When singer Macy Gray released her song “I Try” in 1999, she doubted its potential as a hit record.
“I thought the chorus was too wordy,” Gray says. “I thought it was too slow.”
Featured on her debut album “On How Life Is,” the heartbreak ballad became her breakout hit. It skyrocketed to the top of the charts, peaking at No. 5 on the Billboard Hot 100 and earning Gray the Best Female Pop Vocal Performance at the 2001 Grammy Awards.
Twenty-five years later, Gray celebrates the release of her first album with an anniversary tour and makes a stop in ӣƵ for a performance on July 25.
The Ohio native says the set will be full of “singing, dancing and screaming” as she and her band run through the “On How Life Is” album in its entirety. Following a support set from ӣƵ-based band the Playadors, Gray intends to dive deep into the album that introduced her to a generation of new fans at the turn of the century. She plans to stir up memories and smiles with her nostalgic tunes.
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Macy Gray
“Everybody leaves with a smile on their face,” she says. “I’m just going in there to make people happy. It’s the best job ever.”
Gray’s life was a blend of smiles, heartache and change when she recorded her 10-track album debut. She was 28 years old and recently divorced, navigating motherhood as she pursued her career in music. Her experiences radiated through her songs’ lyrics. “I Try” dives deep into the duality of balancing ending a relationship with one’s self-worth, while “A Moment to Myself” describes the relief attached to escaping a life of struggle as a 20-something.
“I think late 20s is like a big fork for everybody. It’s kind of like ‘What am I going to do next?’” she says.
Although she didn’t know what was next for her then, it was certain that writing and storytelling would be a part of her future. Writing was always a part of her life.
“A lot of times you don’t even know how you feel until you start writing,” she says. “I think writing has saved my life.”
Her stage name was originally a fictional character in her school writing assignments, stolen from the nameplate on the side of a mailbox she’d crashed her bicycle into as a kid. She says the name was “nursery-rhymey,” something she could hold onto as a child and use in her creative writing. Her real name is Natalie Renée McIntyre, but stage names were all the rage when she kicked off her singing career, and Macy Gray was the perfect performance pseudonym.
The storytelling trickled down into her songwriting. Tracks like “I’ve Committed Murder,” “Still” and “The Letter” take listeners on detailed journeys as they explore the honest and vulnerable tales hidden in the lyrics of “On How Life Is.”
Her strides as a creative and storyteller continued as she released 10 studio albums in the decades following her debut and into her career as an actress, as she brought characters to life in films like “Training Day” alongside Denzel Washington and in Tyler Perry’s “For Colored Girls.”
Gray’s music has remained relatable throughout the years. Her 2023 album, “The Reset” was recorded during the pandemic with her band, the California Jet Club. She says they had to wear masks and plastic over their shoes while recording because “it was new, and people thought you could pick up COVID off the streets from your shoes.”
No one could stop thinking about COVID, and the only certain thing was that unknown times were ahead. Gray remembers everyone using excessive amounts of hand sanitizer as they created a 13-track protest album describing the present political climate.

Macy Gray performs in front of a projection of Brazilian singer Elza Soares, at the Rock in Rio music festival in Rio de Janeiro, Brazil, Sunday, Sept. 11, 2022.
The Grammy Award-winning singer is currently focused on new music, beginning with covering a few of her favorite songs. She released a cover of the Alicia Keys song “No One,” bringing acoustic melodies and jazzy vocals to the 2007 hit record. She’ll also be reimagining “I Try” with the band, bringing a fresh perspective to the songs that captivated listeners 25 summers ago.
“It’s exciting to get feedback, see what people think, and see what people are reacting to these days,” she says. “It’s cool.”
Being a fan of music inspired her to toy around with cover tracks before releasing more original material. She knows the industry is different now, and the goal post for success has moved. While growing up, artists wanted to play stadiums and arenas; however, Gray says new artists have goals more centered around social media metrics like followers and views.
“It’s just kind of gone downhill, and that’s no offense to the artists who are out now,” she says. “It’s just different.”
Despite the changing tides, Gray remains steadfast in her creative strides as a writer and musician. She knows she’d rather write things down than say them aloud on most days, and that the music business is “unrecognizable” to her. Still, she hopes her music makes people feel something and that she is remembered as someone who had great things to say.
“Nobody wants to be forgotten,” she says. “I hope my music lasts.”