Macy Gray - On How Life Is (1999)

Macy Gray is such an assured, original vocalist that it's hard to believe On How Life Is is her debut album. She recalls a number of other vocalists, particularly jazz singers like Billie Holiday and Nina Simone, but she is unquestionably from the post-hip-hop generation, which is evident not just from the sound of the record, but the style of her songwriting, which is adventurous and unpredictable. Thankfully, she's worked with a producer (Andrew Slater, who pulled a similar trick with Fiona Apple's debut, Tidal) that lets her run wild and helps her find sounds that match her ideas. That's not to say that On How Life Is is a perfect album -- at times, Gray attempts more than she can achieve -- but it's always captivating, even during its stumbles. And when it works, it soars higher than most contemporary R&B. © Stephen Thomas Erlewine /TiVo