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It’s been 25 years since Macy Gray’s gravelly, one-of-a-kind voice first broke through the noise of pop music with her debut album On How Life Is.
In 1999, her enormous hit track I Try was already glinting with the gold of an all-time classic, even as it continued to dominate charts all over the world and propel her album to number one.
The 31-year-old single mother of three from Canton, Ohio, earned a Grammy for the song, and the sky seemed to be the limit from there.
But in the following quarter-century, despite continued success with her second and third albums, Gray earned a complex reputation, once famously forgetting the words to the Star-Spangled Banner and other similar mishaps. It began to look like she was standing in her own way.
Among journalists, her name became synonymous with diva tendencies and uncooperative interviews. As a result, the prospect of speaking with Gray as she prepares to celebrate the milestone anniversary of On How Life Is was more than a little daunting – especially given that she just this year stormed off reality show The Masked Singer, once again displaying a fiery temper to fans.
But when Gray sits down with Metro to discuss her upcoming new album, the legacy of her debut, and her past regrets, she’s unexpectedly softspoken and attentive – if not overly forthcoming at first.
‘I was listening to it the other day,’ Gray says of her breakout hit, I Try. ‘That song is on autopilot in my brain. It’s like walking and talking – you don’t even think about it anymore.’
While many artists grow weary of their most well-known work, Gray remains deeply connected to the record that changed her life: ‘People ask me if I’m tired of it, or if I’m over it… but I’m just not. I love that album, it helped change my life, and I still love performing it.’
For Gray, On How Life Is captures the essence of a transitional time, personally and universally. ‘It was that moment everybody has where you’re trying to grow up,’ she recalls.
‘You’re in your twenties, your mom and society are pressuring you, but you’re still figuring it out. You’re supposed to be the sh*t, but you’re not quite there yet.’ That honesty, paired with Gray’s signature voice and genre-bending style, has allowed the album to endure the test of time.
Contrary to her reputation, she seems more than willing to acknowledge her past mistakes, and one can’t help but wonder if her notoriety is entirely earned – or just the product of a sensitive, artistic spirit being thrust suddenly into a brutal spotlight.
When asked what advice she’d give her younger self, she sighs and admits: ‘I don’t know what I would tell me, because I know I was at a point in my life where you could have given me the best advice ever, and I probably wouldn’t have listened, you know?’
As for regrets about the last 25 years, Gray says there are ‘a million things’ she’d go back and change, and, when prompted to expand, she admits: ‘There’s always somebody that got away. Of course, you want to do smarter things with your money. I probably would have moved. I don’t think I would have stayed in Los Angeles. I probably… I had so many opportunities to live overseas and I blew them off. I probably would have moved, that’s one thing, somewhere else.’
She even seems willing to discuss her disastrous reality TV career, revealing light-heartedly that she turned down a stint on Celebrity Big Brother because: ‘They told me they only had one bathroom. I didn’t know if I could have made it through that.’
But not one to dwell unnecessarily, Gray is quick to assure that ‘her whole life has been a highlight,’ and for now, she’s looking towards the future.
‘I want to make more good records. I want to be a better singer, better on stage. I’m just focused on getting better, really,’ she says with real conviction. That dedication is the heart of the advice she’d pass on to rising artists: ‘Keep practicing. Keep getting better. Don’t forget how you got there.’
Her upcoming album will feature new collaborations, though she’s keeping names under wraps for now. She lights up at the mention of newer artists like Lola Young and Doechii, and it’s evident that Gray remains as passionate about her craft as ever, even if she sometimes finds it challenging to navigate the public relations side of things. ‘Doechii’s awesome – refreshing. I hadn’t thought about it, but yeah, I should reach out to her,’ she says.
Macy Gray UK tour dates
As she kicks off her UK anniversary tour, the 57-year-old is well aware how much people need music and escape; people are ‘just dying for an excuse to party.’ And she’s prepared to give it to them.
Her shows promise a full-throttle celebration: ‘We got the best music, and we’re gonna have fun—dancing, singing, screaming. It’s a good night out, a great show.’
The UK, Gray says, has always held a special place in her heart. ‘Every country, every city has its own personality, but the UK… they’re ready to celebrate. Almost on the edge of their seats, like just waiting for you to do something so they can just get up and go, you know?’
Her Glastonbury performance is still one of her most vivid career memories, and she’s quick to say she wouldn’t rule out an eventual return to Worthy Farm. ‘When we got to I Try, it was like this sea of people singing every word. You can’t get that feeling anywhere else.’
The traces of weary disinterest displayed through parts of the interview dissipate when she’s reminded of the time a naked couple streaked across the stage at her Glastonbury performance. One can’t help but think we’re getting a brief glimpse of the real Macy as she belly laughs at the memory.
‘So I was singing, and all of a sudden this – and they were older – like they were, like, skinny, you know, little bit wrinkly, and they just ran across the stage, butt naked, and they waved at me, and then they ran off,’ she says animatedly through laughter. ‘And that was it. I can see it, like, second by second. I don’t remember what I did. I was so stuck on them, I don’t remember if I stopped.’
When Gray really gets talking, her famous voice, with all its quirks, is on full display. Unkindly described in the past as ‘a cross between Minnie Mouse and Marge Simpson,’ it’s not surprising that it’s been a source of insecurity for the singer, given how much the media commented on it at the beginning of her career.
‘It’s true I used to be really quiet in public because people would laugh or have comments,’ she says of her voice. ‘That’s gone away a lot since I’ve gotten older, but sometimes I still kind of think twice before I say something.’
Her perspective on fame has also evolved. She notes how different the industry is now, especially with the rise of platforms like TikTok. ‘You can make a song and put it out the next day. That’s new. It’s great for the fans, but it’s a different world. I’m adjusting.’
Gray’s soulful, timeless music remains as relevant today as ever, but many of her inspirations and mentors have passed away, leaving her to navigate her evolution as an artist on her own. ‘I don’t think I would be making the music that I make had I not listened to everything Prince put out, you know.’
But the late legend was more than a source of musical inspiration to her: ‘We used to talk, and he was always giving me really good advice, you know, he always answered the phone, which I thought was super cool. But there’s a ton of influences. I’m a big Donna Summer fan. I got to spend some time with her, and I learned a lot from her.’
Despite all the changes, Gray sees music and entertainment as a unifying force, even as the world grows more fractured. ‘You go to a festival, and you’re not thinking about who voted for who. Everybody’s singing the same song, dancing together. Entertainment is essential right now.’
At 25 years since her debut, Macy Gray isn’t slowing down or apologising unnecessarily for the times she’s stumbled. She’s still experimenting, still growing, still trying her best to weather a harsh industry with a sensitive disposition and a wide-open heart. That may not always be pretty, but for Macy Gray, you can be certain that it will always be authentic.
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