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Talking With Macy Gray About Taking Her Breakthrough Hit Back On The Road

“I just made a record that was from my heart and I was really pleasantly surprised when so many people liked and responded to it,” remembers Macy Gray. “I was really shocked by the success of ‘I Try,’ ‘cause I didn’t think that was a hit at all.”

It was 2000, the same year as R&B smash “Say My Name” by Destiny’s Child and country singer Faith Hill’s crossover ballad “Breathe.” It marked the rise of Detroit rapper Eminem and solidified the dominance of Christian alt-rockers Creed.

Of all the one hit wonders that year—among them Sisqó with the prurient “Thong Song” and Alice DeeJay with some happily forgotten Eurodance earworm—Gray stood out, and not merely because she won a Grammy for her performance on her breakout hit “I Try.”

Her gravelly voice, the retro-yet-modern production, and her rags-to-riches discovery story (she had been living at home with her mother in Canton, Ohio, when she was signed to Epic Records) lent Gray an air of authenticity that seemed lacking in an industry where boy bands proliferated and alternative rock was actually mainstream.

Fourteen years later, Gray is once again taking her 1999 debut album, “On How Life Is,” on the road. With the Millennials now in their 20s and 30s and ripe for nostalgic revisits to adolescence, Gray’s timing is canny, particularly since she is at work on a new album intended for release in 2014. She will appear at the Sinclair in Cambridge on Nov. 15.

When talking about her inspiration for the tour, though, she remembers going to a festival and seeing Lauryn Hill and A Tribe Called Quest perform their first albums live. “Everyone lost their minds,” she recalls fondly.

Of the songs on “On How Life Is,” Gray, 44, says, “They’re still catchy. I think they still have meaning. A lot of the fans that show up remember that album as a part of whatever they were going through at the time. So it’s just dope, and having people remember every single song from 14 years ago is amazing.”

The story is almost as good as the album itself. Gray, born Natalie McIntyre, stumbled into singing accidentally, when she was in college and writing songs with her boyfriend. When their friend, a vocalist, failed to show up for demo recording sessions, Gray would sing the parts herself. A few years later, she was signed to Atlantic only to get dropped, and had moved home to Ohio from Los Angeles, pregnant, in the midst of a divorce, when she got the call from Epic.

“It was a shock, because I had that experience with Atlantic where I got my hopes up and nothing happened. I think that was the beauty of it, when I did the “How Life Is” album, it wasn’t that I wasn’t expecting anything, but I wasn’t like, ‘This shit is gonna blow up and be so dope.’”

“I Try” is a catchy enough soul-pop anthem, but Gray’s voice carries it. There is a reason she is sometimes compared to the Cookie Monster, with more phlegm to her delivery than any sound conceivably produced by a vocal cord. But there was something about that peculiar rasp that people connected with at the turn of the Millennium; “On How Life Is” was certified triple platinum in the US, and Gray was nominated for five Grammys.

This success, however, proved impossible to repeat. Gray’s second offering, “The Id,” drew respectable sales but suffered from its unfortunate release date, just a week after the Sept. 11 attacks. Meanwhile, Gray was making headlines with the sort of diva-ish shenanigans that become the stuff of industry legend: she was booed by an audience in Canton for forgetting the words to the national anthem and reportedly stormed out of a photo shoot for “Vogue.” Her third album, “The Trouble With Being Myself,” bombed, and it was four years before she began making records again, with each successive album selling worse than the last.

Talking to her now, though, you get the sense that the drama is long behind her. Speaking over the phone from Los Angeles, where she lives, she sounds gentler than on the recordings, and is thoughtful and gracious, if a little guarded.

That’s not to say that there’s nothing of the diva left in her. Gray is fond of sparkly gowns and wild hairdos, and possesses an offbeat, effortless presence, striding across the stage with her catlike eyes half-shut. As a singer of limited range, she wisely relies on the talents of her backup band to carry the show. Yet her voice, which could easily be written off as mere shtick, is reliably riveting, and she exploits its eccentricities, milking every gargle and croak.

She seems to have gained more confidence even as her career has mellowed. Her last two albums contain no original material, despite the prevailing wisdom that cover records don’t sell: “Talking Book,” a remake of Stevie Wonder’s iconic 1972 album, and “Covered,” which touches on a surprising collection of pop acts both new and old, from Arcade Fire to the Eurythmics.

“They were songs that were close to my heart and meant something to me,” Gray says of the album. “And it was something that I always wanted to do, but the label was against it.”

As for her career going forward, Gray talks not in terms of record sales or influence, but emphasizes quality and expresses appreciation for her fans. Yet the glow of that early success is still detectable in even her humblest remarks, like the fading trail of a meteor as it arcs towards the earth.

“I really want to make awesome records for people, you know,” she says. “I really want to make great records and make things that move people and that touch people and that people want to sing over and over again.”

This article was originally published on November 08, 2013.

This program aired on November 8, 2013. The audio for this program is not available.

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