More than 1,000 of the Internet’s most creative voices gathered in New York City for the 2nd Annual Webby Creator Weekend presented by Adobe. The two-day, invite-only event celebrated Webby-recognized creators, bringing together a curated mix of brands, platforms, and digital talent to explore the future of online creativity with the people actively shaping it.

High above Manhattan at Elsie Rooftop, creators, platforms, and industry leaders gathered to connect, collaborate, and trade ideas on building work with lasting cultural impact beyond the trend cycle.

Following opening remarks from Webby GM Nick Borenstein, Day 1 opened with a conversation on the future of podcasting in partnership with Patreon. Creators Chris Klemens, and Julia Hava unpacked how direct-to-fan relationships are reshaping audience growth, offering a candid look at what it means to build community outside the algorithm and create content on your own terms.

The afternoon continued with a keynote from viral comedy duo Grant Gibbs and Ashley Gill, better known online as “A Twink and a Redhead.” The pair reflected on turning deeply online humour into a breakout entertainment brand, sharing the creative instincts behind their Internet-famous sketches and the realities of sustaining momentum online today. The conversation ended with a live performance including their viral “Disney Adult” song, as attendees sang and danced along across the rooftop.

The conversation continued with “Create Without Limits: How AI Is Expanding Who Creates,” presented in partnership with Adobe featuring Brandon Baum, Valerie Zhang, and Pablo Rochat. Creators and industry leaders explored how generative AI is reshaping the creative process, from accelerating ideation to lowering barriers for emerging talent, while reflecting on the importance of maintaining a distinct creative voice in an increasingly AI-powered landscape.

Throughout the weekend, Adobe also brought the conversation to life through an interactive generative AI activation powered by Firefly, where attendees transformed their portraits into personalised “love letters” to New York City. The experience quickly became a crowd favourite, with creators lining up to remix, experiment, and share their AI-generated visuals across social. Guided by Adobe ambassadors at on-site editing stations, guests explored how intuitive AI-powered creative tools can help turn ideas into polished, shareable content in real time.

The day continued with “Built in Public: Scaling Everyday Content,” presented in partnership with Snap featuring Kalita Hon, Sofi Ibrahim and Christian Crosby, moderated by Nick Kosir. Creators shared how seemingly ordinary moments can become compelling, repeatable content formats when paired with strong storytelling instincts and an authentic point of view. The conversation unpacked the nuances of pacing, audience connection, and creating content that feels immediate and personal, offering an inside look at how creators turn everyday experiences into communities that keep audiences coming back in real time.

Day 2

The second day started with a powerful conversation on how Black creators continue to shape Internet culture, drive global trends, and influence the way communities engage online. Moderated by Webby Head of Brand Strategy Jordana Jarrett,  creators Anania, Allyiah Gainer, and Achieng Agutu.  joined Vanessa Mbonu, the Digital Director of the NAACP to discuss the realities of visibility, ownership, and cultural impact in today’s rapidly evolving digital landscape. The conversation offered an honest look at the influence Black creators hold online, while exploring the challenges and opportunities that come with building culture in real time.

The afternoon continued with “Almost Famous: Inside the Celebrity Lookalike Phenomenon,” where Webby Winner Anthony Po unpacked how a Timothée Chalamet lookalike contest unexpectedly became one of the Internet’s most viral cultural moments. Joined by Christian Conti and Zander Dueve, two standout personalities from the now-iconic competition, the conversation explored why lookalike culture resonates so strongly online and how spontaneous, community-driven moments can quickly evolve into global Internet phenomena.

Later, “Campaigns to Community: Creator Partnerships Built to Last,” presented in partnership with We Are Social,  brought together creators Serena Kerrigan, Miranda Sanchez, Loco Ninja, and Nick Kosir, moderated by Krisztina Virag for a conversation on the future of creator-brand collaboration. The discussion explored the growing shift away from one-off sponsorships in favour of long-term partnerships rooted in authenticity, creative freedom, and shared audience trust, highlighting how sustainable collaborations are reshaping the creator economy for both brands and talent alike.

Throughout the weekend, The Anthem Awards hosted the Anthem Lounge in partnership with The Strangers Project, creating a reflective space centred around storytelling, connection, and shared human experience. Inspired by The Strangers Project’s mission to celebrate the stories we carry and the strangers we encounter every day, attendees were invited to anonymously share personal thoughts, experiences, and reflections throughout the activation. The lounge quickly became one of the weekend’s most-loved experiences, drawing creators in for quiet moments of honesty, vulnerability, and connection amid the energy of Creator Weekend.

The weekend wrapped with “Live From New York: The New Late Night,” moderated by Webby Awards General Manager Nick Borenstein, exploring how creators are reinventing the interview format for the Internet generation. NYC-based hosts Tiffany Baira, Michelladonna, and Aidan Wall reflected on building interview formats that feel more spontaneous, personal, and culturally connected, from conversations on city sidewalks to inside local shops and neighbourhood staples. The panel highlighted how audiences are gravitating toward raw, unscripted interactions online, signalling a shift away from traditional late-night formats toward creator-led conversations that feel immediate, intimate, and deeply native to the Internet.

The Webby Newsstand pop-up experience became a major crowd favourite, with attendees lining up across both days to discover products from Rare Beauty, KraveBeauty, Dossier, JacknJellify, KIND Snacks, and more. Additional support from community partners Nut Factory, Honeydept, Sourmilk, and Bezi helped bring the weekend to life through curated products, immersive experiences, and creator-focused moments across the event.

From bold streetwear looks to statement vintage pieces and rooftop-ready fits, creators showed up with the same individuality and creativity that defines their work online. Across both days, the energy was unmistakable, with conversations spilling across the rooftop, creators collaborating in real time, and communities that usually exist online coming together face-to-face. The combination of standout talent, genuine connection, and Internet culture made the 2nd Annual Webby Creator Weekend feel less like an industry event and more like the ultimate gathering for the people shaping what’s next online.

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Follow @thewebbyawards on Instagram, X, TikTok, YouTube and LinkedIn to see the best moments from the weekend. You can view more photos from the event here