He began directing music videos at the age of 20 and directed some of the most iconic music videos of all time, for artists such as Dr. Dre, TLC, Mary J. Blige, Outkast and Jay-Z. A Grammy nominee for directing Stevie Wonder and Babyface's How Come, How Long,??? Gray swept the 1995 MTV Music Video Awards, receiving four awards for TLC's Waterfalls??? including Video of the Year, as well as Best