Gen Z Ruled the Internet at the 2025 Webby Awards — And I Had the Best Seat in the House

The 29th Annual Webby Awards turned Cipriani Wall Street into a glittering temple of Internet excellence last night, and if there was one thing clear from the start, it was this: Gen Z isn’t just part of the culture — they’re leading it. With a star-studded room full of creators, disruptors, and digital pioneers, the night felt like a high-speed tour through the best (and weirdest) corners of the Internet — and I had the surreal privilege of sitting just one table over from the people who made it all happen.

Hosted by the irreverent and razor-sharp Ilana Glazer, the Webby Awards celebrated everything that makes the web a glorious mess — creativity, chaos, and cultural impact. From viral icons to visionary activists, the five-word speeches (a Webby signature) hit hard, sparked laughter, and reminded us of the power of saying a lot with a little.

But no group owned the night quite like Gen Z.

Jake Shane, known for his whip-smart comedy and endearingly neurotic TikToks, won the Webby for Comedy, Individual Creator. His five words? “I want to say more.” And honestly, same. Sitting near Shane as he beamed, surrounded by peers and fans, it was obvious: he’s not just a TikTok star. He’s the face of a generation redefining what comedy even means in 2025.

Jools Lebron — the viral sensation behind the now-iconic “very demure, very mindful” moment — took home the Crush the Internet Award, presented by Peppermint. Her impact was so massive that “demure” became Dictionary.com’s Word of the Year. Jools’ win felt like a coronation of the new influencer era: thoughtful, hilarious, and utterly Gen Z. Watching her deliver her speech from just a few feet away (“Very demure, very successful, period.”) was like watching history meme-ifest itself.

Amelia Dimoldenberg, the mastermind behind Chicken Shop Date, received a Special Achievement Award for reinventing celebrity interviews. With her awkward charm and deadpan wit, she’s become a go-to for stars and stans alike. Her speech? “Don’t wait. Make it yourself.” If there’s a Gen Z creative motto, that’s it.

Even veteran actors like Walton Goggins, who won Best Actor for roles in Fallout, White Lotus, and The Righteous Gemstones, gave the stage over to a new energy. Introduced by Justin Theroux and met with huge applause, Goggins grounded the evening with a humble, perfect five-word mic drop: “If it happens, be grateful.”

I watched him clink glasses with creators half his age who’ve racked up billions of views. That collision of worlds — prestige actors beside meme-makers, social activists beside streamers — is what makes the Webby Awards electric. It’s not just a show. It’s a timeline made tangible.

The room buzzed with real crossover: Sean Evans handing Amelia her award; Congresswoman Jasmine Crockett delivering a fiery, unforgettable “Only organized outrage overcomes oppression”; Chris Klemens introducing a stage full of creators including Caleb Simpson, The Rizzler, and Maddie Lymburner; and Ice-T presenting Entrepreneur of the Year to none other than Snoop Dogg.

And all night long, Gen Z was front and center — not just for the camera, but in every side-eye, every shoutout and every moment. We weren’t just watching the Webby Awards. We were watching the Internet in motion, shaped by the people who understand it best.

As I sat surrounded by the very stars dominating our feeds — sharing air with Jools, Jake, and Amelia — I realized this wasn’t just a recognition of the year’s best. It was a glimpse into the future. And from where I was sitting, it looks like the kids are more than alright — they’re all good.

For a full list of winners and more unforgettable five-word speeches, visit webbyawards.com or search #Webbys across socials.