Sheryl Crow

2009

SHERYL CROW, 47

As a singer-songwriter looking for her big break in the music business, the Grammy winner found herself at a crossroads. Struggling "between being a vamp and being credible as an artist," the single mother to son Wyatt (who turns 2 on April 29) has learned that it doesn't have to be one or the other. At a Grammy SoundCheck event last year, Crow said, "I can look pretty and wear makeup and not be afraid it will take away my credibility."