The Funniest Oscar Presentations Ever

Maya Rudolph and Kristen Wiig, 2020

Rudolph and Wiig hammed it up during their presentation, pretending to be outraged, then getting choked up at the concept of “production design.” Why? Because there were “a lot of directors” in the audience and they wanted them to know they do more than comedy…

Will Ferrell and Steve Carell, 2006

Ferrell and Carell presented the award for Best Make-up with deadpan seriousness – but with faces caked in a thick layer of garish compounds and fake eyelashes.

Pee-Wee Herman, 1988

In what was arguably a high point for the Academy, and the medium of television in general, Paul Reubens, in character as Pee-Wee Herman, took the stage but was attacked by the ED-209 killer robot – and then promptly saved by Robocop. At the end of which, Reubens quipped: “I’ll be right back to present the Oscar as soon as I change out of my pants.”

Rodney Dangerfield, 1987

Dangerfield showed up, and flat-out did his act in the middle of the Academy Awards. He even added one-liners to the clips of nominees for Best Make-up.

Carrie Fisher and Martin Short, 1989

Carrie Fisher is horrified to discover that co-presenter Martin Short is wearing the same outfit as her – the joke isn’t so much that man is wearing a dress, but more that Short is so desperately hungry for attention that he would deliberately copy Fisher’s ensemble. 

Eddie Murphy, 1988

Eddie Murphy presented the Best Picture Oscar to The Last Emperor – but first, he riffed about how he initially turned down the offer to do the show because the Academy doesn’t recognize Black performers. While not exactly hilarious, the fact that Murphy used his comedic charms to go off-script and shine a light on the systemic rot of the Academy made this a truly memorable moment. 

Ben Stiller, 2006 & 2010

Further proving that the Best Make-up category is fertile ground for comedy bits, Ben Stiller showed up in full Na’vi-face – despite the fact that Avatar wasn’t nominated. 

Jack Black, Will Ferrell, and John C. Reilly, 2007

In an elaborate musical number in 2007, Will Ferrell and Jack Black sang about how sad it is to be a comedian at the Oscars, with Ferrell lamenting that he never even got to have dinner with Jeremy Irons. Then they croon about physically attacking the nominees – Black threatens to assault Peter O’Toole with his Nickelodeon award –  before John C. Reilly breaks it up, also through song.

If only Reilly had been in the audience and equipped with a microphone last year …

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