Nearly 14 years ago, singer Macy Gray made her biggest splash with her debut album, On How Life Is, and its hit single, “I Try.” Back in July 1999, Gray intrigued audiences with her unique sound and retro look for the first time. On How Life Is went on to sell more than seven million copies worldwide; “I Try” won for Best Female Pop Vocal Performance at the 2001 Grammy Awards.

Gray has put out six albums since then—including last year’s Talking Book, a complete cover album of the Stevie Wonder classic—and is currently working on another. She’s also acted in acclaimed feature films, including For Colored Girls, Training Day, Idlewild and, most recently, last year’s The Paperboy alongside Matthew McConaughey and Nicole Kidman). Currently, the 45-year-old singer is on tour celebrating the 14th anniversary of that very first album.

“I’m very excited to get back on the road and revisit music and a time in my life that was so influential in making me the artist and person I am today,” Gray says. caught up with Macy to discuss the album, subsequent changes in the music industry, and her life.

EBONY: Tell me about the current tour. How did the idea come about to celebrate On How Life Is this way?

Macy Gray: There was a lot of demand. I always get a lot of tweets and comments on Facebook about the album. It was just an idea that we had and we ran with it. The tour is really short. We’re only doing six shows along the East Coast. We’re really doing it for fun and to see how it goes. Maybe we’ll do it again next year all over the world.

EBONY: On How Life Is came out in the summer of 1999. Who were you then, and what was life like?

MG: There was a lot of set up for the album at that time. I got signed about a year before. We made the album in about six months and there was a lot of work to do even as we were making the record. I didn’t know anything about the record business or how things were done. I was just so excited to have a record [and] be on a record label finally. I wasn’t really expecting anything. I was just in the moment.

It was very different, because now you have to pay attention to what’s happening on the radio and all that other stuff. But when you’re new, you don’t know anything about that. I think that’s why a lot of people’s debut albums are so pure, because they’re not tainted with all that business yet. When it did blow up, I was totally surprised.

EBONY: In an article for The Guardian, you said the only song from the record that you still listen to often is “I've Committed Murder,” that it was the culmination of all your hopes for the album.

MG: That’s still one of the best songs I’ve heard. That song is so great. It’s the production on it and all the details on the record, even what it’s about. I just love that song. It’s really a great record. If it were anybody’s record I would say that. [But] I wouldn’t want to go back there musically. So much has happened since, and I have so many other influences. But it’s still special to me.

EBONY: So the album comes out and was a huge hit. In retrospect, what do wish you could tell yourself about the experience ahead?

MG: I would say, “be smart.” I was having so much fun, and a lot of times I wasn’t paying attention to the big picture or thinking about the consequences of what I was doing. I was really impulsive in terms of things good and bad. I had a really good time, and I’ll never regret that, but I wish I had been more conscious.

EBONY: “I Try” was, of course, the smash single from the album. Do you ever get tired of singing it?

MG: I’m a fan of that song myself. I love that song. I can’t think of a time I’ve ever been tired of it. I wish a lot more people knew my other stuff. Overseas I have a long list of really popular songs. It would be cool if my later records would have been promoted better here in the States. But I’m making a record that’s really awesome and I have a new manager. Everything is fresh and I’m excited about my new record.

EBONY: So tell us about the new record. What’s the first single like?

MG: It’s wild. It’s raw, like nothing you ever heard before. It’s ghetto, Black, White, red, yellow, green. It’s all kind of things. Most of all, it’s new. You haven’t heard it yet.

EBONY: You’ve released seven studio albums. That’s a lot of work. How have you seen the music industry change?

MG: Is it that many? The music industry is a whole different world. There are fewer labels, less everything, and there’s not as much variety. When I was in high school, jazz was really popular, and reggae was still really popular, and hip-hop was blowing up all over the world. Everything is kinda homogenized now. There was so much juice, and you could be a fan of so many things. Now there’s a lot of homogenized music. It’s like, I heard Pitbull on a Tim McGraw record the other day, which is cool. There’s just not a variety anymore, and it’s a lot more producer driven than artist driven. It’s not bad, just different.

Donovan X. Ramsey is a multimedia journalist who writes about all things social, political, cultural, financial and whimsical. Follow him on Facebook and Twitter @iDXR, or