--- is happening right now?” Same.

The Year of Envelope-gate (2017)

Look, there are goofs, and there are epic fails for the ages. Let’s re-examine what happened during the bonkers closing moments of an otherwise ho-hum telecast, shall we? It will be cleansing! In honor of Bonnie and Clyde’s 50th anniversary, costars Warren Beatty and Faye Dunaway reunite to present Best Picture. Beatty opens the envelope, vamps for a few secs, looks befuddled, and gives it to Dunaway. She reads “La La Land” with conviction. OK, why not; the musical was a front-runner and director Damien Chazelle had just won Best Director. The “City of Stars” orchestration swells, drowning out Beatty as he remarks to Dunaway, “It says ‘Emma Stone.’”

As the producers deliver their earnest speeches, a frantic commotion is evident on stage. “We lost by the way,” Fred Berger says at the end of his speech. La La Land coproducer Jordan Horowitz snaps out of the denial phase to step up and announce ... wait for it ... “There’s been a mistake!” Poignant indie Moonlight is the true winner, and Horowitz yanks the correct card out of Beatty’s hands and holds it up to the crowd (and the cameras) for proof. Audiences all over the world and inside the Dolby Theatre—front row-ers Nicole Kidman, Michelle Williams, and Meryl Streep, among them—now attempt to register the fact that the Oscars just pulled a Miss Universe. Chazelle lingers in the background looking like he’s been caught stealing from his parents’ liquor cabinet. An indignant Beatty, likely foreseeing a ding on his movie-star legacy, insists on giving an explanation: He saw “Emma Stone, La La Land” on the card in the envelope, paused in confusion, and gave it to his partner-in-crime. “I wasn’t trying to be funny!” he proclaims. Director Barry Jenkins finally accepts the big award for Moonlight and does so without his head literally exploding. First-time host Jimmy Kimmel closes the show and jokes that he knew he’d screw up the gig somehow. And ... scene!

Playing conspiracy theorist and trying to figure out who pulled the strings to make this happen was fun while it lasted. Now we know that a distracted accountant from Ernst & Young gave the stars the duplicate Best Actress envelope by accident, resulting in the error. One year later, Beatty and Dunaway did a make-good and presented Best Picture without a hitch. Bo-riiiing.

And the Weirdest Oscar Ceremony award goes to …

The Year of Snow White and Rob Lowe (1989)

Do you have 11 minutes and 31 seconds to spare? If so, I demand you type “Snow White 1989 Oscars” into Google and watch the magic happen. Let’s just say it makes Envelope-gate look like an off-camera sneeze. In a hostless Oscars, a squeaky-voiced actress dressed up like the Disney princess opened the show—and the fact that she wore ruby-red slippers despite zero connection to The Wizard of Oz was the least of her problems. Squeal in amazement as Snow White, singing “I Only Have Eyes for You,” saunters into the audience and forces a reluctant Michelle Pfeiffer to hold her hand. Tom Hanks can’t mask his horror. Then amuse yourself as the stage opens to reveal a Coconut Grove set (Wiki it), where former talk-show host and game-show producer Merv Griffin warbles “I’ve Got a Lovely Bunch of Coconuts” to confused Hollywood legends such as Vincent Price and Dorothy Lamour assembled at makeshift tables.

Deep breath, for now we’ve reached the pièce de résistance: Rob Lowe—four years removed from his Brat Pack peak in St. Elmo’s Fire—appears on stage as Snow White’s blind date. Apparently Snow can’t see or hear: The two proceed to duet in an off-key rendition of Creedence Clearwater Revival’s “Proud Mary” in its entirety with all-new lyrics like “Big lights keep on burning / Cameras keep on turning.” John Fogerty was rolling in his grave even though he’s still alive and well.

Friends, that was just the opener of the Weirdest Oscars Ever. Show producer Allan Carr was generous to provide us with a chaser. In a special eight-minute production midshow, “Nineteen of the hottest young people in pictures”—co-presenter Bob Hope’s words—sang and danced to an original song called “(I Wanna Be an) Oscar Winner.” Corey Feldman Moonwalked in a leather jacket. Christian Slater and Tyrone Power Jr. played pirates and fought for Ricki Lake’s hand. Patrick Dempsey tapped and twirled a baton. Holly Robinson and Blair Underwood sang at the podium. Matt Lattanzi and Corey Parker danced and then likely joined the Witness Protection Program. The actual hottest young people in Hollywood—i.e., Johnny Depp, Keanu Reeves, John Cusack, and Winona Ryder—probably laughed their asses off at home while Best Supporting Actor nominee River Phoenix had to suffer through it from his seat in the audience. To this day, none of the participants of this performance have been nominated for an Oscar. Though it should be noted that Disney is going forward with a live-action version of Snow White.

Mara Reinstein is a New York City–based film critic and entertainment journalist who contributes to Us Weekly, Billboard, The Cut, HuffPost, and Parade.