It started with a little marital feedback.

When Charles Kuykendoll decided to cook oxtail for his wife, Shireen, one pandemic evening, he made it the only way he knew how — the way his Chicago-raised, Black American upbringing taught him. She ate it, said it was good. And then she asked if she could offer some notes. Antiguan and Jamaican by heritage, she gently pointed out that what he'd made wasn't quite the oxtail she grew up with. Kuykendoll, a self-described really, really, really good cook, didn't take offense. Instead, he took out his phone.

He called up Caribbean friends, absorbed their techniques, pulled the best from every recipe, and landed on something he felt confident calling his own. One thing led to another, and in May 2024, what started as a casual backyard competition at his house drew 200 people — far more than his square footage was ever meant to hold.

One viral moment, one chance encounter at Art Basel, and one sold-out Los Angeles event later (2,000 attendees, a $2,500 prize, and a $2,500 donation to a food insecurity organization), the Oxtail Off has become something much bigger than a cookout. Now, in 2026, it's a five-city U.S. tour — a Carnival-infused, diaspora-celebrating food competition that's part HBCU homecoming, part family reunion, part culinary showcase. Kuykendoll brought his deep background in event production (including building and selling Harlem-born party brand RnB House Party to Blavity) to build something truly special.

He spoke with EatOkra about the dish that started it all, what it means to unite the diaspora around a plate, and why the give-back is what he's most proud of.

On how the Oxtail Off actually began

"During the pandemic, my wife and I were bored, and I decided I wanted to make oxtail for dinner one night, but I made it the way that I historically knew how to make it — my mom's way, which is like a barbecue baked sauce, because we're Black Americans as the Caribbean folks call us. I'm a guy from Chicago, the Midwest. She ate it. She's like, 'Oh, this is good.' But then: 'Can I give you some feedback?'

I started calling around to my friends who were good cooks, who were Caribbean — 'Yo, what y'all putting on oxtail?' I learned a lot about butter beans, all the different ways of making it a more Caribbean style. I pulled all of the great flavors from their recipes and made my own. So I thought I made the best oxtail.

Everybody's like, 'Nah,' because everybody thinks they're the best cook. And it got to a point that we were showing each other so much that I was like, 'No, we need to actually do this.'"

On the first backyard competition and how quickly things escalated

"I planned the Oxtail Off at my house — it was like a kickback food competition, Memorial Day Sunday in 2024. We only invited close friends. The five or six close friends I was planning on competing against — we had some friends who were Colombian, Dominican, African. They were like, 'We all make oxtail, we just call it something different.' We ended up with 11 chefs from all across the diaspora, and about 200 people that showed up to my house. My house was not big enough for 200 people...

A lot of my friends are influencers, and people just saw on social this oxtail cook-off thing happening at somebody's house. People were like, 'Yo, can I pull up?' — everyone knows a viral moment.

I ended up going to Art Basel in Miami in December, and I'm walking down the street and somebody comes up to me — 'You're the Oxtail Off guy.' I was like, 'Whoa. All right, this is something special.'"

On what his professional background brought to the build

"Having started my first business, RnB House Party, and building that to scale to ultimately sell it to Blavity — and my two years at Blavity, in which I was assisting with Afro Tech and understood production to a large extent, understood stage scripting and really the arc of anything — that was a good training ground.

I was no longer trying to be the club guy, because my interests had changed from when I started RnB House Party in my 20s. Something that really aligns with my passions, what I do for enjoyment, is cook. That is therapy for me.

The business side came through immediately — the minute I did it at my house, we had cups. We incorporated the business, we locked up Oxtail Off on social, we did all of that so far in advance before ever going to market, because we understood how to actually build a business."

On what makes the Oxtail Off feel like more than a food competition

"We're not trying to necessarily give people a taste of what they already experience and see. We're trying to give them a taste of Carnival, which a lot of people don't get a chance to go down to. So we're having moko jumbies on site — the walkers on stilts. We're going to have ladies dressed in mas costumes, playing mas.

We're partnering with the Tourism Board of Barbados, and every single winning chef gets a free trip to Crop Over — to play mas and go experience that authentically. We're trying to be that bridge between what's happening in the Caribbean and getting Black Americans, or Americans in general, to be interested and continue to go down there."

On what oxtail represents as a through-line for the diaspora

"Oxtail being such a delicacy now — being that it was once the forgotten food — just speaks to how us as Black people are able to take something and make it so special. It's happened time and time again in our history. That's just one of our superpowers, just celebrating the uniqueness of our culture.

Hopefully new people are going to be able to experience it and understand why so many people are excited about it."

On what he's most proud of heading into the tour

"Our vision is to amplify small businesses. Some of the food vendors are pop-ups, some are famous restaurants in the region, but a lot of them are mom-and-pop restaurants. We hope one or two to ten to twenty people get to taste their food and become consistent customers.

The thing I'm most proud of is the give back. We're giving $20,000 across this tour in these different cities. At this stage in my life, that, to me, is what's most important.

I'm getting such great feedback — people are like, 'You mixed the HBCU homecoming with Carnival with a family reunion.' We wanted to scale this ourselves, be full owners in it. I have such a strong vision — me and the team — as to what this can become."

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