Born and raised in Boston, Massachusetts, comedian Robert Kelly earned regular spots on the Opie & Anthony radio program while also establishing himself as a veteran of Dane Cook's Tourgasm. As a teenager, episodes of petty theft and vandalism sent him to juvenile prison for two years. After his release, Kelly developed a completely renewed perspective on what lay ahead. Focused work during high school secured him a scholarship to community college, where he concentrated on fine arts. Although creativity brought satisfaction and his paintings drew favorable responses, the activity lacked the intensity he craved. An improv comedy troupe supplied that missing charge and introduced him to Dane Cook, initiating a friendship that persisted once the pair pursued separate standup paths. Following several years on the comedy club and college campus circuit, Cook—by then a comedy superstar—invited Kelly to join the Tourgasm troupe for a cross-country tour that became an HBO television series in 2006. Two years afterward, Kelly issued his debut album, Just the Tip, on the Comedy Central label.
