With nothing to lose and everything to prove, he walks up to the mic, a crowd of people behind him preparing to judge his every word. The beat drops, the camera focuses on his face, and he releases a torrent of phrases that have been building up inside his head.
Just like any skill that one hopes to excel at, rapping is no exception. If you want to be the best, practice makes perfect. Jay Tyson of Newport News, aka TAILORMADE TYSON, has been working on the art of his delivery since he was able to talk. Now he’s being tested by his peers, having his freestyles recorded and being posted on social media outlets like Jack Thriller’s rap-battle series “16orBetter” for others to openly judge. But judgment is nothing new for the 24-year-old artist. Whether it’s been in his personal life or in his work, Tyson has forever been a student at the school of hard knocks.

“My mom used to tell me stories about how I would rap the words to songs my dad used to play at parties, and I’d entertain guests,” Tyson said. He must have been three or four at the time. “I guess you could say that even then I had a knack for performing and making music.”

He wrote his first song for fun at seven-years-old and slowly started taking music more seriously as he approached middle school. He was the kid that sat at the lunch table with his notepad, scribbling down lyrics as he freestyled aloud. Other students used to come up to him and ask why he was talking to himself and he’d have to explain that he was rapping. He didn’t feel like he had to go into greater detail because his close friends knew what he was about. It was a form of therapy that helped him deal with stresses at home or in the classroom. But eventually people would ask him to rap so they could hear what was coming up with, and Jay would spit a few lines off the top of his head. As he started to get positive feedback from people he didn’t know, he realized that maybe he had a talent that he should focus on.

The focus did shift as he coasted through the rest of his middle school years, continuing to write lyrics and develop his style when teachers weren’t paying attention. Some of the other kids were noticing though, and Jay got invited to participate in freestyle battles, known as “cyphers”, during lunch or between classes.

“These cyphers were important, you had to come with it ‘cuz if you were whack or got booed, you might get banned from future cyphers,” Tyson remembers. “I was always prepared though, with something I’d been working on the previous day or minutes before in the class that just got out.” The battles helped Jay with his confidence as he impressed other aspiring rappers and made connections with people that wanted to make music. The music was becoming an extension of himself, and through it, he found an emotional support system.

In high school he started making his name as a local artist. His headphones ever-present, he was taking cues from legends like EMINEM and NAS, studying the art of storytelling. He had become close friends with some of those other rappers from cyphers and even guys who were involved in producing and had their own recording equipment. The most important thing this cast of characters had in common though was their drive to make something real. They weren’t just looking for fame and fortune; they wanted to make an impact on the state of hip-hop music.

With their help, Jay put out his first mixtape under the name MEDIEVAL in 2007 when he was 17. After a few more mixtapes with the MEDIEVAL moniker, he officially changed his name to TAILORMADE TYSON, a title he feels has more potential for brand recognition. His most recent release is 2013’s The Stoner’s Guide to Getting High—a collaboration with his cohorts in a team called the Cut the Check Clique.

“Stoner’s Guide” may have a slightly off-putting title to casual hip-hop fans, but the depth of the songwriting and production extends beyond the world of cannabis consumption. It’s Jay’s most polished and mature effort to date and showcases his ever-improving grasp of lyrical delivery of emotional content. Of course, as the title suggests, there is plenty of discussion of marijuana, but it’s presented as a lifestyle choice that has helped many people get through hard times.

Jay has a mic, boombox, headphones, and music note tattooed on his right arm, showcasing his passion and just how seriously he takes his art. Sometimes he gets so invested in his dreams of hip-hop success though, that the grind of the everyday norm can drag him down. He has a job that helps support his young family—a woman he loves dearly and their young daughter—but to know Jay is to see that he won’t be satisfied with himself until he breaks free of the nine-to-five lifestyle and the frustrations associated with living paycheck to paycheck.

“I want to make music, not just be a rapper. I want to make timeless and authentic music that people can relate to,” Jay said. “I feel like there’s a lack of authenticity in today’s hip-hop. I want to show people it’s not all cars, drugs, hoes, etc. and give them a piece of myself.” He recalls a conversation with an older gentleman who downplayed today’s music and criticized its lack of character and relatability. “I wanted to defend my genre, my art to this man, but I could barely count on both hands the number of timeless records released in the modern era.” The conversation was an important turning point in his writing style and has helped shape his recent songs that discuss more relatable subjects like family responsibilities and dealing with self-doubt.

As Jay continues to hone his craft, you can bet his headphones will always be near, and you’ll be able to hear his train of thought as he spouts new lines. His hands will be moving to punctuate each rhyme and provide a visual illustration of his artistry. He has no doubt that his perseverance will pay off, and in many ways, success is starting to come his way. In May 2014, TAILORMADE TYSON had a song receive radio play on the Hampton Roads station, 103 Jamz and more radio play may be in the immediate future. His appearance on the “16orBetter” rap battle has received critical acclaim from fans and Internet users who had not heard him before. With the wind at his back and a number of new tracks in the works, it looks like Jay’s career may be starting to reach that natural high.

For more updates on TAILORMADE TYSON, be sure to “like” his Facebook page, follow him on Twitter and Instagram, check out his rhymes on Soundcloud, and download his mixtape The Stoner’s Guide To Getting High on DatPiff.com.

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