Macy Gray, shown here in 2023 in Milan, Italy. (Photo by Francesco Prandoni/Getty Images)Getty ImagesDo you know Macy Gray? I mean, you undoubtedly know the song “I Try,” her first and biggest hit, from 1999, which became the anthem of the Y2K years and lifted her out of obscurity to become a Grammy winner and one of the least likely pop stars of her era. Hers is a sound that leans on a trademark raspiness of sweetness and grit — “like honey with the stingers left in,” as a critic for The New Yorker once wrote.But do you know her? I thought about that last night at Blue Note in Los Angeles, where she played with a group of six talented musicians in poofy blonde wigs that still weren’t quite as dramatic as Macy’s own famous ‘do. Where’s she been? What’s she been up to? What’s coming next? Macy Gray’s Ricochet Ride To Success I met her once in Malibu, right at the very start, for a magazine profile, when the first album was on every radio in America and she seemed faintly astonished to be attached to any of it. I remember she pulled up in a Mercedes G-Wagon, came out in chunky heels (even though she’s already six feet tall) and spent the next hour being almost painfully shy — laughing at her own answers before she’d finished them, folding herself into the furniture. She had the look of someone who had been handed a winning lottery ticket and told it was hers to keep. The high, strange, sandpapered voice had been a blessing and a curse. Growing up in Canton, Ohio, it was what got her teased. She has said she didn’t really learn how to hold a conversation until she was about ten. Later, she went to USC to study screenwriting, not music. While she was there, she started writing lyrics for friends, and when a singer failed to show up for a demo session, Gray stepped in and sang the song herself. People responded (how could they not?), and she gradually moved into live gigs, songwriting and eventually a record deal.Her personal life was moving just as quickly. She married mortgage broker Tracey Hinds, had two children in 1995, and was pregnant with their third when the marriage fell apart. Around the same time, Atlantic shelved her album and dropped her, and Gray returned to Ohio with her children, assuming her music career was probably over. For a while she was typing college students’ papers while pursuing a teaching credential. Macy Gray’s Turnaround MomentBack in the day with Macy Gray at the 42nd annual Grammy Awards nominations in 1999.Getty ImagesThen a Los Angeles music executive named Jeff Blue heard Gray’s unreleased Atlantic recordings and tracked her down in Ohio. He persuaded her to give music another shot, signed her to a development deal and helped her make a new batch of songs drawn from everything she had just been through. To get labels to listen without being scared off by her failed Atlantic deal, Blue even circulated the demos under the name “Mushroom.” Epic Records bit, signing Gray in 1998.Her debut album, On How Life Is, came out the following year and was slow to catch on. Then its second single, “I Try,” took off, eventually reaching No. 5 in the U.S. and turning the 30-something single mother into an international star. Twenty seven years on, even the youngest servers at the Blue Note know all the words as they drop off drinks at the tables. A Night In Full Joy Mode With Macy GrayLast night Gray was in joy mode or maybe even F-it mode. She informed us the band had driven “all the way from Tarzana” to sing us some Macy Gray songs and that we had better dance. She stopped a singalong to let a table of wildly enthusiastic women know they were welcome to try that again, this time on the beat. She told us the world is a beautiful place. She told us the world is a crazy s-hole. At 58, the voice has more weather in it now — it’s lower, sanded further down, less honey and more stinger. What’s gone is the flinch. She seems okay with where she is and what she’s done, and it’s been a lot. There were the acting gigs in Training Day and one of the Spider-Man movies. There was a song-for-song remake of Stevie Wonder’s Talking Book in 2012 (it’s amazing if you haven’t heard it), cut for the album’s fortieth anniversary. There was Stripped in 2016, recorded in an old Brooklyn church, live, with one mic. And then, because why not, three separate turns on The Masked Singer on three continents. For the rest of 2026, Gray will be singing and charming her way around Australia and New Zealand before heading into Europe. This fall she’s got a new album coming out called “The Trouble With Truth.”Do I know Macy Gray? Not remotely, even now. But I was happy to see her looking so happy last night at the Blue Note and enjoying the moment. She tried to say goodbye once and choked. She definitely seems to have gotten over that.Also From ForbesForbesThe Museum That Charges You $129 To Read Your HeartbeatBy David HochmanForbesThe Ultimate Los Angeles Date Night—A Tablecloth And 18,000 StrangersBy David HochmanForbesSkip Japan’s Tourist Circuit And Walk These Ancient TrailsBy David Hochman