Sheldon Bailey was born in Germany on a US Army base and spent his formative years bouncing from San Antonio to Fort Knox before finally landing in Fayetteville, NC. Finding his niche in theater in the eighth grade, Bailey balanced his creative and athletic aspirations throughout high school. During his senior year, the multifaceted 6′6″ thespian attended a prestigious basketball boarding school. Transitioning to college as a student at Winthrop University, he transferred to Florida International University after his sophomore year where he served as the Black Student Union President.
After college, he played professional basketball in China, Taiwan, Ecuador, and domestically in the CBA and ABA Leagues. Bailey's work with the ABA landed him in Los Angeles where he subsequently auditioned for the film Semi-Pro. By 2013 Bailey had established an impressive list of acting credits in short films and commercials.