The college singer-songwriter aesthetic usually only goes so far, but Tracy Chapman has managed to make a multiplatinum-selling career out of accessible crooning and heart-wrenching lyrics. The Cleveland native began playing guitar at 11 before making her way to Boston, where she studied at Tufts and navigated the local coffeehouse scene. Unlike so many of her perennially "up-and-coming" peers, Chapman's ascendancy was swift and well-deserved—her 1988 eponymous debut was immediately heralded for its raw soulfulness and fresh-voiced rock. Since then, Chapman has earned four Grammys and churned out seven more gut-wrenchingly beautiful albums. Her style may not have changed much over the years, but, really, that's the appeal.