That's not to say there haven't been personal challenges. But when it comes to the music, Gray says she's flown with the headwinds for two decades, from the moment she recorded the album that would make her a Grammy-winning star, and even earlier, when she was playing in bands and singing at jazz bars in college as a hobby.
"I never really planned out my career like I see some of my friends do," she tells New Times. "Of course, I wanted to be around for 20 years, but I didn't plan it or organize it."
That lack of rigid direction has largely worked in Gray's favor, particularly when it came to putting together her debut album, 1999's On How Life Is. That record spawned the unforgettable hit single "I Try," but Gray says the song the world came to love is much different from the one she originally envisioned. Her producer at the time, Andrew Slater, worked with artists such as Fiona Apple and the Wallflowers, so he brought a pop/rock production style to a song that began as a bass-heavy composition with a hip-hop backbeat. "I fought about it a lot," she remembers. "I didn't want it to change, but... he ended up being right."
Though Gray acknowledges her collaborators ultimately made the right call, she also remembers some of her ideas being dismissed during those album sessions because she was a new artist. After she became a household name, her subsequent albums included collaborations with artists as diverse as will.i.am, John Frusciante, Erykah Badu, and Justin Timberlake. And her latest album, Ruby, finds her toying with the blend of hip-hop, jazz, and funk that's resulted from decades of musical experimentation. The
"The drummer that played on this album the most is a terrible drummer, but the way he plays works for the record."
While some songs on Ruby employ electronic elements — "Sugar Daddy," for example, is driven by a trap beat — most of the album feels as if it was crafted at one of those pre-fame jam sessions but fronted by a singer with decades of experience.
"I've just been around long enough to know who does what," Gray says. "On this record,
It's this freewheeling approach that keeps Gray confident when she's approached for collaborations with ensembles such as Nu Deco. The rotating nature of the ensemble's collaborations allows for limited rehearsal time with guest artists. Gray won't be able to practice with the band until the day before the Arsht Center concert. "I don't have to rehearse a lot, really. The band does, 'cause they're 50 people and they've got to figure it out. But me, on my own, I can come in once or twice," she says.
Gray is comfortable with the process because she takes a similar approach in the studio, laying down only a handful of takes before producers take the reins on the tracks. "I'm just at a level [where] I don't have to do something over and over again," she says. "My producer told me he was working with one artist — I won't say her name — but she spent like three months on one vocal. That's absurd. That's crazy! I mean, oh my God, she could've written a book!"
Macy Gray. With Nu Deco Ensemble, BJ the Chicago Kid, and the Miami Mass Choir. 8 p.m. Saturday, December 15, at the Adrienne Arsht Center for the Performing Arts, 1300 Biscayne Blvd., Miami; 305-949-6722; arshtcenter.org. Tickets cost $25 to $80.