Nominees Announced, Vote until April 18th
28th Annual Webby Awards May 9, 2023

The Most Iconic Webbys Moments of All Time

From Pizza Rat to Norah Jones to a surprise visit from Prince, look back on twenty-seven years worth of wild and weird moments from 28 years of the Webby Awards.

When the first Webby Awards was held in 1998, the show—much like the industry itself—looked very different. There were fewer categories, with each recognizing websites. This year’s Webby Awards will recognize the industry’s best creatives across digital advertising and marketing, podcasting, social, online video, gaming, immersive and mixed reality, Web3, and more. All a testament to how far online innovation has come and how far it can go. 

Ahead of the 28th Annual Webby Awards, we’ve highlighted our favorite moments throughout 28 years of the Webby Awards—unexpected moments, memorable presentations, musical performances, and the most iconic 5-Word Speeches. 

From sneak peeks with Kim Kardashian to music by Norah Jones to a surprise proposal, look back on 28 years worth of wild and weird moments at the Webby Awards. Our Extended Deadline is your last chance to take the Webby stage. Enter before Friday, February 9th

The Most Iconic Webby Moments of All Time

From Pizza Rat to Norah Jones to a surprise visit from Prince, look back on twenty-seven years worth of wild and weird moments from 28 years of the Webby Awards.

5th Webbys (2000): Google Founders in the Wild

First up in our list is the 5th Annual Webby Awards in 2000. Google founders Larry Page and Sergey Brin received a Webby Award for Technical Achievement for their search engine, which is a bit of an understatement today. They strolled on the Webbys Red Carpet, donning foil capes, to talk about their dreams of running a successful company.

10th Webbys (2006): Prince Questioned What We Know

Webby Lifetime Achievement Winner and late artist Prince delivered one of the best 5-Word Speeches made at The Webby Awards: “Everything you think is true.” He then closed out the ceremony with a performance, breaking his guitar at the end.


11th Webbys (2007): A Special Moment for Ziggy Stardust

David Bowie, affectionately known by his stage personas “Ziggy Stardust” and “The Thin White Duke,” received the 2007 Webby Lifetime Achievement Award. The visionary artist, his life’s work and the Internet were intrinsically tied. From launching BowieNet, his seminal Internet service provider, to encouraging fans to remix his music to BowieArt, an innovative website that connected visual artists with art collectors worldwide. Watch the iconic himself accept his honor.  


12th Webbys (2008): Stephen Colbert Practiced Self-love

Sometimes the best thing to do is focus on yourself. The Late Show host Stephen Colbert did just that, as he accepted the Webby Person of the Year Award. His 5-Word Speech is the epitome of self-love and a healthy dose of self-obsession: “Me, me, me, me, me!!!”


13th Webbys (2009): An Ode to The Muppets’ Beaker

At the 13th Annual Webby Awards, Beaker of The Muppets accepted a 2009 Webby People’s Voice Award for “Ode to Joy,” their special music video.


14th Webbys (2010): P5 22 Chorus Keeps it Cute

The PS22 Chorus, directed by educator Gregg Breinberg, is a public elementary school chorus from PS 22 in Graniteville, Staten Island, New York. They accepted the Webby Artist of the Year Award for gaining more than 17,000,000 YouTube views, and countless fans, including some of the most respected artists of the time.


15th Webbys (2011): Norah Jones Pays Tribute to Johnny Cash

Incomparable singer-songwriter Norah Jones performed “Ain’t No Grave” at the 15th Annual Webby Awards, as part of The Johnny Cash Project. The project was a collaborative and interactive music video, led by immersive artist and entrepreneurs Chris Milk and Aaron Koblin. 


15th Webbys (2011): Honoring Activism from Egypt to the World

Egyptian filmmakers Mohamed Diab and Amr Salama accepted a Webby Special Achievement Award on behalf of the people of Egypt for leveraging the power of social media to spark a revolution in Egypt. Their actions would go on to create a blueprint for activists around the world — from the movement for Black Lives to protesters in Peru to women and allies in Iran.


16th Webbys (2012): The Incomparable Björk wins Artist of the Year

No one does Björk like Björk. Interactive media artist Scott Snibbe presented the visionary with the 2012 Webby Artist of the Year Award for her seventh studio album Biophilia, the world’s first app album. The project was released with a series of apps and workshops, exploring the link between music, nature and technology.


17th Webbys (2013): Steve Wilhite Settled the Internet’s Greatest Debate

This one really sent the Internet into a tailspin: Steve Wilhite, late inventor of the GIF finally settled the debate on the correct pronunciation of his file format. Officially, “It’s pronounced “JIF” not “GIF.”


18th Webbys (2014): Comedian Fred Armisen Transforms into Ian Rubbish

Actor, comedian and Portlandia creator Fred Armisen performed as Ian Rubbish, his alter-ego. His fake Sex Pistols-like band originally performed in Saturday Night Live’sHistory of Punk” sketch, but the bit was so good, Armisen went on to release a real EP.


19th Webbys (2015): The Foo Fighters Surprised the Creator of the ALS Ice Bucket Challenge

Co-founded by Pat Quinn, the ALS Ice Bucket Challenge was the largest medical fundraising campaign at this time on the Internet. It raised $115 million for the national office of The ALS Association in 2014 and inspired participation across the world, including from celebrities like Oprah, Bill Gates, Selena Gomez, Kim Kardashian, and Dave Grohl of the Foo Fighters. The latter showed up to surprise Quinn in a special moment on the Webbys stage. 


20th Webbys (2016): Kim Kardashian Gave Us a Preview of the Kimoji App

There was a time when celebrity apps were all the rage. From Shakira to to Ellen Degeneres to Selena Gomez, there was an app for everything. Before receiving the Break the Internet Award at the 20th Webbys, Kim Kardashian gave us an exclusive preview of her upcoming new Kimoji on the red carpet. This one’s a message to the haters.


21st Webbys (2017): Solange Sang the Sweetest Five Words

Artist and filmmaker Kara Walker presented Solange with the 2017 Webby Artist of the Year Award for the creation of Saint Heron, her collective, collaborative platform and store for artists of color. While accepting she sang her 5-Word Speech, “I got five on it.”


22nd Webbys (2018): Host Amber Ruffin Explains Blockchain, in Song

Amber Ruffin, comedian, writer and host of the 22nd Annual Webbys, gave our audience a quick lesson on blockchain technology—in song, while dressed as Sheila E. The moment was too good to miss.


23rd Webbys (2019): Jesse Williams Embraced the Fear

Gritty, the Philadelphia Flyers’ beloved mascot made a surprise visit at the 23rd Annual Webby Awards. In a strange moment filled with confetti, Gritty accepted his Webby Award for his true display of exceptional character.


24th Webbys (2020): Miley Cyrus Spread Positivity During the Pandemic

During the height of the pandemic, Miley Cyrus launched her Instagram Live show, Bright Minded: Live with Miley. The show featured positive conversations about which tools celebrities used to maintain healthy minds, bodies and spirits during stay-at-home orders. Her 5-Word Speech was a positive affirmation for us all: “Stay lit in dark times!”


26th Webbys (2022): Megan Thee Stallion Speaks Truth to Power

Megan Thee Stallion, the 2022 Webby Artist of the Year, took the Webby stage with grace and used her onstage moment to plug a critical call to action. She demanded bodily autonomy in five simple words: “Take bans off our bodies!”


27th Webbys (2023): Shigetaka Kurita Delivered the First-Ever Wordless 5-Word-Speech

Digital pioneer Shigetaka Kurita was honored with a Webby Lifetime Achievement Award for creating emojis in 1997. He was nothing but smiles onstage and delivered the first-ever all-emoji 5-Word Speech: 😊🤝🌎🤝😊


Friday, Feb 9th is Your Last Chance to Enter the 28th Annual Webby Awards

When you enter, you get the chance to celebrate your victory at the Internet’s biggest party in New York City and immortalize your win with a 5-Word acceptance speech. Five words might not seem like a lot, but the speeches become Internet icons—Webby Awards clips have received over 14 million views on YouTube!

To shine a global spotlight on your creativity at the Internet’s biggest night, enter before the Extended Deadline on Friday, February 9th—your last chance to enter!