When a joke bombs during the Academy Awards ceremony, it bombs hard. It's not like an open-mic night at some comedy club, where at most you're going to humiliate yourself in front of a few dozen people. The Oscars are watched by an estimated 33 million people (as of last year), and not all of them are rooting for the rich and handsome entertainers. Believe it or not, some people actually want them to fail, so they can go on Twitter and express their dismay. How many jokes have been told at the Oscars over the past 88 years? Thousands, probably. But the only ones we remember are the jokes that bit the dust.
Here are 30 jokes that some very talented individuals tried to make work during their respective moments of Oscar glory, but which ended up being the mistake they're still trying to live down. Ah, celebrity schadenfreude, is there any better way to distract ourselves during a workday? To revel in even more awkward award show banter, check out the 30 Most Awkward Celebrity Awards Show Moments.
1 | Letterman introduces Uma and Oprah.
David Letterman hosted the Oscars only once, in 1995, and with good reason. We loved the acerbic late night host in his regular gig, but his sense of humor just didn't translate to prime time. Case in point, the Uma... Oprah... Uma... Oprah..., bit. "I feel much better," he said afterwards. Well, that makes one of us.
2 | Chevy Chase welcomes the phonies.
Chevy Chase was a superstar in 1988, thanks to blockbusters like National Lampoon's Vacation and Fletch, so there was a lot of excitement for his second stint as an Oscar host. But when he opened the show with "Good evening, Hollywood phonies," it was all downhill from there. He came across as smug, smarmy, and not all that funny. For jokes that won't fail like this one, take inspiration from one of The 28 Wittiest Put-Downs Ever Uttered.
3 | James Franco wears a dress.
Most of the jokes attempted by James Franco and Anne Hathaway while co-hosting the Oscars in 2011 landed with a thud rather than a giggle, but the cross dressing was especially cringe-worthy. Even Franco regrets dressing up like Marilyn Monroe in Gentlemen Prefer Blondes. "I was so [angry] about that, I was deliberately going to fall onstage and hopefully my dress would fall off or something—they couldn't blame that on me," he said of the costume. That might've been funnier.
4 | Billy Crystal wears blackface.
Crystal was one of the best hosts in Oscar history, but he made a rare misstep in 2012 when he played Sammy Davis Jr. in full blackface. It wasn't a new character for him, but maybe not the best choice for a modern crowd. As the New York Times' Dave Itzkoff tweeted, "If you had three minutes for First Blackface of the Night in your #Oscars pool, congratulations!" And for more silly humor, don't miss these 50 Puns So Bad They're Actually Funny.
5 | Seth MacFarlane misses target with Lincoln joke.
Seth MacFarlane didn't win over any new fans after hosting the Oscars in 2013. And weirdly, one of his biggest flops of the night was a gag about a political assassination that happened two centuries ago. "The actor who really got inside Lincoln's head was John Wilkes Booth," MacFarlane said, which got a cold reaction from the crowd. The host, perplexed by the jeers, wondered aloud, "Is 150 years too soon? If you don't like that, I've got some Napoleon jokes to tell you." For jokes that won't bomb, take a look at the 50 Jokes That Are So Bad They're Actually Funny.
6 | Jimmy Kimmel brought tourists to the Oscars.
Jimmy Kimmel's sense of humor can be an acquired taste, like when he invited a Hollywood Stars coach tour of people into the Oscars ceremony in 2017 to see the stars up close and personal. What started as mildly funny dragged on a bit too long, until even the tourists wanted to get the heck out of there.
7 | Sean Penn's green card razzing.
Before revealing the best picture winner in 2015, Sean Penn asked the crowd, "Who gave this son of a [expletive] his green card?" He was referring to Birdman director (and Mexican citizen) Alejandro González Iñárritu. Maybe not the time and place to be making cracks about immigration.
8 | Jerry Lewis kills time.
In 1959, the unthinkable happened. The Oscars ended early. Twenty minutes early, no less. With all that air time to fill, co-host Jerry Lewis did his best to improvise, orchestrating a very awkward and uncomfortable dance party and playing the trumpet (badly). It was so excruciating that Time writer Richard Corliss once compared it to the 18-minute gap on the Watergate tapes. And if you're looking for more laughs, check out the 40 Facts So Funny They're Hard to Believe.
9 | Stacey Dash… director of minority outreach?
When 2016 Oscar host Chris Rock introduced Clueless actress (and outspoken conservative) Stacey Dash as the director of the Oscar's minority outreach program, it was a confusing joke. Was he making fun of her politics? Dash just double-downed on Rock's crack, telling the audience, "I cannot wait to help my people out. Happy Black History Month!" Nobody in the audience knew quite how to react.
10 | Neil Patrick Harris's magic box.
Neil Patrick Harris had more than a few comedic duds during his Oscar hosting experience in 2015, like a cringe-inducing gag about Edward Snowden being absent "for some treason," but the worst was probably his Oscar predictions, locked in a clear box and over-explained throughout the evening. We get it, Neil, you really wanted to be a magician. There's a time and place for that. If your magic trick takes longer to explain than one of the acceptance speeches, maybe you save it for a dinner party at your house. (Although in his defense, we're still amazed with how he pulled it off.) And for more on Hollywood, check out the 50 Crazy Celebrity Facts You Won't Believe Are True.
11 | Dudley Moore, Richard Pryor, and Walter Matthau try (and don't succeed) to sing.
Even if you're an immensely talented actor and comedian, you need to rehearse, especially if it's a skill set that you don't usually excel at. Apparently nobody mentioned this to 1983 Oscar co-hosts Dudley Moore, Richard Pryor, and Walter Matthau, who clearly weren't prepared to perform a song-and-dance number called "It All Comes Down To This" with Liza "I'm the only one here who knows what she's doing" Minnelli. We've seen elementary school plays with better efforts.
12 | Bob Hope goes dark.
Bob Hope hosted the Oscars a record 19 times between 1939 and 1977, so it's kind of a miracle that his jokes succeeded as often as they did. The only example we could find of Bob delivering a clunker was in 1955, when he tried out a gag that may've been too grim for the celebration. "The winners will take home an Oscar," he said. "The losers will all be presented with monogrammed do-it-yourself suicide kits." Yikes. Take it easy, Bob!
13 | Melissa Leo needs a cane.
It's not Melissa Leo's long and rambling acceptance after winning Best Supporting Actress for The Fighter in 2011. It's why she felt compelled to grab presenter Kirk Douglas's cane and use it to leave the stage while impersonating an old lady. Maybe she wasn't making fun of the 101 year old stroke survivor, but it was still in poor taste. And for some humor in truly excellent taste (at least we think so), try reading the 30 Most Hilarious Bill Murray Encounters.
14 | John Travolta can't stop touching Idina Menzel's face.
After John Travolta botched the name of singer Idina Menzel at the 2014 Oscars, calling her "Adele Dazeem" for some reason, he tried to make up for it the following year… by touching her face a lot. He seemed to think he was being cute — he kept doing it, after all — and his weird cooing was clearly some kind of joke that made sense only to him. "I deserve that, but you, you, my darling, my beautiful, my wickedly talented Idina Menzel—is that right?" Please, for all of America, we're begging you, Mr. Travolta. Just stop! And to keep the laughs coming, don't miss the 20 Things Everyone Secretly Finds Hilarious.
15 | Donald Duck, Oscar host.
No video footage exists (that we could find) of this historic event in 1958, the first (and hopefully last) Oscar host to greet the Hollywood elite while not wearing pants. Hey, we get it, that's Donald's thing, but this is a family show.
16 | Roberto Benigni wants to be your special someone
Roberto Benigni was undeniably charming when he won two Oscars for Life is Beautiful in 1999, for Best Foreign Language Picture and Best Actor. As he explained during one of his speeches, he'd used up all of his English. But that didn't stop him from trying to express his gratitude anyway, with the strange admission that he wished he was like Jupiter, so that he could "make-a love to you all in the firmament." Um… could we pass on that?
17 | Letterman mocks Susan Sarandon and Tim Robbins
"Uma/Oprah" wasn't Letterman's only bomb at the 1994 Oscars. He also tried (and failed) to rib presenters Susan Sarandon and Tim Robbins, a politically outspoken couple who had used their Oscar time two years earlier to talk about Haitian refugees held in U.S. detention camps. "Pay attention," Letterman quipped. "I'm sure they're [angry] about something." It might've been meant in good fun, but it came across mean-spirited.
18 | Chris Rock is not impressed by Jude Law
Most of Chris Rock's material as Oscar host in 2005 was right on target, save for a joke that came at Jude Law's expense. In a bit where Rock explained why directors shouldn't cast lesser talent, he said, "If you want Tom Cruise and all you can get is Jude Law, wait!"
It wasn't Law who took the jab personally, but Sean Penn, who expressed his dismay before announcing the Best Actress Award winner. "Forgive my compromised sense of humor," Penn said, "but I did want to answer our host's question about who Jude Law is. He's one of our finest actors."
19 | Ellen calls Liza Minnelli a man
Ellen DeGeneres usually lobs softballs at her targets, so it was surprising when, as Oscar host in 2014, she went after Liza Minnelli. Pointing out the legend in the audience, Ellen introduced her as "one of the most amazing Liza Minnelli impersonators." Then, to make sure the insult was really driven home, she added, "Good job, sir."
Minnelli revealed later that she hadn't taken the joke in stride. "I was really fine until she said ‘sir.' And then I thought, 'Ouch! Ouch'." And for more fun with celebs, here are the 30 Funniest Celebrity Commercials That Will Leave You in Stitches.
20 | Shirley MacLaine thanks her past lives
Shirley MacLaine had a lot of people to thank when she won a Best Actress in 1984, for Terms of Endearment. Many, many, many people. Including people she'd known "in the other life I might have had" who MacLaine suspected might have "something to do with this." Her fascination with past lives and reincarnation were already well known, but her little Oscar joke just fell flat and awkwardly.
21 | Jimmy Kimmel feeds the audience
Bags of red vines and junior mints raining down from the ceiling at the 2017 Oscars is funny in theory. But when the candy lands on actors who've all starved themselves to fit into their ridiculously tight clothes, and then host Jimmy Kimmel taunts them with "time to find out how well those spanks really work," the whole thing felt more awkward and uncomfortable than funny.
22 | Paul Hogan reminds the audience what's at stake.
Crocodile Dundee star Paul Hogan says he had no script or rehearsal before greeting the Oscar audience in 1987 and giving them pointers on Oscar etiquette. And to be honest, it shows. He encourages them to take part in "good old-fashioned booing" and reminds them that "about one thousand million people watching you. So you remember: One wrong word, one foolish gesture — your whole career could go down in flames." You could have cut the tension with a knife. It's arguable that he was being funny, but it's funny like a doctor telling you "you could have cancer and die tomorrow" during a routine exam.
23 | Robin Williams pretends to be Filipino.
Robin Williams was a comedic genius, but even he would have probably agreed that he missed in the mark in this bit from 1986, when he co-hosted the Oscars with Jane Fonda and Alan Alda. When Fonda offered her congratulations to the people of the Philippines, Williams slipped into some comedic improvisation that was embarrassing even by 80s comedy standards. "Come on down, some of these shoes have never been worn, come on down," he said in a mocking Philippine accent. "You come on down you get two pairs of shoes and one black bra free, come on down."
24 | Steve Martin's confusing Meryl Streep diss.
We personally thought that Steve Martin and Alec Baldwin were hilarious as Oscar co-hosts in 2010, but there was one joke that left us (and the rest of the nation) scratching our heads. After pointing out Meryl Streep in the audience, Martin noted that "Anyone who has ever worked with Meryl Streep always ends up saying the exact same thing: ‘Can that woman act' and ‘What's with all the Hitler memorabilia?'" It made no sense. Did Martin think Streep was in a recent Nazi drama directed by Quentin Tarantino, which was also nominated that year? Streep was nominated for a Julia Child biopic, which had zero Nazis. We're still puzzled by it.
25 | Sarah Silverman feels rejected by James Bond
Sarah Silverman had some grievances to air about James Bond during the 2016 Oscars. While introducing a performance of a nominated Bond theme, she complained that after a fling with the fictional character, she never heard from him again. "Like never, not even a text." The 45-year-old continued her diatribe, reminding the audience that Bond "did sleep with 55 women in 24 movies and most of them tried to kill him afterwards." The bit had some funny moments, but the audience wasn't buying it.
26 | Björk's swan dress
Wait, that was a joke, right? When singer Björk arrived at the 2001 Oscars with what appeared to be an entire swan wrapped around her body, we just assumed she was kidding. Right?!
27 | Motion Picture Academy president tries for a laugh.
When Jack Lemmon hosted the Oscars in 1985, the telecast was short on humor. Gene Allen, the then President of the Motion Picture Academy, tried to pick up the slack with a clumsy attempt at levity (you can catch it at the 5:36 mark). After announcing that the show was being watched by one billion people, he added "You can only appreciate what a billion people look like if you've ever tried to find your car after one of these shows." The only one smiling at that joke was Gene Allen.
28 | Neil Patrick Harris makes cannibalism funny again.
Sometimes jokes need a second draft. That's the only explanation we can think of for Neil Patrick Harris, while hosting the Oscars in 2015, would introduce Reese Witherspoon by calling her "so lovely, you could eat her up with a spoon." There's got to be a better way of saying, "She's so pretty."
29 | Whoopi Goldberg on mudslinging.
After her ex-boyfriend Ted Danson got into so much trouble for doing blackface at her Friars Club Roast, you'd think Whoopi Goldberg would've known better. But while hosting the Oscars in 2002, she made a joke that used blackface as a punchline. When discussing the intense campaigning among Oscar contenders, she said, "So much mud has been thrown this year, all the nominees look black." Ouch!
30 | Emma Thompson wants Jane Austen to know about Uruguay.
Emma Thompson had a lot of things to say when accepting her Adapted Screenplay Oscar for Sense and Sensibility in 1996. Like her intention to visit Jane Austen's grave in Winchester Cathedral "to pay my respects, you know, and to tell her about the grosses." And also to remind her "how big she is in Uruguay." There's a joke that makes sense in there somewhere, Thompson just didn't find it. If you want some more Jane Austen in your life, here are the 40 Books Every Woman Over 40 Should Have on Her Bookshelf.
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