Macy Gray On Living Without Regrets & How Nicole Kidman Made Her A Better Singer

The US R&B and soul superstar Macy Gray no longer wallows in regret. "You look back, and you say, 'I wish I would have done that' or 'What if I would have said that?' and 'What if I didn't say that?'" she ponders. "But that is the road to insanity; you'll just drive yourself crazy – 'cause you can't go back."

Instead, Gray is learning from experience, commending Dale Carnegie's enduring self-help tome, How To Win Friends And Influence People. "It really mentally helped me just stop beating myself up for things that I missed." Gray has fathomed that, while she can't alter her past, it's possible to shape the future—which is "empowering."

Ironically, Gray is journeying back to the '90s for her latest undertaking. The zany vocalist will head out on the road to mark the 25th anniversary of her classic debut, On How Life Is – released in July 1999 and showcasing her bluesy signature, I Try (an Australian #1). 

Gray has a long relationship with Australia, initially touring in 2000 and most recently in 2015. "I remember the first time I went—the first thing we did was go to the zoo 'cause we wanted to look at kangaroos," she says from her base in suburban Los Angeles. So I always have that memory—the zoo."

Gray collaborated with Melbourne DJ/producer Kaz James on his 2000s electro-pop single Can't Hold Back, and, in 2021, she competed on The Masked Singer Australia. What keeps her returning? "The beaches and the men are good-looking – and it's just fun."

Gray (real name Natalie McIntyre) broke out at the tail end of the '90s' neo-soul movement led by Meshell Ndegeocello, D'Angelo, Maxwell, Erykah Badu and Lauryn Hill.

As a child in Canton, Ohio, Gray was bullied over her distinctive voice. Later, attending college in California, she joined a music community. Gray realised that she could sing and fronted a jazz band. Gray was compared to Billie Holiday. 

Gray had professional setbacks early on. She demoed material alongside local producer Joe Solo, securing a contract with Atlantic Records, only to be let go after a key A&R executive left. Gray had virtually quit the business when she was offered another shot at Epic.

"My first time didn't work out. I was dropped by Atlantic – which was probably one of the best things to happen in my career because, when I got into the Epic record, I wasn't expecting anything." Meanwhile, Gray guested on The Black Eyed Peas' buzz breakthrough, Behind The Front.

Gray would team up with Andrew Slater, a music journalist turned manager and producer. He'd previously worked on The Wallflowers' eponymous debut and Fiona Apple's Tidal. 

Gray shares that in the beginning, the pair disagreed on a musical direction. "[Slater] had a whole different vision of what [he] wanted to do than I did. He wanted to do an R&B record with live instruments. So it was an R&B record, but it had a rock and roll nuance, the way you make rock records.

"I was just so not down – I wanted to do it my way. So we had this little push and pull for a minute. 

"But he won… We had this huge studio at Sunset Sound [Recorders in Hollywood], and we had all these crazy instruments that I had never seen before. So I was kind of so in awe of what he created that I got over myself."

Behind the scenes, Gray had to contend with domestic upheaval. "It was a wild time," she recalls. "I was in the middle of a divorce. I had three babies. My youngest was only about one when I went into the studio. I had my cousin out [in LA] – he was watching my kids while I went to the studio, but that wasn't going well. So I started bringing my three babies to the studio while I was making the record!"

Even at Epic, Gray didn't saviour immediate gratification. Her first single, Do Something, sampling OutKast, faltered. Yet Gray's fortunes changed when I Try was serviced to radio months after the album release (with a cult remix by the feted J Dilla for the heads).

The sleeper success of On How Life Is caught Gray off-guard – the album accumulated multi-platinum sales in the US alone. "I was kind of used to me doing things, and it wouldn't work out. So I went in totally free of all that expectation and wanting to make a hit and all that. I just was really enjoying making an album and meeting all these cool new musicians and writing songs. It was like Disneyland, you know?"

Gray was nominated for five Grammys, including Song and Record Of The Year. The singer took home the award for Best Female Pop Vocal Performance with I Try – which is "right in plain view" as she speaks. 

"My problem is I didn't think the Grammys were a big deal 'cause, when I was a kid, I always watched the Grammys, and they were always super long and super boring," Gray admits. "So, when I got a Grammy, I really didn't understand what had just happened to me. I mean, I knew it was cool to have one, but I didn't realise 'til maybe five years ago that a Grammy was really a huge deal."

Gray laughs at the idea that her old Atlantic associates must have been seething over the response to On How Life Is. "A lot of people were. Everybody told me 'No'. So trust me… All of them told me 'No' before that record came out."

However, Gray then felt pressured to match that achievement with her sophomore, the id. "It's not even [coming from] you; it's your label," she says. "They have a really big success with you, and, of course, they want that to keep going—because their lives change too. They get promotions and they get points, so it's really important for them that you keep that up."

In fact, Gray hoped to venture out stylistically but encountered resistance. "Me, for myself, I just wanted to make records, and I just wanted to make art – I just wanted to make cool stuff. 

"I wanted to do a heavy metal album, and they talked me out of that really fast! I wanted to do a jazz album, and they were like, 'No, everybody will think you're finished. That's [for] when you turn 60; that's when you start doing jazz.'"

On the id, Gray introduced more hip-hop influences, liaising with Raphael Saadiq and The Roots' Questlove plus inviting Badu (another Holiday soundalike) to feature. Though credible, the album didn't sell as spectacularly.

In the interim, Gray struggled with celebrity – compounded by personal challenges. In 2014, she opened up on Oprah Winfrey's Where Are They Now? about past alcohol and drug dependency. Gray has also discussed her bipolar disorder. 

Today, Gray has greater insight into industry machinations – and "the real world." "But that [advice] in my ear really, really messed me up," she confides. "I was really confused. I kind of lost my way for a while. I couldn't give [the label] what they wanted – 'cause that wasn't what I set out to do." Gray finally became independent in the 2010s. 

Gray contributed Time Of My Life to Eminem's best-selling 8 Mile soundtrack – and she has diversified into acting, making her silver screen premiere in the Denzel Washington vehicle Training Day. "I love it! It's a whole different craft. I can sing in my sleep, but acting, I'm still learning, and I still have to really try."

Gray was cast as the waitress and narrator in Lee Daniels' 2012 The Paperboy – his first film following the acclaimed Precious. 

Observing the Aussie Oscar-winner Nicole Kidman on set, Gray contemplated her own progress, albeit musically. "She had her acting coach on set, and she had a dialect coach. They were with her every step of the way. She reminded me that I can still get better. 

"At the time, I think I was kind of feeling myself. But she got me back on track. I started seeing my vocal coach again.

"I'm sitting there like, 'If she's still working on it, then I should definitely get back to the books.' So she actually, in the weirdest way, made me a better singer – 'cause I started really practising again."

In 2016, Gray was a surprise guest on Ariana Grande's Dangerous Woman with the '60s-inspired duet Leave Me Lonely – and she found herself embraced by Arianators online. "It was definitely a lot of kids commenting," Gray chuckles. "I think a lot of them thought that I was new and that she discovered me and was boosting my career."

Gray was "shocked" that the track wasn't selected as a single "because that song was amazing," she declares. "But it did really well. It was one of the most streamed songs on that album."

Last year, Gray delivered her 11th album, The Reset, with her band, The California Jet Club. The album included the single Thinking Of You and a bold, if cruisy, cover of Body Count's infamous Cop Killer. 

Now Gray is promoting a percussive collab, I AM, with New Orleans' Queen Of Bounce Big Freedia. They previewed it live at LA's LGBTQIA+ fest OUTLOUD in early June, with the star lauding it as "one of the best songs I've ever heard."

She's sitting on another track penned by friend Sharon Stone (yes, of Basic Instinct fame) entitled Tuesdays. Gray plans to add both to a "deluxe" edition of The Reset.

The timing is auspicious with Gray launching a world tour – the first stop is the Festival Of Voices in nipaluna/Hobart. She'll perform On How Life Is in its entirety, as well as other cuts. "Oh, we're gonna have a ball," Gray enthuses. "We're gonna play new songs. We're gonna totally rock out on the debut album, celebrate the 25th anniversary…

"It's still around, you know. The other day I'm at the gas station and they're playing I Try!

"We're just gonna celebrate. It's gonna be an excellent night. 

"I have the greatest band ever – and I'm not so bad myself. So we're just gonna have a good time, really."

Macy Gray will celebrate the 25th anniversary of ‘On How Life Is’ with an Australian tour this July. You can find tickets here.

MACY GRAY

‘ON HOW LIFE IS’ 25TH ANNIVERSARY

2024 AUSTRALIAN TOUR

Wednesday July 3 – Hobart, Odeon Theatre (Festival Of Voices)
Thursday July 4 – Adelaide, Hindley Street Music Hall
Saturday July 6 – Brisbane, Fortitude Music Hall
Sunday July 7 – Melbourne, Hamer Hall
Tuesday July 9 – Gold Coast, Star Theatre
Wednesday July 10 – Wyong, The Arthouse
Thursday July 11 – Canberra, The Playhouse
Friday July 12 – Thirroul, Anita’s Theatre
Saturday July 13 – Sydney, Enmore Theatre