He can boast a best-song Oscar, 10 Grammys, and at least 6 million albums sold. But Legend, 37, also embraces the grunt work of philanthropy—serving on boards, penning editorials, conducting listening tours in prisons and schools—and his advocacy is attracting as much attention as his hits. Last fall the Show Me Campaign, an education-oriented nonprofit Legend founded, launched #FREEAMERICA, a drive to reduce mass incarceration. In a Time op-ed, Legend called on legislatures to “ban the box” requiring job applicants to state whether they have a criminal record—a hurdle that makes it hard for rehabilitated felons to reenter society. The movement took on momentum in November when President Obama banned the box in federal hiring, and it’s one reason the NAACP just gave Legend its President’s Award, a service honor typically given to people decades older.