On How Life Is by Macy Gray (1999)
#5
A wise, soulful R&B debut that plays out like an early Fiona Apple record if she had been about a decade older and even more world-weary in 1999. With a neo-soul palette that draws from facets of black music from funk to R&B to hip hop to gospel, Macy Gray sings about all sorts of life experiences with her distinct, raspy voice. The album that results is incredibly realized and mature, and also extremely catchy.
There really is a song on this album for nearly every human emotion. “Caligula” and “Sex-o-matic Venus Freak” are groovy and sexual, while “I Try” and “Still” are melancholic songs about mourning lost love and unhealthy relationships. Elsewhere, “I’ve Committed A Murder” fantasizes about murder, while “I Can’t Wait to Meetchu” fantasizes about dying and reaching the afterlife. All the while, Macy Gray’s emotive singing and the record’s bombastic, genre-defying instrumentals and larger-than-life choruses make it an unforgettable listen.