By Marc Choquette | August 7, 2009

When the Entertainer interviewed R&B star Usher back in 1998, he was only twenty years old, and touring to promote his new album My Way. The now multi-platinum album went on to sell eight million copies worldwide, and Usher quickly rose to the top of R&B artists in the late 90s.

Eleven years later, Usher is still a force in the industry, and has sold 38 million albums to date. Billboard recognized him as one of the most successful Hot 100 Singles artists of all-time, ranking higher than any other artist of his generation.

He has always had an interest in philanthropic activities as well, founding a non-profit charity called New Look, which encourages young people to take a “new look” on life through education and real-world experience. Following Hurricane Katrina, he was among the artists who signed up for the Katrina relief concert, and also founded Our Block to help with the re-construction effort in some of the devastated sections of New Orleans. He has also done a Public Service Announcement entitled “Do Something,” which encourages youth to engage themselves in the local civic environment.

Usher founded music label US Records, a subsidiary of Clive Davis’ J Records and Sony BMG. He as introduced, via his label, such acts as rapper Pico Love, singer Rayan and R&B vocal group One Chance. He is also a part owner of the Cleveland Cavaliers, and is now worth an estimated $375 million.

In this 1998 interview, Usher speaks about growing up and his mother’s role in his career, the process of recording My Way, and how he’s dealt with fame and fortune.

Read the complete interview after the jump:

R&B heartthrob Usher — Doing it his way

August 20, 1998

Usher, the nineteen-year-old recording star who calls the music he makes “hip hop soul pop” is making his transition into manhood his way. Usher Raymond’s “way” was just what executive producers L.A. Reid, Babyface Edmunds, and Jermaine Dupris wanted to capture when constructing the songs that would make up his multi-platinum CD, “My Way.”

“What we ended up writing and recording is about my life, about what I’ve dealt with, being a teenager, going into manhood. It’s about my feelings, “said Usher. The first single from the album “You make Me Wanna” reached #2 on Billboard’s Hot 100 chart, second only to Elton John’s Princess Diana Tribute, “Candle in The Wind.” A series of performing and acting engagements followed, including appearances on Live with Regis and Kathy Lee and the Tonight Show. His acting debut on UPN’s Moesha, starring opposite Brandy (Atlantic Records), led to a recurring role on the soap series the “Bold and Beautiful.” In October, he will start a new film called “Light Up.”

Raised by his mother, who also manages him, Usher and his younger brother moved to Atlanta from Tennessee when Usher was twelve. Usher started signing in church choir and was spotted by a LaFace records’ representative at a local talent show. While his counterparts covered gangster-rap, Usher left out the profanity and sang from the heart. After an initial slow start, during the time that his voice changed, his recording career skyrocketed.

From the Beverly Garland Hotel, Usher and his mom, Jonetta, spoke to us in a personal interview. Asked how she balances the job of being both mom and manager, Jonetta answered, “I feel that every parent needs to pay close attention to what their child really wants in life and help them, even if it means denying yourself.“

“I try to teach him to always be himself. I tell him, ‘Set goals for yourself, and go in and get the most out of everything you do. And don’t depend on anyone.’ I try to give him my experiences and advise him-then I leave it up to him. I really raised him to know the difference between right and wrong. I let him know how I feel about things, and then he makes the decisions. He’ll ask me about a certain girl, and I will tell him how I feel about it. It doesn’t matter if it’s good or bad.”

Asked when Usher showed signs of talent, Jonetta stated, “I noticed it at the age of nine. He started out in my youth choir. When I saw him perform around the age of eleven, I knew he had true potential to be a star. He had something special. I think this is why his career has taken off the way it has. He’s just being himself and not doing it to please other people. It’s truly him and he loves it.”

Usher is on tour opening for Janet Jackson and scheduled to make a San Diego Appearance at the San Diego Sports Arena on August 28, 1998.

Usher, is it scary opening up for a large act like Janet Jackson?

I’m never scared, I may have butterflies but I’m never scared of an audience. That’s what being an entertainer is all about.

What does Janet Jackson think of your choreography?

She says she loves it.

Why do you think your music appeals to more than one generation and to more than one market?

Just because I’m young. Older people have already gone through what I’m going through, and young people like the fact that it’s cool, it’s hip, it’s young and energetic. But my personality comes across on the tracks. If you don’t really believe in what you are singing, people are not going to receive it. It’s just another song. That’s why it took time for Jermaine Dupri to find out what I would sing about, what I would talk about. And when I perform the song, I can add more emotion because I have gone thought it. It’s about my experiences.

How much of you is in the CD?

All of me. On every last one of those songs. I have experienced what I sing about at one time, or, at least, have come close to it.

What is your favorite song to perform live?

I always love doing Bobby Brown medley. It takes people back, and it expresses a variety of things. There is a lot of dance “old –school” in it. I perform “Rock with You” “Tenderoni,” and “Every Little Step.”

It’s unusual to hear a song that expresses a conversation like one you hear in “My Way.” Who thought of those lyrics?

My contribution came from making the song believable. My producer, Jermaine Dupri, actually followed me around and wrote stories about how I roll. And then, just having a hip-hop twist on it, it all came together.

I heard that Jermaine Dupris asked to listen in on your phone conversations.

He was seeing that I had “game,” you know what I mean? That I have a good rap on the telephone. A lot of the things that were written were things that I was really going through. Every time I got on the phone, he would listen to how I talk and how confident I was in conversation — what I had to say, what I would talk about, and my reason for calling the person. He might turn the music down and say to me ‘yo,’ and I would tell the person to hold on for a second, and then he would listen in on my conversations.

At one point in your career you struggled with your voice changing and your first record, produced by Puff Daddy, didn’t sell as well as you had hoped. Producer Jermaine Dupri took a different approach with his method of artist development. What did those struggles teach you about the music industry, and why is “my Way” more successful?

You have got to be true to who you are. You can’t go out as a “fad” in the industry; you have to be true to who you are, and I figure that’s the reason why, maybe, I didn’t have as much success with the first album. That wasn’t me. That’s something Puffy wanted me to do, and it was a fad. Fads fade in and fade out whereas with “My Way,” Jermaine Dupris spent time to get to know me as a person. He just took what I had and wrote about it. He didn’t try to change me or make me do a certain thing. He made suggestions as far as dressing, but that is just something you do with your homeboys. You might, collaborate with each other. Like say, ‘Hell, what do you think about these tennis shoes, you know? How would you flip this outfit?’

Then eventually, I developed my own style. For example, I always wore a skullcap. That’s just something that was made bigger, but I really hooked it up and put it together.

If you could have two magic genie wishes with one being spiritual, one being professional, and one being personal, what would they be?

My spiritual wish would be to finally see God’s face … but I guess I would have to die for that. You have to stay close to God for that, and that’s my wish. My professional wish is to have longevity, to have popularity and prosperity far beyond any other artist. But it takes time to get that. My personal wish would be to have 100 more wishes.

Do you keep track of your record sales, or do you leave all the business to mom and just stay in the creative mode?

I live by the microphone, and my mother takes the business side, but she shows it to me. Definitely. I’m aware of what is going on with my money and my finances. My mom is my business manager though, and I do the artist side.

Is your album double-platinum?

Four times platinum.

Since you’ve gotten so successful, have you purchased any special gifts for your family?

I purchased a Mercedes Benz for my mom. My brother James is thirteen. I bought him a Kawasaki motor bike, cloths, tennis shoes, video games, and CDs.

What issues do you and your mom buck heads about?

Issues. Hmmm. The fact that I don’t always do what I say I’m going to do and … women. Every man has time in his life when he’s kind of blind to what the girl he’s talking to is all about, my mother has her opinion. My mother has a point. But maybe it doesn’t always apply.

I mean, how can you say what a relationship consist of if you aren’t a part of that relationship? I would say to her, ‘Why don’t you try to be friends with my friends? I’m single, you know?’ I don’t really have time for a relationship. That was what she was fearing, and I tell her, ‘Don’t worry about that. I’m single. I can have friends.’

In many ways you have been a positive role model for America’s youth. You are the national spokesperson for the U.S. Department of transportation’s “Get Big on Safety” campaign and participate in the NBA Stay in School Program.

It felt good to give back to the kids. I feel like they are our tomorrow, and we have to pay attention to them. We have to be quiet enough to hear what their needs are and try and help them out. I’m setting up a lot of things in my business nowadays. I’m doing a foundation. I try to stress how easy it is to do something if you just put your mind to it.

Do you feel a responsibility to our youth because of the public attention you get?

There is a responsibility, but at the same time you try to live your life. You try to do everything and make the same mistakes that every other kid will make at the age of nineteen, and then you realize you can’t make those mistakes because people will take it the wrong way. You have to give up a lot of your privacy.

When you date, do women find it difficult to get past your player image?

Well, I wouldn’t say I’m a player. The sex appeal is just me. I’m confident of myself and my sexuality, and I guess that’s the reason why I can’t the way I do on stage, but it doesn’t mean I go out in the street and hung on everybody. It’s just a performance. “My Way” was about a girl that was a friend of mine, but her boyfriend couldn’t accept the fact that we were friends. That is the reality of it. Her boyfriend was so jealous that I would play it off like we were doing something. I never said we were sexually active, but I would say ‘You can get mad if you want to, but one day she’s still going to give it up.’ I guess that’s where that comes from. The song “One Day You’ll Be Mine” was just a song … I met a girl, and I really dug her. I liked the way she looked, and we started talking. I said, ‘One day you’ll stop this and be mine.’ All of those aren’t player moves … it’s just reality. Those are all romantic things I felt, but people will interpret it the way they want to.

What kind of music do you listen to?

I like a variety. I like to see an artist show variety, that he or she has versatility. I like to hear hard-core-rap — don’t get me wrong — but I also like to listen to Maxwell at the end of the day.

What’s the best advice your mom ever gave you?

Strivers achieve what dreamers believe.

How often does she say that to you?

She only had to say it once for me to remember it for life.