May 9, 2017

Unexpected Moments from Two Decades of Webbys

The Webbys has celebrated over two decades of amazing online work—here are some of the best show moments we never saw coming.

The Webbys has been the Internet’s biggest party going all the way back to 1996. When you get the best of the Internet together in one room, you know it’s gonna be wild.

And a little weird.

Here are some unexpected moments from the last 20 years. Check ‘em out below—and watch the full 21st Annual Webby Awards at!

Unexpected Moments from Two Decades of Webbys

The Webbys has celebrated over two decades of amazing online work—here are some of the best show moments we never saw coming.

Hey! It's the guys from that Google site!

First, let’s throw it back to the 5th Annual Webby Awards in 2000, where Google founders Larry Page and Sergey Brin were honored with the Webby Technical Achievement Award. They rolled up to the red carpet in true Y2k-style, draped in tin foil capes.

When Kim K gave us the Kimoji sneak peek

Last year, Kim Kardashian received the first-ever Webby Break the Internet Award. She also gave us an exclusive preview of her upcoming new Kimoji right on the red carpet. This one’s for the haters.

When Prince blew our minds

In 2016, the world said goodbye to Prince, who nabbed a Webby Lifetime Achievement Award at the 10th Annual Webby Awards as one of the first major artists to release music online. We also remember his epic 5-Word Speech, which still leaves our heads spinning: “Everything you think is true.”

When Eva Chen gave Lena Dunham and Jenni Konner a cupcake

Instagram’s Eva Chen presented Jenni Konner and Lena Dunham with the New Founders of the Year Award at the 20th Annual Webby Awards, and she surprised them with a birthday treat along with their Webby. Cue the birthday song!

Fred Armisen is a punk rocker

Fred Armisen gave an unforgettable performance as British rocker Ian Rubbish at the 18th Annual Webby Awards. He didn’t even need his guitar!

When we solved one of the Internet's greatest mysteries

This one sent the Internet into a bit of a tailspin: Steve Wilhite, the guy who invented the gif, schooled us on the correct pronunciation of his file format at the 17th Annual Webby Awards.

That time Dave Grohl showed up to surprise Pat Quinn, who started the ALS Ice Bucket Challenge

The Ice Bucket Challenge was the largest medical fundraising campaign in history, with participants across the globe—including Dave Grohl, who dropped by the 19th Annual Webby Awards to present a Webby Special Achievement Award to Pat Quinn, the co-founder of the movement.

That time "Putin" stripped onstage

M&C Saatchi won The Webby Award for City & Urban Innovation in Social at the 18th Annual Webby Awards. Accepting the award was… Vladimir Putin?

This is why we don't invite the muppets to dinner

The muppets nabbed a Webby at the 14th Annual Webby Awards. Next time, we’ll make sure they’ve eaten before giving them their statue.

Is that Nick Offerman or..?

Pizza Rat was a viral celebrity in 2015, and host Nick Offerman honored the industrious, slice-munching rodent at the 20th Annual Webby Awards. Isn’t the Internet just wonderful?

That time OK Go's drummer got into a staring contest with a Muppet

Shortly after eating his Webby, Animal challenged OK Go’s drummer, Dan Konopka (Danimal) to a staring contest backstage. Things got heated, money changed hands, and Dan will have to use eyedrops for the rest of his life. Probably.

The beginning of geek-chic

Daniel Radcliffe introduced legendary Vogue Editor-in-Chief Anna Wintour, who accepted the Webby People’s Voice Award for Best Fashion Website at the 15th Annual Webby Awards—and gave sartorial inspiration to geeks everywhere.

See you on the dance floor

Amy Poehler won Best Actress at the 14th Annual Webby Awards. And in her 5-Word Speech, she called out fellow winners PS 22 Chorus for a dance party.

You owe your digital life to this man

Hey, ever heard of Vint Cerf? Oh no big deal, he’s just the INVENTOR of the architecture of the Internet. He won a Lifetime Achievement Award at the 14th Annual Webby Awards, but he deserves all the awards for making the whole Internet possible. Just think: Without Vint, there would be no pizza rat, no Ice Bucket Challenge, and *gasp* no Webbys!

The full 21st Annual Webby Awards, featuring Solange, Gillian Anderson, Steve Buscemi, David Duchovny, Jenna Wortham, Wesley Morris, the Women’s March, and more is now available to watch! Check it out at