Caitlin has taken over the New York City comedy scene, regularly performing at the world-renowned Comedy Cellar, New York Comedy Club, and Gotham Comedy Club, among others. “I love including the audience in my jokes,” Caitlin tells Tudum. “I want each show to seem like a stand alone night and the goal is for the audience to leave with an inside joke they just can’t quite explain to people who weren’t there.” She’s not new to the world of TV, appearing on The Tonight Show Starring Jimmy Fallon, The Late Show with Stephen Colbert, The Late Late Show with James Corden, After Midnight, and more. Her debut album, Dirty Bird, hit number one on the comedy charts. 

In Usama’s hometown of Plano, Texas, there was this thing called the Snow Dance. “If you wanted school to get snowed out, you would wear your clothes inside out and do a dance,” he tells Tudum. He rose to the challenge and filmed himself dancing to the Bollywood tune of “It’s the Time to Disco” then posted it on Facebook. To his peers’ joy, it snowed the next day. “The cutest girl in school was like, ‘That video was really funnyyyyy,’ ” he says, recalling the lilt. “I was like ‘This is my life now, whatever I need to do to get girls to say ‘funnyyyyy’ like that, I will devote my life to it.” And that is why Usama became a comedian. In 2024, he made his late-night debut on The Late Show with Stephen Colbert, and in 2025, he released his first half-hour comedy special with Don’t Tell Comedy. He recently wrapped his first national headlining tour and has also opened for Hasan Minhaj and Morgan Jay. Outside of telling jokes, he’s a writer with credits on Inventing Anna, Survival of the Thickest, And Just Like That, and more. 

In his junior year of high school, Ron’s swim teammates let him in on a little secret: he’s funny af. “I like to think that I put a silly flair on serious things,” he tells Tudum. Since 11th grade, he’s fine-tuned his comedy chops by watching his favorite comics. “I learned how to pace myself and squeeze all I can out of each topic,” he says. Handpicked by Bill Burr to perform on Comedy Central’s stand-up series The Ringers, Ron is now a paid regular at world-famous The Comedy Store in Hollywood. After considering what Ron would name his Netflix special if he were to win, he landed on Escalate. “Because I’d be finally going up!”  

I first realized I was funny when I could laugh my way out of trouble,” Reg tells Tudum, crediting his mom as the first person to tell him he was funny. Drawn toward comedians who fearlessly approach taboo topics, Reg also likes comedy that takes a personal angle or experience and finds a way to make it relatable through the jokes. Perhaps that’s why his comedy always contains depth. “For as funny or wild as I get on stage, my material always has heart,” he says. A seasoned comedian who has toured with Amanda Seales (Insecure) and Chris Redd (Saturday Night Live), Reg also produces his own comedy show, Productively Stoned.

Winston isn’t in rural Virginia anymore. The comedian has toured the country and opened for Fortune Feimster and Derrick Stroup, showcasing his southern charm, surprising vulnerability, and edgy wit. “I think I have a way of speaking about some very touchy subjects in a way that is palatable to everyone,” he tells Tudum. “Whether you agree with me or not, you are probably going to laugh.” Winston realized he had a knack for comedy when his parents would tell him, “Quit being funny and making jokes” during church. But his comedy career kicked off at the Funny Bone in Richmond, Virginia. Now, Winston is a regular at the Comedy Cellar, has been featured on Don’t Tell Comedy, and self-produced his award-winning special Grieving Productively.

“I realized I was funny in high school because of my girlfriends,” Andrea tells Tudum. The crew would laugh for hours to the point of a bathroom emergency. “None of them peed their pants, but I peed my own pants,” she says. “It was proper proof that I was funny.” Andrea’s comedy may not seem as “structured” as other comics’ in the competition, but that’s by design. “I don’t write towards a punchline, but I try to let them come out naturally,” she says. “My rhythm is a bit unorthodox, but it works for me.” She gained recognition in the comedy scene after winning Comedy Album of the Year in 2021 at the Juno Awards for her solo album Grandma's Girl. Currently based in Los Angeles, Andrea recently made her late-night TV debut on The Late Late Show with James Corden. 

Like many comics before him, Steve draws on personal experiences for his material. “Stories connect to people’s souls,” he tells Tudum. Currently touring with David Cross and Ali Wong, and fresh off a three-year run opening for Bert Kreischer, he’s ready for a solo show. If he were to win the competition and earn the prize of a Netflix special, he’d call it Everything, “Because it’s everything I’ve done so far in my career.” When he’s at home in LA, you might find him performing at The Comedy Store and Hollywood Improv, or munching on street tacos. And no, not Taco Bell. “Get better food from a real person,” he says.

At first, it’s hard to say if Olivia’s deadpan delivery is simply a character or her own neurosis. “I try just to be myself 100 percent of the time,” Olivia tells Tudum. Studying her favorite comics taught her the importance of writing, writing, and more writing. “And love the crowd, they are in the room with you too,” she says. As an audience member, she enjoys seeing comedians be true to themselves. Part of being herself is owning unpopular opinions, like admitting she hates the beach. “I don’t even own a swimsuit,” she says. After majoring in theater in New York, the comedian and actress considers all her sets “performance pieces.” This mindset led to her being named a 2025 New Face at the Just For Laughs comedy festival and invited to perform on The Tonight Show Starring Jimmy Fallon and Kill Tony.

Hailing from Los Angeles, Felicia’s brought her authentic and relatable energy to the stage at iconic venues across the country, including The Comedy Store and The Laugh Factory. She can’t recall the specific moment she realized she had a knack for comedy, but it’s been for quite sometime. She tells Tudum, “I’ve been funny as long as I can remember, but I don’t have a good memory.” While Felicia calls her brand of comedy “different,” she also draws one aspect of inspiration from her favorite comedians. “Delusion. All the greats are delusional, and I want to be just like them.”

Eva has always known she’s funny, but it was still nice to win the “funniest” superlative in high school. In 2025, she performed at the Netflix is a Joke Festival with a set that highlighted her time working in foster care and a homeless shelter in Brooklyn — despite the heavy topics, it was still funny AF. “There’s only one Eva,” she tells Tudum. “My style is uniquely me; no one else can tell my story.” Outside the comedy festival circuit, Eva has been featured on The Wendy Williams Show and BET, and regularly produces comedy shows across New York City. She has also participated in an art therapy program at Rikers Island. 

We can all thank Ray’s 4th-grade teacher, Mrs. Brin, for sending him on the path to comedy after applauding his Hannah Montana impression. Named one of Vulture’s 2025 Comedians You Should and Will Know, Ray plans on touring nationally this year. Since his elementary school days, he’s learned a lot from his stand-up idols. “I take different things from different people,” Ray tells Tudum. “I love how much fun Geoffrey Asmus is having and how much the audience is bought into him just clearly fucking around.” Ray learned how to command a room from Godfrey and Laurie Kilmartin. Ali Siddiq taught Ray the art of good storytelling. And from Comedian CP? “I just love how silly his bits are.” Ray loves a silly bit himself and has gone viral for the “Chipotle Bean Scheme” featured on Netflix is a Joke’s “Introducing …” series.