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Uriel J Winfree III does not believe in limiting himself in any way. He also refuses to be judged by society’s conventions and it shows in his life and his art.

Based in Brooklyn, New York, Winfree is a singer, songwriter, tattoo artist and actor.

He was in TT for the 2019 Trinidad International Tattoo Fest on September 14 and 15, as well as to visit family. His mother, Hazel White, was originally from Plaisance Park, Pointe-a-Pierre. Sunday Newsday spoke to him about his recent role on the BET’s hit TV show Tales, as well as his other projects.

Winfree, 35, explained that each episode of Tales is based on a hip hop song. His episode, the season two finale, Moonlight, was inspired by the song Moonlight by American rapper and singer XXXTentacion (who was shot and killed on June 18, 2018).

Directed by Winfree’s older brother Bryan Barber, the story is about a young woman who falls in love with a mysterious man.

Winfree plays the character Renfield, whom he described as a crazy, overprotective vampire. Renfield is the “muscle” for the group, likes to set fires, does not trust humans and would do anything to protect his people.

He said the opportunity came about when he was in Atlanta, Georgia taking part in a tattoo convention. Barber called and asked if he wanted to audition for a part.

“He said it was the perfect role for me. He couldn’t just give it to me. I had to really work hard, do my due diligence, studied hard and did a crash course in acting. It was a little intense for me, but it was nice to learn a new trade.”

He said while he was an extra in the independent movie Kill Jane Doe, this was his first big acting role. While acting is not natural to him, he is an artist so it is just another avenue to express himself.

He described the experience of being on the set of a big production as “crazy,” but he enjoyed it and loved working with and watching his brother work.

“I enjoyed getting into character, really studying others to get that character. It was kind of difficult to come out of the character after filming.”

He said he was surprised when he saw himself in the opening scene of the episode, that it was “weird but good, surreal” seeing himself on TV. He would like to do more acting and intends to get an acting coach to further that goal.

However, Winfree’s first love was, and continues to be, music.

“I’ve been making music my whole life. I always knew that I would always do music. My father is a musician, so I grew up listening to him playing music.”

His father, Uriel J Winfree Jr, was a jazz, gospel, and R&B singer who also sang with the group The Spice of Life. While Winfree was growing up, his father played all types of music in their home, including soca and calypso.

As a youth, Winfree was classically trained in violin and sang in the choir at school. He also played football for 20 years in the US Youth Soccer Olympic Development Programme. Now he creates all genres of music but mostly hip hop and R&B. He is also involved in every aspect of his music: production, composition, lyrics, and even the artwork for his albums.

He doesn't make music with any goal in mind – not to have a Billboard album, a hit song, or for fame.

“I sing about life, my experiences, and what’s going on in my environment, my surroundings. Whether people want to listen or not, that’s up to them…I make music for people to enjoy in the hopes they can relate to any of the stories I tell or the situations I feel. I’m not trying to be anywhere per say. We do this because this is who we are. There’s no other option. There’s no Plan B. This is what we do.”

His music can be found on all streaming platforms including SoundCloud, YouTube, Spotify, and iTunes. His song War Cry/ Die Hipster can also be found on the soundtrack for the 2014 movie Dear White People, and another song was in a Geico commercial.

His latest song, Not Today, was released on September 18 and its animated video premiered on YouTube last Tuesday. He said it was about a “classic love story” of a guy meeting a beautiful girl – but she is a devil.


After years in the music business, Winfree decided he needed a change, to re-brand himself, to start over. So 11 years ago he moved to New York from California. There he got a job working at the front desk at a tattoo shop.

Although he had a number of tattoos at the time, he was never interested in creating them. He never even had an interest in drawing before.

“Someone took a chance and taught me how to do things. They gave me the keys to a better life. So I’ve been running with that, utilising the knowledge I’ve got to help other people and to better my life.”

He said every day he is surprised that he is so good at it, and uses his skills to open people’s minds.

“As an artist I feel my job is to challenge other people’s way of thinking and to kind of put them outside their comfort zone. I challenge people to think a little differently."

He's more than a tattoo artist, he says.

"I’m a friend. I have to listen to my clients, really listen to what they want, because it’s going on their body.”

Asked why he felt the need to challenge other people’s ideas, he said because everything in life is not cut and dried.

He said “normal” is different for different people and he wants to encourage people to be happy in their lives, and let others be happy in theirs without judgement.

“I’m not mad that you go to work every day, you put on your suit and tie. I’m not telling you not to do that.

"Why are you telling me I shouldn’t do this? That I shouldn’t tattoo my face, tattoo other people, make other people happy? That’s rude.”

He also enjoys tattooing because his work is always evolving and changing. It ranges from small, simple pieces to large, elaborate work on all kinds of themes. He said in anything there is always more to learn so he did not box himself in to do only certain things.

Winfree works by appointment only out of his private studio in Bushwalk, Brooklyn with his partner Becky Wilson. However, for about ten months out of the year he travels around the world with Wilson tattooing, making music, and networking.

He explained that they travel to attend tattoo conventions, but clients also fly them to different locations to tattoo groups of people.

“Pretty much everywhere we go we have a local there that will basically take care of us, and we become locals. We’re gypsy locals everywhere we go.”

However, he makes sure to return to TT every year, whether it’s for Carnival, Christmas, or the Trinidad International Tattoo Fest.

“This is a home for me. My mom is from Trinidad and my father was raised here as a child. I must come back.”

In the future, he would like to open a tattoo shop in Brooklyn where he and other tattoo artists can work and take walk-in clients. He's also trying to film a documentary about their lifestyle of travelling, meeting new people, highlighting the local scene, and telling their clients’ stories. He's also developing several applications for smart devices, including a tattoo app and a business incubator app.

“It’s a whole package. When you see me you know there’s going to be tattooing, there’s going to be good food around, plenty of good times, happy times, there’s going to be good music, family, friends, people you can depend on. You can always guarantee there’s going to be artistic vibes, and quality. It’s a network. It’s a lifestyle.”

To those who say he has no direction, Winfree said, “Those are the same people who are congratulating me the most right now.

"The people who say I have to choose a direction, choose a lane, that I can’t make music and tattoo at the same time – that’s only because they are projecting their insecurities. Those are the people that limit themselves.

"My ears close up when I hear things like that. I don’t hear it. I don’t see it. If you want to make something, make it, do it, finish it, show it to the world.”

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