This award-winning journalist, who has an Afro-Cuban mom and an Irish dad, grew up in a mostly white suburb on Long Island. Despite this, the anchorwoman says she never struggled with being part of a mixed race family. “I guess I was really good at resisting being put in a box of definitions because my mother was the same way,” O’Brien told Latina Magazine in 2009. She graduated from Harvard and began her journey into media at an NBC affiliate company in Boston. She made her first break as an anchor at MSNBC’s technology program, The Site. From there, she went on to host NBC’s Weekend Today before joining CNN in 2003.