21 Historically awkward moments from the Oscars

Tonight is the 88th Academy Awards and in light of this, I decided to take a look back at some of the most awkward moments from the night across the years. Expect to see moments from the likes of John Travolta, Angelina Jolie and of course, Sean Penn.

1. Rob Lowe sings (1989)

Starting off back in 1989, AKA before you or I were born, Rob Lowe and Snow White sang the Flamingo’s ‘I Only Have Eyes For You’ and a compilation of other songs awfully. An off-key Lowe sang the duet with actress Eileen Bowman as part of an elaborately hokey musical medley that lasted more than ten minutes and left seated stars such as Dustin Hoffman, Robert Downey Jr. and Sigourney Weaver scratching their heads in confusion.

How bad was it? Disney filed a lawsuit against the Academy for unauthorised use of its character. You have to wonder who asked for this kind of thing at the Oscars?

2. David Letterman’s Oprah-Uma joke (1995) 

Moving on to 1995 and it seems David Letterman wasn’t so perfect after all. In 1995, David Letterman was tapped to host the Oscars, but his irreverent humor failed to mesh with the grand tone of the event. Most awkward of all his jokes was a bizarre gag in which he jokingly introduced Oprah Winfrey to Uma Thurman from the stage (say it with us: “Oprah…Uma… Uma…Oprah”). He’s lucky he held on to The Late Show after this.

3. The time Angelina Jolie kissed her brother on the red carpet (2000)

That Oscar trophy wasn’t the only one smooched by Angelina Jolie’s famous lips at the 72nd Academy Awards. The actress planted a kiss on older brother James Haven with a force that set rumor-mongers atwitter with word of an incestuous relationship. It didn’t help that the excited Jolie launched into her acceptance speech for her supporting role in Girl, Interrupted with an ode to her sibling: “I’m in shock, and I’m so in love with my brother right now,” she giggled. “He just held me and said he loved me and I know he’s so happy for me.” Amongst her recent humanitarian work this is often forgotten, but I think this is why I was always proudly on #TeamJen.

4. South Park creators attended the awards high and in drag (2000)

South Park creators Trey Parker and Matt Stone, were tickled by the idea of showing up to the 2000 Oscars mimicking some legendary red-carpet looks (namely Jennifer Lopez’s belly-button-baring gown at the 2000 Grammys and Gwyneth Paltrow’s 1999 Oscar get-up). We later found out that the duo took drugs to muster up the courage. “It’s really important we set the record straight,” they told Jimmy Kimmel in 2011. “We were on acid.” If it takes illegal substances to merit the stunt, perhaps it wasn’t worth it to begin with although they did look better in those outfits than most females would.

5. Bjork laid an egg on the red carpet (2001)

What is it with weird acts on the red carpet? Surely your publicist is better than that. Icelandic musician Bjork’s 73rd Academy Awards dress is not only one of the most iconic red carpet outfits ever (the ruffled number even has its own Wikipedia page), but also among the most awkward. It’s often seen on worst dressed lists. Folks who thought she dropped her clutch while walking toward the ceremony venue were surprised to see she dropped a sizeable egg, on purpose, out of her swan dress. We’ll let you argue about how good she looked in the ensemble, but we will say this: Bjork’s Oscar cameo sure reminded us of Hans Christian Andersen’s tale of a duckling that didn’t quite fit in.

6. Michael Moore bashes President Bush (2003) 

Most winners don’t even have time to finish their thank-yous before the cut-off music switches on, but filmmaker Michael Moore managed to squeeze in a whole political rant after snagging a best documentary win for Bowling for Columbine. “We live in the time where we have fictitious election results that elects a fictitious president,” he said to an A-lister crowd that quickly took sides. The boos and cheers were very, very audible. I suppose you know you’re doing your job if a filmmaker slags you off at the awards, right?

7. Adrien Brody makes out with Halle Berry (2003)

Apparently, when overcome with happiness, actor Adrien Brody’s primal instinct tells him to latch his lips onto the pretty woman who gave him the news. Brody took everyone by surprise (especially Berry) when he enveloped the actress in his arms for a long, bending kiss after winning a lead actor Oscar for The Pianist. If this is how he says thank you, can I present him with his next award?

8. Sean Penn as ever doesn’t get the joke (2005)

The 77th Academy Awards assigned stand-up comedian Chris Rock to the hosting post, foreshadowing a night of ruder-than-usual digs at celebrities for laughs. Take this for example: “Who is Jude Law? Why is he in every movie I have seen in the last four years? Even if he’s not acting in it, if you look at the credits he makes the cupcakes or something.” Perhaps actor Sean Penn thought that Law forgot his armour, stepping onstage to defend his peer before presenting the lead actress award. “Forgive my lack of humour,” Penn responded. “Jude Law is one of our most talented actors.” #AwkwardTurtle

9. Gary Busey hijacks a red carpet interview (2008) 

After three years of a dry spell of awkward moment you can always rely on Busey to bring them back. Red carpet reporter Ryan Seacrest just wanted to interview Laura Linney and Jennifer Garner, but Gary Busey was not having any of it. Busey first called out to Seacrest as he was calling Garner and Linney over, delaying the start of the interview. Then, after everyone continued, assuming the incident was over with, Busey came back addressing Linney for a second interruption. The moment gets even stranger after Seacrest directs Busey’s attention to Garner, whom Busey then surprises with a hug and a kiss on the neck.

10. Market Irglová’s speech is cut off (2008)

When Glenn Hansard and Market Irglová won the award for original song for ‘Falling Slowly’ at the 80th Academy Awards, both were overcome with emotions. Hansard took the mic first to give his thanks as they accepted their statuettes. When Irglová leaned in to give her own thanks, the show cut her off with music before she could get a word out, forcing her to awkwardly make her way off the stage with her musical partner. Ever the gentleman, host Jon Stewart later called Irglová back on stage so she could give her speech and have her well-deserved Oscar moment.

11. An awkward reunion between Brangelina and Jen (2009)

Brad Pitt and Jennifer Aniston ended their five-year marriage in 2005 amid reports that Pitt was romantically linked to Angelina Jolie. The 81st Academy Awards was the first time all three were publicly present in the same room: Both Pitt and Jolie had acting nominations and Aniston was a presenter. In fact, Aniston presented her awards directly in front of Pitt and Jolie, who were seated centre stage. The three put a new meaning to the words “grin and bear it” by appearing to exchange smiles throughout the awkward arrangements.

12. James Franco and Anne Hathaway host (2011) 

In a ploy to attract a younger audience, actors James Franco and Anne Hathaway were paired to host the 83rd Academy Awards. Unfortunately, most people agreed that the show was a bust. Hathaway gave an honest effort, and even looked like she was trying to overcompensate for Franco, who at best could be described as not mentally present. Franco tried to defend his performance to David Letterman, saying that his former co-host was “so energetic, I think the Tasmanian Devil would look stoned standing next to Anne Hathaway.” I’d put a video here but it’s just too awkward to put you all through that.

13. Billy Crystal’s impersonates Sammy Davis Jr. (2012)

The 84th Academy Awards hit a hurdle when producer Brett Ratner resigned to making homophobic and other controversial remarks; in the aftermath, Ratner’s planned host, Eddie Murphy, stepped down. Nine-time host Billy Crystal seemed like a safe choice for the Academy to steer away from any additional controversy.

Unfortunately, when Crystal fell back on an old bit impersonating Sammy Davis Jr. during his opening number, he learned the hard way that viewer sensibility about donning blackface has significantly changed since the 1990s. Later in the ceremony, after Octavia Spencer won the award for supporting actress, Crystal joked: “After I saw The Help I just wanted to hug the first black woman I saw. Which from Beverly Hills is about a 45-minute drive.” For many, these racially charged moments missed the mark.

14. The Dictator attacks Ryan Seacrest (2012) 

Thwarting efforts from the Academy to stop him, Sacha Baron Cohen walked the red carpet of the 84th Academy Awards in character as General Aladeen from The Dictator. Flanked by supermodel body guards, he also carried a golden urn that he claimed contained the ashes of former North Korean leader, Kim Jong-Il. During a red carpet interview, Baron Cohen surprised Ryan Seacrest by emptying the urn all over him, taking this publicity stunt to a new level.

15. Jennifer Lawrence falls and becomes a meme forever (2013)

Jennifer Lawrence proved she is just as human as the rest of us when she tripped on the stairs on her way to accept the best actress Oscar at the 85th Academy Awards. After making it to the stage with a standing ovation, she confronted the situation head-on by saying, “You guys are just standing up because you feel bad that I fell and that’s really embarrassing, but thank you.”

16. Seth Macfarlane hosts and insults the majority of the audience (2013)

The Academy took a gamble when they let Seth MacFarlane host the 85th awards, counting on his star power from TV to draw in a larger audience for the telecast. What they perhaps did not count on, however, was his brand of television humour not being better received on cinema’s biggest night. Some people considered the many moments that MacFarlane relied on jokes about race or women inappropriate for the occasion. His cringe-worthy opening number, ‘We Saw Your Boobs,’ a song that diminished actresses and their work to their moments of on-screen nudity, set the tone for the night.

17. Liza Minelli misses out on the most famous selfie (2014)

The 86th Academy Awards was a night filled with poignant, milestone-setting moments — that Liza Minnelli wanted in on.  Mid-show, host Ellen DeGeneres rounded up some high-profile celebs for a selfie that shattered records (and servers) with more than 3 million retweets. What fans missed in the image is Minnelli joining the huddle from behind, too short to be seen.

Later, as Lupita Nyong’o made her way to the stage for her supporting actress win, Minnelli jumped up to snag an embrace … before some of Nyong’o’s other cast members could.

18. John Travolta introduces ‘Adele Dazeem’ (2014)

John Travolta was tasked with introducing Idina Menzel before her performance of the Oscar-nominated (and later Oscar-winning) song ‘Let It Go’ from Frozen at the 86th Academy Awards. Unfortunately, he ended up introducing ‘Adele Dazeem’ in what would become the flub of the night. Ever the professional, Menzel still nailed her performance, although Travolta would never live it down.

19. Someone doesn’t approve of Fifty Shades of Grey (2015)

During a red carpet interview, actress Melanie Griffith admitted that she had not yet seen daughter Dakota Johnson’s performance in Fifty Shades of Grey, implying that she was uncomfortable with some of the scenes she would see. When Griffith continued to refuse even the possibility of watching the film, a flustered Johnson responded “All right! You don’t have to see it!”

20. Sean Penn’s green card joke (2015)

Seriously this guy just needs to stop. When Sean Penn opened the envelope to announce the best picture at the 87th Academy Awards, he asked, “Who gave this son of a … his green card?” before revealing Birdman as the winner. In a year when the Oscars were being scrutinized for the lack of diversity among the nominees in the top categories, some felt Penn’s joke about director Alejandro G. Iñárritu’s nationality fell flat.

21. John Travolta gets ignored for a kiss (2015): 

There’s no doubt she looked irresistible in her emerald green gown, but Scarlett Johansson was rather taken aback by a certain admirer’s advances on Oscar night.

The 30-year-old actress was posing for photographs on the Academy Awards’ red carpet when John Travolta, 61, crept up from behind to plant a big smacker on her cheek. Although Johansson eventually went on record to clean up the confusion, the 2015 Oscars was not Travolta’s night.

There’s bound to be plenty of new awkward moments from tonight’s 88th Academy Awards but until then, feel free to watch the most awkward Oscars performance of all time, delivered by Seth Macfarlane.