Macy Gray brings her R&B, jazz-inflected pop to Detroit Jazz Fest 

"I love that song. People always ask me if I get sick of it, but I don't," says Macy Gray. She is speaking, of course, about her 1999 hit, "I Try."

According to her, no one was more shocked about that song's success than she was. "When we're on tour, as soon as I sing it, I don't have to sing but one word, the crowd just goes," she says. "Thousands of people still know every word, 20 years later. I had no idea that song — it was the No. 1 song for four weeks — I had no idea it was gonna be that. It's been a big surprise to me. So whenever I have to do it, I'm cool with it."

Gray is cool with a lot of things — she couldn't have asked for a life that suits her more than that of music. "I lucked out finding something I'm really comfortable with and really have fun doing all the time," she says. For someone two decades into her career, it means even more to still be having so much fun.

Though the singer-songwriter will always be best known for that hit single, she has a long and colorful musical history, releasing 10 studio albums and receiving five Grammy Award nominations in the process. (And one win, for Best Female Pop Vocal Performance. You can guess which song that was.)

Gray's style has always been in the R&B mode, augmented with neo-soul stylings and often entering pop territory, but she is actually quite versed in jazz as well, influenced in equal measure by Billie Holiday, Sarah Vaughan, and even Frank Sinatra.

While studying at the University of Southern California, she began singing standards with a band. "When you do covers, you gotta learn Frank Sinatra, Nat King Cole, and all that stuff," she says. "I'm actually an undercover jazz singer. But I love pop music and I write pop music better than I write jazz, so people think I'm a pop singer. But I really am a jazz musician when it gets down to it. When I'm totally comfortable and doing my thing, it's probably more jazz singing than mainstream."

Chris Collins, the Detroit Jazz Festival's president and artistic director, certainly knows this to be true. "When you hear Macy sing, it doesn't matter if she's singing pop or anything in between, a uniquely identifiable sound is there, a character, an interpretive skill that is really powerful," he says.

"Then, when I had a chance to hear her do a jazz set, she did some Duke Ellington ballads and, man, I was overwhelmed," Collins recalls. "Her understanding of that music and then the application of her own unique style really won me over, and I've been a huge fan." He brought her to the festival a few years ago, in fact, but it was one of those wild nights in which a veritable typhoon swept through downtown Detroit. The show could not go on then, so it's extra special that Gray is back now, for the festival's 40th iteration.

Born and raised in Canton, Ohio — a mere four-hour drive from our fair city — Gray actually spent about four childhood summers right here in Detroit. "My parents, and all my aunts and uncles, they shipped the kids out to Detroit," she says. "I never knew why, but we all went to my Aunt Hattie's house. She had 12 of us running around. We used to play baseball in the street and she cooked every day." Though she was too young to truly explore the city, it makes for a memory that gives her presence at the Detroit Jazz Fest a tiny flair of the hometown sensibility that is the festival's hallmark.

Gray says Canton was a great place to grow up — she says she is really proud to be from Ohio, and says she is "very Midwest" — and that she learned a lot there, but like many other Midwestern kids with big dreams, Gray knew she had to seek them elsewhere. "If you want to be an astronaut or a big-time football player, it's just not going to happen in Canton," she says. "There were things I wanted to do and things I wanted to see that I just couldn't see there."

Some of the things she would end up seeing were totally unexpected in a different way than one might imagine. She recalls one of the most amazing sights of her touring life at her first big music festival, the UK-based Glastonbury: "I'm on stage, and this couple, they had to be in their late 70s or 80s, they snuck up on stage naked and ran across my stage while I was singing," she says. "I'll never forget that. It was like I was dreaming or something."

Though that's unlikely to repeat itself at Jazz Fest, you never know. What can be expected at the festival is a great performance from Gray and her longtime backing band. "I have the best musicians in the world," she says. "They're all best friends, and it translates on stage. They're all really gifted musicians and we've got the songs, we've got everything going for us." Those songs are sure to include the hit that made her a household name, as well as tunes from her latest album, last year's joyfully jazzy, soulful Ruby, out on Mack Avenue Records.

So what's next for Gray? "I'd like to visit the moon." Wouldn't we all? On a more serious note, she adds," I'd like to get my own jet one day because I hate the airport. There's a lot of stuff I want to do, but I'm not sure in what order. I'll get it all done." At the very least, we know she'll try.

Macy Gray performs at 6 p.m. on Saturday, Aug. 31 at the JPMorgan Chase Main Stage at the Detroit Jazz Festival. The festival takes place Aug. 30-Sept. 2 across four stages in Hart Plaza and Campus Martius in downtown Detroit; 313-469-6564; detroitjazzfest.org. Admission is free.

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