Reporter Don Lemon caught in a moment of laughter with interviewer Joshua Dudley
Joshua Dudley
This year marks the 30th anniversary of the Webby Awards. Since 1996 they have been celebrating internet excellence and 5-word acceptance speeches and have grown to encompass nearly everything on the internet - audio, video, games, social media, commercials, games, and more. The winners came dressed to impress and were eager to promote their projects and bask in the glory of being declared the best of the internet.
Here are some highlights and long form transcripts of my red carpet interviews at the Webbys this year.
Comedian Ali Saddiq known for his comedy stylings about family and fatherhood won three Webby Awards for his comedy special Rugged and I asked him about it.
Tell us about Rugged, and what’s the difference between it and your previous special My Two Sons, and how did that lead into that?
Ali Saddiq: My Two Sons was a great account of me being a father to a older son- versus my newer son, and then Rugged is me being a father and making mistakes, showing my kids that being vulnerable in front of them and getting them to understand that even though you make mistakes, you just see it through, you know? That's the difference.
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AS: You electrocute yourself one time, I don’t think you’ll do it again.
Grant Gibbs and Ashley Gill collectively known as A Twink and a Redhead won a Webby for Instyle’s ‘The Intern’.
According to the pair they have known each other since 6th grade, been besties ever since and they make fun little sketches and satirical music and are on tour with a musical that they wrote, directed, and produced themselves. They say they are the hottest people on Earth, and multi-hyphenates.
Their biggest inspiration comes from the Lonely Island digital shorts from SNL and the movie that came out of that Popstar: Never Stop Stopping and also Weird Al Yankovic. I told them I saw Weird Al once and he did a costume change for every song, and in response they told me they have costume changes and there might be some wardrobe malfunctions on tour as well. Their producer is the icon Drew Lewis and they accepted a Webby for Instyle’s “The Intern” series. They were excited and nervous to be accepting an award for a whole team and Ashley said she heard a rumor that the guy that played President Fitz on Scandal was gonna be in the room, "and I’m definitely curious to lay eyes on him”, “And Shonda Rhimes,” Gibbs added.
Anthony Dimierei and Debbi Saslaw are part of a video production team called Melted Solid and they won two Webbys for their work on now NYC mayor Zohran Mamdani’s Halaflation campaign.
They told me they were also responsible for him riding around town on buses and trains and they even recommended he take the polar plunge. Which they are very sorry for. We call him the Mayor they said. In Halalflation, Mamdani was talking to Halal Cart owners about the price of street food underscoring how much he cared about issues that small business owners face. Debbi says that put Mamdani on the map, “We’ve been working in the content space for ten years and decided to bring it to politics and now we’ve unleashed the beast!” They also helped Analilia Mejia get elected to Congress in New Jersey and just last week filmed Elizabeth Warren and Brad Lander
Pooja Tripathi is the creator and alongside Darryl Gene Daughtry Jr they are the stars of Brooklyn Coffee Shop, a popular YouTube Show that won the Webby for Video & Film: Comedy.
At the Webby Awards red carpet, the comedy duo behind Brooklyn Coffee Shop, Pooja and DJ, celebrated their win with the same "perpetually unimpressed" energy that has made their series a hit. Portraying hipster baristas who are "very, very rude to our customers," they explained that their characters don't actually like people or want more business. "We charge them for everything. We recharge them," Pooja joked, adding that they always expect a tip despite the fact that customers "rarely get their drink" because the baristas don't actually know how to make them.
In each episode a different guest sometimes played by a celebrity like Kumail Nanjiani or Atsuka Okatsu will walk through the door to get insulted by the pair.
So why do people come in? I asked them. “I think for the vibe,” Pooja told me
It’s a really fun watch, and Pooja and DJ are going to be on my list of comedians on the rise.
Josh Johnson is a current host of The Daily Show, makes weekly content for YouTube, and was the host of the 2026 Webbys.
He revealed his secret to coming up with so many original jokes each week “I just don’t do anything else. That’s really it. Just doing one thing will yield incredible results if you forgo literally everything else."
Josh Johnson: I’d like to be better at chess. Right now I’m pretty bad. And, I'm bad in a way where when I’m playing I don’t know what to do but I know something bad is about to happen, So they'll move their queen, and I'm like, That's not good.
JJ: I'm going to do my best to start it by being funny. That's the hope. That's the idea.
JJ: Oh, huge amount of pressure. Yeah,I just want everyone to have a good time. And then as someone who's not fantastic at throwing parties I want to make sure I serve Webby as best as I can.
JJ: I think the way that we are getting into AI is I don’t know. It’s a bit troubling that everyone is like, oh, I have an app and now I don’t need anyone to support my business. It’s like, well, you still need the employees, you know? So, I think that’s one of the main things that’s taken up a lot of my brain space and just like seeing the developments. It’s all happening so fast. Like, first chatgpts at the top and then DeepSeek and then Claude.
JJ: Which tells me that we as people need to do better. I don’t know if you've noticed people lately, but some of them are pretty bad.
JJ: Yeah. That might be why Claude was nominated and then chosen.
The 2026 Webby Award Winner for best stand up special for her show Father now streaming on Hulu, comedian Atsuko Okatsuka’s comedy centers around her family, specifically her grandma and then her husband
I’ve been following her on Instagram for some time and interviewed her previously for her last special The Intruder, and that’s why I knew that her dear grandmother had been rushed to the emergency room just a day or two before the Webbys, and so I had to ask her about that.
Sorry about your grandmother. I wasn’t even sure you were gonna be here today.
Atsuko Okatsuka: Oh, my gosh. Thank you for asking. Yeah, I was at the emergency room with my grandma yesterday, and she’s got five staples in her head. She's on her way to recovery.
Yeah. I'm so glad to hear that.
AO: And so she said, "You go. You go, girl." I said, "Okay, here I come."
You might be the only comedian I know whose career started because of their grandmother.
AO: Yeah, I mean, you know, all of it is, like, a matriarchal start for all of us, you know? My grandma raised me, and because of that I ate well. I ended up in the US whether I wanted it or not. And then now, you know, I said, "Okay, I gotta go to New York. I gotta do this so that I can pay for that emergency room bill." That’s America. That’s full circle. That’s being an immigrant.
Well, thank you for being an immigrant here tonight. What did you win for?
AO: I won best standup comedy special for Father.
I had a feeling it was for best standup special. The Intruder was great. So how do you change the world so much on a weekly basis?
AO: Well I mean, I guess I’m just kind of an open book, so I’m very honest with, who I am. Yeah. You know, every- you know about my grandma because I tell stories about what’s happening with me, and then other people feel hopefully less alone because of it. They go, "Oh, I went through that with my grandma," or, you know. "I know what it’s like to have to still hustle," and when there’s, like, be- behind the scenes, like, family issues or you’re dealing with or emergencies, and that’s why I became a comedian, because I want other people to feel good, and even get to escape a little bit from what they’re going through, too.
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And would you believe her 5 word speech at the end of the show was: Formerly undocumented immigrant, current winner.
Veteran newsman Don Lemon won a 2026 Webby Award for The Don Lemon Show and my interview with him was so gripping about the responsibility of journalism that the whole thing needs to be read.
Don Lemon: The most dangerous man in news?
DL: No, I'm not afraid. Why should I be afraid?
DL: Okay.
DL: I got arrested one time. And there were many journalists who came before me who were arrested for not revealing their sources, for going into places where the news is. So look right now this is a pivotal time for us to fight for the First Amendment and freedom of speech, and we've all been here before.
We’ve all been through fascist regimes. We've all been through the civil rights movement. And some of the people who we admire the most in the world have been arrested-and got into good trouble, like John Lewis and Dr. King and Jesus.
DL: Because I know what I’m doing is right, and I operate with a moral compass, and I operate with empathy and humility. And as long as you remain in gratitude and as long as you remember that, I think you’re good. What I am keenly aware of is that I work for not just the American people, but the people of the world. So I am a servant of those folks. What this administration does not realize is that they’re public servants. They think that the American people work for them, and in many ways we are, because we're making them richer.
DL: I will say that I have my strong work ethic. The support that I have behind me. But more than anything, um, I serve a person. I serve a person, meaning a person who walked the earth before. And a God that keeps, and protects me. And I know that I’m gonna be all right, and I know that whenever you go through whatever it is, there's something in it that is positive that's going to come out the other side, as long as you're doing the right thing.
Probably not coincidentally, Don’s 5 word acceptance speech later that night was “A free press is essential.”
Tiff Baira, the official red carpet correspondent for the 30th annual Webby Awards is the creator and host of Street Hearts, a popular TikTok show that sets up strangers on the street with blind dates.
She brought a "natural" and infectious energy to the red carpet in her second year hosting for the event and I got to see both her interviews and her warm ups in person and she brought exactly the right amount of energy for a fast paced event like this one.
She said the positive energy gives you a lot of hope and that you never know what someone’s going through which is why we need each other and why we have to keep showing up doing interviews and making content because we never know what’s going on.
She attributed a lot of sleep, working out and the love of friends and family as to how she stays so positive. “It’s contagious”, she said. "Once one person believes in you, then everyone does.
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And as the lights dim on yet another Webbys red carpet, the bright lights of the best of the internet keeps on going and people with dreams, and big hearts, and something they have to say keep saying the things that keep needing to be said.
Catch ya next time on the Webby’s red carpet!
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