Years active: 1995-Present
Accolades: 31x Grand Slam champion, 3x WTA Tour Championships winner (2001, 2009, 2012), 4x Olympic gold medalist (2000, 2008, 2012), WTA Player of the Year (2002, 2008, 2009, 2012), highest grossing female player ever (over $40 million in prize money)
Serena Williams burst onto the pro scene at age 14 in 1995, but she was very much in the shadow of her older sister Venus. By 1999, however, she had won her first Grand Slam title at the U.S. Open, and made it onto this memorable Sports Illustrated cover. That photo of her—the snarling features, pure power, crazed eyes—is an iconic snapshot of her career, and foreshadowed a future career of badassery. Being a champion is dope in itself, but the way Serena has done it has made her a symbol of female empowerment and black strength. Whether it's hurling threats at a line judge for not getting a call, or bodying the women's game like nobody else has, Serena is totally unfuckwittable in the realm of badass American tennis players, men and women alike.