Macy Gray skyrocketed to stardom at the turn of the millennium, making a massive breakthrough with her debut album On How Life Is in 1999. The album spawned the massive Top Five single “I Try,” bringing Gray into the mainstream and earning her the Grammy Award for Best Female Pop Vocal Performance and multiple platinum certifications. Gray would go on to build a highly successful career, producing gutsy original material and bold covers paying tribute to her influences and favorite artists like Stevie Wonder, Nina Simone, and Metallica. Over the years, she has earned four more Grammy nominations and released a total of ten studio albums, including 2016’s Stripped which marked a change in direction for the artist, featuring covers of her original hits recorded as jazz. In 2018 she returned with new original material on Ruby, proving she wasn’t content with living strictly in the past.