Macy Gray parlayed an utterly unique voice and an outlandish sense of style into pop stardom at the turn of the millennium, appealing to audiences of all colors in search of a fresh alternative to mainstream R&B. After an accidental entry into the music industry, she reached the mainstream in grand style with "I Try," a Top Five pop hit in 1999. A Grammy award for Best Female Pop Vocal Performance, and multiple platinum certifications for the parent album, On How Life Is, followed shortly thereafter. Gray went on to build a sizeable and unpredictable discography that included gutsy original material and bold covers that paid tribute to Stevie Wonder, Nina Simone and Metallica. By 2016, she was revisiting career highlights with a jazz quartet, as documented on Stripped, but Ruby, issued two years later, affirmed that she wasn't content to live strictly in the past
