When Macy Gray released I Try, the biggest hit of her three decade-long career, she was 31, a single mother of three children and resigned to another career after a record deal ended four years earlier.

Growing up in Canton, Ohio, she was mocked for having a squeaky, high-pitched voice and stayed quiet as a child, barely able to hold a conversation until the of age 10. But singing brought a Grammy Award, 10 studio albums, and an acting career including Spider-Man and Training Day. In 2012 a music critic at The New Yorker described her vocals as “like honey with the stingers left in”.

“I understand myself more now,” Macy says. “I understand what being a mum is. I understand what my purpose as an artist is. And I trust my gut.”

Worst habit?

Video games. Right now it’s Grand Theft Auto and a basketball one. I’ve been playing video games since I was a kid. I love it because it’s a great way to waste time. It’s nothing about you. You’re not thinking about anything, and it doesn’t matter if you win. The detail of the games is beautiful to look at. In the basketball one, you can see them sweating. It is a colossal waste of time. I’ll think, “Oh, I could have been doing this. I could have done that.” But, it’s fun. What are you gonna do?

Greatest fear?

I’ve always been afraid of heights. The other day I was in Los Angeles and there’s lots of hills and I made a wrong turn. I went up this massive hill, and it took me forever to turn around because I was so scared. I just freeze. My whole body stops. I don’t have it with looking out of planes. There’s just clouds. Nothing’s gonna happen. It’s being in open spaces where I literally freeze up.

The line that has stayed with you?

Before my father died [stepfather Richard McIntyre, who raised her with her mother, Laura McIntyre], he asked me if he had been a good dad. It’s a moment I’ll never forget. He was very alpha. I never ever saw my dad be anything less than all-on, on-10, Energizer Bunny. He had cancer, so we knew he was passing and, when we were alone, he asked me that. He was crying when he said it. He didn’t say, “Make sure you take care of my car”. He wanted to know if he had done well as a person. I said, “Yeah”. I was kind of choked. My dad taught me everything but that was the biggest lesson he ever taught me. He died in 2009 and always keep that in mind now when I’m making decisions.

Biggest regret?

Honestly, that I didn’t spend more time with my kids [Gray has three adult children with her former husband, Tracy Hinds] when they were younger. Their dad wasn’t around, and I didn’t realise until years ago that if I was gone and the dad was gone, they wouldn’t really have somebody. My mum and his mum were around, but that was sporadic. I was in my 30s, and I was still partying. You can’t really go back and fix things. You can only go from here. I have a grandchild now. He just turned two. My little baby boy. Having grandkids is the best thing ever, and I didn’t understand that until I had one.

Tell us about your turning point...

I was playing at a club called The Roxy in LA in 1994. An A&R guy saw me. I got signed, made a record, but I got pregnant again and they dropped me. I wandered around aimlessly for a few years. I went back to live with my mum because me and my husband split up. Then a guy from Universal Publishing got my mother’s number and called me. I was eight months pregnant at the time with my third. I went back to LA, and the turning point was when my first record [On How Life Is] came out in 1999. Things changed drastically. I got really popular. I had money for the first time in my life. I had people around me I wasn’t expecting. I was going to parties with people I was used to seeing on TV. I’d be sitting there and there’s Elton John talking to me, going “Hey, Macy”. I didn’t know what to say. I was just very, very fortunate.

The artwork or song you wish was yours?

Redemption Song by Bob Marley & The Wailers. I have sung it, but I didn’t have the same understanding of what he was talking about then as I do now. I feel like I would sing it completely differently.

** If you could time travel, where would you choose to go?**

The future. I can pick a lottery and get the numbers. I could invent something before the person invented it. I could do a whole business out of telling people’s fortunes. But I believe our spirit and our gut knows what’s going to happen. I think we miss those signals sometimes.

**Macy Gray plays The Arts Centre Melbourne, September 11; Hindley Street Music hall, Adelaide, September 12; Anita’s Theatre, Thirroul, September 16; Wrest Point Entertainment centre, Hobart, September 18; Sydney Coliseum Theatre, Sydney, September 24 and Enmore Theatre Sydney, September 25. **