Countless Winfrey was born and raised in Nashville, Tennessee. She began her dance training at Dance with Stacy Dance Studio, where she danced more than five years. She also attended Wharton Arts Magnet School where she majored in dance and art. She later continued her training at Nashville School of the Arts. Attending college at the University of Memphis, Countess graduated magna cum laude with a BS degree in health and human performance and a minor in dance in 2011.
She has also participated in a variety of dance festivals including the American High School Dance Festival, the American College Dance Festival (2009, 2010, 2011 and 2012), the American Dance Festival and the David Dorfman Dance Winter Intensive.
After graduating, Countess joined DCDC2 in 2012, where she danced for two years while having the opportunity to perform with the first company in her second year. She has performed works by Paul Taylor, David Dorfman, Rodney A. Brown, Rob Priore, William B. McClellan, Jr., and many other choreographers.