In high school, Guy O’Brien started DJing to earn some extra cash. Money was tight, and he knew his mom needed him to help make ends meet where he could. As he got older, he was covering his clothing and personal expenses and was relying on his mother only for food and shelter. This allowed her to spend more money for her bills and his younger siblings, Celeste and Leo.

It was the late 1970s, and rap music was a young, as-yet-little-known art form coming up in New York City. Although Guy lived in New Jersey, a short bus ride from the City, at the time it felt like two different worlds. One night at a party, he watched another DJ, Mark, talking over the music. “I went up to him and said, ‘Why are you talking over the record?’” recalls Guy. “Mark said, ‘Listen man, it’s rap. It’s what they do in New York.’ I thought, I better learn this so I can keep up. Since I was a drummer, I could hear the beat in my head. I heard it as beats, and I heard it as poetry. I thought of it as rhythmic poetry.”

Pretty soon, Guy found he had a natural talent for rapping. He began writing lyrics and performing a little around town. Then one day, fate intervened. He was walking with a friend out of a local pizza place when they noticed a car out front. In the car were a few acquaintances and some friends of Guy’s friends. Also in the car was Sylvia Robinson, the famous R&B singer, who was then at the top of her career. Guy’s friend was quick to bring up his skills. “You gotta listen to this guy,” he said, and got them an invitation into the car. Guy sat down next to another young man who was also auditioning for Sylvia, and the whole group headed off to her mansion up the road.

Also in the car was Sylvia Robinson, the famous R&B singer, who was then at the top of her career. Guy’s friend was quick to bring up his skills. “You gotta listen to this guy,” he said, and got them an invitation into the car.

The other boy’s name was Hank, and quickly, both Hank and Guy started to put on a show for Sylvia and her friends. The two were competing, thinking that Sylvia would only want to work with one of them. Then suddenly, one of the quiet friends in the group stood up and announced that he, too, was a rapper. His name was Mike, and he wanted to audition as well. “He starts doing his thing, and she’s like ‘Oh, wow,’” remembers Guy. “’You know what? Three’s my favorite number,’ she exclaims! ‘I’m not going to choose between the three of you, I’m going to put the three of you together. That’s how we were discovered.’”

Guy (known as “Master Gee,” his stage name), Henry Jackson (Hank) and Michael Wright (Mike) became the Sugarhill Gang, a world-famous rap group best known for the monster hit “Rappers Delight,” which was the first ever commercially successful rap song. It was the first rap single to become a Top 40 hit on the Hot 100, and the three men, only teenagers at the time, quickly became teen heartthrobs on the ride of their lives. “I couldn’t stay onstage after a performance because there were people pulling me off stage,” remembers Guy of their first tour. “You could not hear me talk. It was pandemonium anytime I opened my mouth to talk in public. I was like any teen idol you’ve ever seen in your whole life. I couldn’t leave a venue or walk down the street in public without a security detail around me. I experienced the whole nine yards as a teen heartthrob. Girls would cry or faint in my presence. We did a European tour and travelled all over the world. And we put out several more records that were also hits.”

Fame hit the boys fast and furious, but like so many other young artists without guidance in the industry, they were exploited for their youth, talent, and relative naivete. The three signed to a five-year contract with the record label with terms that left little on the table for them given how much the Sugarhill Gang pulled in for the label. On top of that, Guy wasn’t used to having any significant amount of money; he was 18 and quickly fell into the trap of spending money on cars, girls, clothes, and apartments. He didn’t know anything about investing and didn’t think about saving for the future. One day, at age 23, he woke up and realized that he was completely broke.

It was a major turning point for Guy. All his life he’d loved music, but his years in the industry had taught him a lot of hard lessons. Not only that, he now had a young son. “I never knew my biological father, and I wanted to be a good dad,” nods Guy. “I remember one day I was at the store with my son, and I had $5 in my pocket. I was praying the whole time he wouldn’t ask me for something worth more than $5. It was at that moment that I said, ‘I gotta do something. I can’t have my son growing up in this environment.’ I didn’t have a high school diploma, and I had no job experience. The only thing I’d ever done is tour the world and make women scream!”

From 1985 through 2005, Guy completely left the music business. He turned down another world tour because he had a steady job. His label replaced him with a new “Master Gee.” Many of the fans hardly noticed the difference. The label would have the stand-in rap over Guy’s backing track at shows. Then, in 2005, another fateful event took place. Mike called Guy and asked him to get back into music. Mike, too, had left the record label after being fed up with how they treated him. “Without any question, that phone call was a defining moment in my life,” says Guy. “I made a decision for the first time in over 20 years to do what I wanted. Before that I was doing what people wanted me to do, what they needed me to do, or what I had to do. I had a wife and two other children by then. I had people that worked for me. I was on the Board of Directors for several organizations. But at the end of the day, music’s in my DNA.”

Guy (known as “Master Gee,” his stage name), Henry Jackson (Hank) and Michael Wright (Mike) became the Sugarhill Gang, a world-famous rap group best known for the monster hit “Rappers Delight,” which was the first ever commercially successful rap song.

Guy decided to begin performing with Mike again, but getting the Sugarhill Gang back together wasn’t that easy. The record label still owned the rights to the group, and Guy and Mike fought endless legal battles with the record label over the next ten years. Finally, in 2016, a key figure at the label passed away and his brother was charged to settle the estate. The brother wasn’t interested in continuing the feud with the Sugarhill Gang. Instead, he sat down and worked out an agreement with them. Since 2016, Guy and Mike have been performing as the Sugarhill Gang again, and they’re more appreciative than ever that they have the opportunity to do what they love.

“I fought for many, many years to do what I do on this level today,” reflects Guy. “A lot of tears and a lot of blood have gone into me doing this. I have a responsibility to my legacy, and I also have a responsibility to the millions of Sugarhill Gang fans all over the world. Our fans have been listening to our music since the beginning and have turned their children onto us. I have a responsibility to do it right. Music is my thing. Not very many people get a chance to do their thing at this level. Most don’t. I might walk down the street and pass a man playing the guitar, and in his heart of hearts he’s dreaming of being on the stages where I perform. So I feel like I have a responsibility to that guy. It’s a privilege to do what I do! And I truly appreciate what I’ve been given the opportunity to do.”

Guy grew up around music. Born in Manhattan, his earliest memories are of his maternal grandparents who owned an audio equipment store called Crazy Eddie’s in Brooklyn. “My grandfather, Peter, would always have new microphones and speakers,” recalls Guy. “He was the first person to show me how to be successful and how to carry yourself. I didn’t know what wealth was back then, but I thought everybody had a store. I thought everybody would fly to Jamaica every couple of weeks!” Guy and his mother lived in a nice apartment next door to his grandparents, in a swanky building with a doorman for several years. However, the relative peace of those early years didn’t last.

Guy’s mother had had him when she was 16, which was much more taboo at the time. As a result, she had a strained relationship with her mother. She eventually met a man and moved away from her parents with Guy. She had a second child, Guy’s younger sister Celeste, and endured poverty, violence, and abuse at the hands of her boyfriend. By the time Guy was seven, the two had split up, and his mother was dating the man she went on to marry. The man who would become Guy’s stepfather. The family moved to Englewood, New Jersey, where Guy’s younger brother was born and where they settled.

Guy had a complicated and troubled relationship with his stepfather. “Dad was a pilot, he taught flying, he was an accordion player and trumpet player, he could take apart a sports car and put it back together. He was phenomenal, he was a quintessential renaissance man,” says Guy. “He was an amazing person and was one of the most intelligent people I’ve ever met in my life. But he had a terrible mean streak.” Guy’s stepfather was physically violent and abusive to his wife and the children.

“I was afraid all the time,” remembers Guy. “I was deathly afraid in my house. The only relief I’d ever get would be when I’d leave the house. Anytime I was home, a situation could go from bad to worse at a moment’s notice. The way I am with my children is a direct result of how he was. I never wanted my children to have that feeling of living in fear of me.”

Still, Guy looked up to his stepfather in a lot of ways. He would bring Guy to the airport and take him flying in the plane he co-owned with a friend. He taught Guy how to work on cars. And most of all, he introduced Guy to making music. Music and musicians were everywhere in their home, and Guy would spend hours with his stepdad in the studio where he was a recording engineer. “In every studio, there’s a piano and a drum set,” explains Guy. “I liked to bang on things, so I was drawn to the drums. Whenever he would go in there, he’d find me on the drums. One day he says, ‘You like the drums? I’m gonna teach you how to play.’ So he signed me up for lessons, he encouraged me, he got me a drum set later that Christmas. He’d make me practice and would encourage me, but I still lived in fear knowing that he might punch me in the face if I didn’t do one of the assigned chores right. It was a weird situation in which I loved him and hated him at the same time. He had a positive influence on me, as well as a negative influence.”

“Anything that anyone would admire in me, I got from my mother,” asserts Guy. “I admired her ability to be able to handle whatever was in front of her.”

By the time Guy turned 15, his mom and stepfather split up and left the family struggling to make ends meet. Regardless, throughout all of the hard times, Guy always remained close with his mother. “Anything that anyone would admire in me, I got from my mother,” asserts Guy. “I admired her ability to be able to handle whatever was in front of her. She was a true soldier. She dropped out of school to have me. She taught herself bookkeeping and got a job as a bookkeeper. I have no idea how she was able to do it, but she ended up being in book publishing. She always figured things out. She put food on the table for three kids as a single mom. She was abused physically, but she figured it out. She always landed on her feet, no matter what happened. I admired how bold she was. And in a room full of people, she always stood out. She had a huge influence on me.”

It was after their divorce that Guy decided to start earning some extra cash from DJing, and the rest, as they say, is history. He left high school to go on tour with the Sugarhill Gang. After a whirlwind few years at the top of the industry, Guy found himself broke and looking for a job, any job. Like most people did at the time, he started by checking the classified ads in the newspaper, and one ad caught his eye. It was a job with a magazine subscription company. The ad read, “Free to travel. No experience necessary. Representing lead publications.”

Guy called the number and was asked to come in for an interview. The manager told him he’d be sent on the road for weeks at a time and would have food and housing covered. Being embarrassed about his financial state, it was exactly what Guy had hoped for. He wanted to get away from New Jersey for a while. He accepted the job and ran back home to get a few things and borrow $10 to get back to New York. With nothing but an old overnight duffle and a garbage bag, Guy hopped in the back of his new boss’ Buick, and rode up to Springfield, Massachusetts to start his new career.

Almost immediately, Guy was recognized by one of his roommates; it was a situation he’d hoped to avoid. And within a day, word got out to the rest of the staff; his roommate immediately began spreading the word that they were working with Master Gee. But Guy kept his head down and focused on learning the business. His job was to sell subscriptions door to door, but his job training didn’t exactly inspire confidence. He was matched with another salesman, who immediately left to smoke a joint in a nearby park. Then he would get a drink at a local bar before he finally visited a home, sold a magazine, and stole some of the money from his sale.

“Someone eventually came back to pick us up, and the trainer tells me, ‘Hey man, you’ll be all right. You’re ready to go out on your own.’ And I’m saying to myself ‘What do you mean I’m ready?! I saw a guy smoke weed, drink a beer, and steal $5!’ Fortunately, I always had the ability to adapt,” laughs Guy. “I grabbed a credential and at first I kind of struggled through it.” He managed to make a couple of sales on his first day, which he learned later was unusual for a new recruit. The next day, his boss noted his success in the field, and Guy quickly rose in the ranks. Before long, he was promoted to field supervisor. He began making real money, and the business owner wanted to invest in Guy. “He told me, ‘Show me you can save $10,000, and I’ll give you five of my people to start your own business,’” recalls Guy. “He was my first real mentor. Eventually, I got to that point, and I built that business from five people to over 50 people. I went from getting a $7 advance when I first walked through the door to making millions doing it.”

Eventually, Guy’s old boss made the decision to retire and sold his customer service business to Guy as well. By this time, Guy was on the Board of Directors for the National Field Selling Association, had a house in Chicago and Los Angeles and was, by his own account, “quite the corporate guy.” He had created a new life but something wasn’t right. “I was highly successful. I had all the trappings of success, but I was miserable,” Guy admits. It was then that Mike called him and asked him to take the leap back into music.

Guy doesn’t regret the years he spent building his business career. On the contrary, he did what he did for his children and is happy to have been able to give them the stable life he never had. In fact, he considers one of his prize possessions to be a painting his daughter made for him for Father’s Day when she was in Montessori school in 2007. “It says, ‘To the best dad,” Guy smiles. “I used to carry it with me but now I have it on my nightstand. I always wanted to give my children the greatest life that I could possibly give them. I left music, I left what I love, to take care of what I love.”

To young people starting their careers today, Guy advises care when building your team. “Create your team before you do anything,” he warns. “Talent with no team is no talent. Get somebody that can help you manage your team and get somebody else who will give you legal advice. Always know what you’re good at, and be honest about the things you’re not good at.”

These were lessons Guy had to learn the hard way, but thankfully, through decades of work and struggle, he ended up right back where he needed to be, with the Sugarhill Gang. “I’m fortunate, I’m successful, I’ve got cool stuff, but that’s not what’s important. The trappings of success are just a byproduct. The performance is the greatest thing. It’s amazing! When I cross the threshold of that stage, I’m Master Gee,” smiles Guy. “There’s always a point in the performance where I transition to Master Gee and am no longer Guy. I’m not thinking about what I have to do. I’m just Master Gee, and I’m rocking the crowd.”