Macy Gray says her naked Glastonbury stage crashers are still a career highlight

‘It was that moment everybody has where you're trying to grow up.'

Macy Gray says her naked Glastonbury stage crashers are still a career highlight
A quarter-century after her hit debut album, Macy Gray opens up about her legacy, future, and that crazy Glastonbury moment (Picture: Getty)

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.

The singer says she’s still not tired of performing I Try live (Picture: KMazur/WireImage) The debut album went to the top of the charts all over the world (Picture: C.D COVER) Despite earning a complex reputation, Gray comes across softspoken and calm (Picture: J. Vespa/WireImage)

‘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?’

Gray won a Grammy in 2001 and has been nominated five times (Picture: Christie Goodwin/Redferns via Getty Images) Pictured here with Paul McCartney, Gray is remembered among the most successful musicians of the last 25 years (Picture: KMazur/WireImage) Even icons like David Bowie took notice of the high level of artistry on her debut album (Picture: Arun Nevader/FilmMagic) Gray sites Donna Summer, Prince, Billie Holiday, and Stevie Wonder among her musical inspirations (Picture: Jeff Kravitz/FilmMagic, Inc)

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.’