Ask the funky R&B-pop singer Macy Gray why she named her new album Ruby and you don’t get a standard answer about her favorite color. “Red represents passion and going crazy and stop signs and all that,” Gray says. “Ruby is the color you get to right before you get to red, that moment before you go nuts.”

She should know. Her career’s been a red-lit roller coaster during the two decades since her 1999 debut On How Life Is yielded “I Try,” which hit No. 1 while the Ohio native was touring in Europe. “It was my first time on tour, my boyfriend was in the band, I was [around] my 20s, and I was just partying,” says Gray, 51. “I was on this little rainbow cloud. I was happy that [the song] broke but mostly I was so busy having a good time, I didn’t even realize what was really happening.”

Her party-fueled fame train slid off the rails within a few years as Gray lost her mainstream momentum. She’s made several albums since, last indulging in her early love of jazz for 2016’s Stripped, but Ruby stands as her pop comeback, a genre-refracting gem with guest turns from Meghan Trainor and Gary Clark Jr.

“I just kind of hit the lottery,” says Gray, who clicked with producer/songwriters including Tommy Brown (who worked on Ariana Grande’s “Leave Me Lonely,” which featured Gray in a cameo) and Johan Carlsson. “We wanted to do Nina Simone 2020,” Gray says, “but you know, everybody’s who they are, and that’s what we came up with.”

The album slides from cheery pop to seductive reggae to heady thumper “White Man,” inspired by prejudice in President Trump’s America. “He’s stuck way back,” she says. “But again, it’s optimistic ’cause I say ‘Let’s make it better, let’s come together.’ ”

Nantucket native and fellow Grammy winner Trainor came by the studio to see Brown and ended up co-writing “Sugar Daddy” and adding a backup vocal. “She’s a sweetheart,” Gray says. “She has this huge career, but she’s just a kid still.”

Record labels gravitate to young artists today, Gray says from her LA home. “I didn’t want to be one of those older artists trying to sound young. … That put me in a situation where I wasn’t as successful as other artists commercially, but I couldn’t do it. I actually tried a couple of times, but I just felt so stupid. Music is all timing, and there’s always a space. You just have to find yours and make it work.”

That includes her trademark raspy voice. “When I was coming up, Mariah Carey and Whitney Houston were like everything, and I couldn’t sing like that,” Gray says. Her tastes ranged from Prince and Diana Ross to Led Zeppelin and Guns N’ Roses. “Probably the person who influenced my singing most was Billie Holiday because my first bands were jazz,” she says. “When I first started out, I did everything she did. She had this way of getting her lyrics across without belting.”

Gray projected a visual persona with her spiky Afro and colorful outfits. “I forget [who] said, ‘You don’t want to get onstage and have somebody say, “Oh, I have that same shirt,” or “Oh, she got that at H&M,’ ” she says. “So I always got my clothes made and I like color because I noticed everybody got onstage in black. … I didn’t want to look like everybody else.”

Born Natalie McIntyre, she found her future stage name as a child, falling from a bike near a mailbox labeled Macy Gray. She’s made much more of a name for herself than that old neighbor—and hits City Winery with a horn-spiced septet on Dec. 22, just days before Christmas. Reminded of this—and that perhaps she’ll dust off one of the holiday songs she’s recorded—Gray muses, “I should, huh?”

“I Try” poses more of a sure bet. “Everybody’s still so excited when we play that,” she says. “It’s going on 20 years, and they still know it word for word. I don’t even have to sing a note. It’s crazy.” With a shade of red. ◆

Macy Gray plays City Winery on Dec. 22.

For more music coverage, check out Paul’s Weekend Music Ideas.