BlackBook Interview: Macy Gray on Her New Music + Her Incredible Legacy

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Photo: Giuliano Bekor


It’s been nearly twenty years since Macy Gray released her first album, On How Life Is, which spawned the Grammy-winning mega hit “I Try.”

Eight albums later, she’s back with a new studio record, Ruby, and its buzzy, bright lead single “Sugar Daddy” is one of our sincere contenders for song of the summer. The track was co-written by fellow Grammy winner Meghan Trainor and is accompanied by a smoky, glittering music video featuring Diana Ross’ son and Gray as a down-on-her-luck lounge singer.

The new album, Gray describes, is as personal as it is varied: she describes groovy up-tempo songs, soulful ballads, and tracks she can only explain as something she’s been listening to on repeat. It’s out September 7th.

We caught up with singing legend, reflecting upon Gray’s proudest career moments, the legacy of “I Try,” her experiences with the #TimesUp movement conversation, and the artists she’s currently drawing inspiration from.



I wanted to start by asking you about this new album, and the songwriting process behind it.

It was written in pieces over about a year and a half. It started out with – I did a song on Ariana Grande’s album, Dangerous Woman, and I went to the studio of the producer of that album, Tommy Brown; he said, ‘We should do something together.’ I came back the next day, and we’ve been working together, for about a year and a half. I posted up with a whole crew of songwriters and producers over that time and worked on it with them as well.

Were you drawing on personal experience or stuff going on in the world as you were writing? What was inspiring you?

It’s a very personal album. There were other writers involved, so it was a combination, but they mostly wrote…it geared towards me and what I wanted to talk about. It was all really whatever I was going through at the time that ended up in the songs somewhere.

You mentioned the Ariana Grande collaboration – did she reach out to you?

I had never met Ariana before that, and I went to take a meeting with her label, Republic Records. An old friend of mine is head of A&R there. She said, ‘Why don’t you get on this Ariana Grande record?’ She sent me over to Tommy’s, and we hit it off. I didn’t even meet Ariana until after, at a birthday party she had that I went to way after the fact.

With ‘Sugar Daddy,’ did you come up with the concept for the video?

The song can mean so many things, so one of my favorite movies is Lady Sings The Blues. And there’s a favorite scene in there where she’s singing for money. So essentially that’s what we did with the video. To show everyone where I’m at… and it’s a love story. It’s kind of like my whole career in a simple visual. We got Diana Ross’ son Evan Ross starring in it. She saw it and she loved it, so I’m really happy.

How was it working with Meghan Trainor?

She’s adorable. She was actually working on her album with Tommy, and she came by the studio and ended up writing on my album, because she’s such a big fan. She came back the next day and the next day. She wrote the idea for ‘Sugar Daddy’ when she was 16 – it was one of the first songs she ever wrote. She had it hiding in her head somewhere. She went ‘I got this idea.’ And we finished it off.



Can you walk me through some of your favorite tracks? What were the most difficult to work on and the most fun?

There’s a song about living in the moment, living for right now. We have a feature by Gary Clark on there. I love the whole album, of course, but the very last song – I listen to it all day on repeat. Then there is a ballad I really like. But I really love all the songs, we spent a lot of time on them. Every song is super crafted.

And the title Ruby – what’s the significance of that?

Red represents emotion, and all the songs are about emotion, and feeling from the heart – and the heart is red. It’s a jewel, and it’s a jewel for me to be making an album like this, 20 years later. Jewels, and red: a bright awesome color that you also see when you’re nervous about things; and I’m nervous about the album coming out, so it’s just representative of everything I’m doing at this point in my career.

It’s been almost 20 years since On How Life Is, your first album. Do you feel like you and your approach to music have changed a lot, since you started?

It’s an entirely different process now because of technology and what’s available to artists – and the kind of music that’s out, and who runs the music business now. So I don’t think it’s really possible to do what you did 20 years ago today. But as a person and an artist, I’m a much better singer than I used to be. My life has changed, so I have different things to sing about. I’ve come a long way since my first album, musically.

Do you think this recent conversation with #TimesUp and #MeToo has had a big impact in your sphere of music?

I come from a different mother, you know? I’m from Ohio, and my mother was a ‘Take no shit’ kind of mom. Not to have any criticism of women who go through that, but I have always been able to avoid it, or nip it in the bud before it got started. But I do know that it’s rampant all over the place, especially in Hollywood where girls want to get their career going, constantly thinking you’ve got to do whatever it takes and getting caught in really dark situations. I’ve been fortunate to be able to handle things before they happen.

You’ve allowed some time to breathe between albums. Do you spend most of your downtime thinking about the next album – do you feel like you’re always working?

My mind is always going, I’m a musician, so…you can’t help but be creative. As a writer, you hear people say stuff and think about how you’re going to write it down. I’m the same way. I think in art. But I’m not working all the time…I’m actually a bit lazy.

Obviously, ‘I Try’ was such such a big song. Did you think it would be so successful if you made it now?

No, I actually was begging my label to put out another song. I didn’t think that song was a hit – that the chorus was too wordy. I was arguing with my label about another song, but they didn’t listen to me, which was a good thing. And, like, six months after my record came out that song hit. I was touring, and I was doing a lot of promo, magazines and stuff, but it was all new to me, so I was having a ball and not really counting my record sales. But the record came out in August ’99, and I don’t think ‘I Try’ hit until the next year. I was in Europe, and my manager called and said ‘Your song is number one.’ I didn’t even know what that meant. I was totally blown away. And the fact that I still sing it, and everybody knows every word, and I go to the mall and they’re playing it at Urban Outfitters, and in movies, and commercials, and stuff. I’m way more shocked than anyone. I had no idea.



What was the song you wanted them to release instead?

They did release it after I begged them, but I don’t even think they wanted to. It was a song called ‘Call Me.’ I thought that would be a massive hit. They were right – that song didn’t go. So I learned early that I really don’t know what I’m doing, and I should just stick to singing.

What about other moments in your career that have been your most proud? Even if they weren’t commercially your biggest?

This album, I’m super stoked about. I’ve been able to travel all over the world, to places I didn’t even know existed. I did this festival in the UK called Glastonbury. And I headlined there and that was a huge deal. I was selling out arenas. The fact that I still do big theaters and people still call me when I have an album out, it feels so good. I remember taking my mom to meet President Clinton, she was really happy about that. She met President Bush, because I did something for him. It’s cool to take your mom and your dad around. I got my mom backstage tickets to Tina Turner. She met Tina Turner, and she’s a huge fan. Little stuff like that, you’re glad you can pull off.

Are there other artists inspiring you right now, or that you’re listening to currently?

There’s so much music now, there’re tons. In terms of who I’m listening to now, I don’t even know who I’m listening to. I still really love Pusha T’s new album. I listened to that a couple days ago. Kendrick is always really inspiring. There’s so many, there’s a lot of great songs coming out – I don’t know that there’s one particular artist I’m following. I think Anderson Paak is cool. I think what Childish Gambino is doing is really groundbreaking. Not everyone is forced to be so commercial anymore – people are doing what they want to do, and it’s working.

Are you going to do any more acting work in the near future?

Yeah. I got so busy with my record, I had to turn down some stuff. I think next year is going to be crazy too, but I do want to do more movies. I haven’t been able to fit it into the schedule, and drop three months and go focus on film at the moment. But I do want to do that, definitely.

Do you have anyone that you really want to collaborate with in the future that you haven’t gotten to yet?

Gosh, I don’t know, it’s kind of an arrival if you get Jay-Z on your album. That’s something huge. Then you’ve definitely made it. I don’t know how soon that’s going to happen, but he’s someone I’ve always wanted to do. I’m still a big Kanye fan, I think he’s a great, great record maker. That would be cool. There’s a lot of people that I’m into.