There are few entertainers who are able to maintain a career, a successful marriage and family, and a very public personality for a decade, let alone four. William “Bill” Cosby is just one of those people. Over the course of his career (with its early beginnings as a comedian, through television, movies, records, producing, directing, and writing) Cosby has had spectacular successes (“I Spy” and “The Cosby Show”) and some equally amazing failures (“Ghost Dad” and “Leonard Part 6”). His comedy albums sold millions of copies, “Fat Albert” was one of the most widely watched cartoons of the 1970’s, and his contribution to Children’s Television has gone unmatched. Cosby has had struggles of a personal nature too, most notably the drive-by killing of his son, Ennis. Over the course of this paper, Bill Cosby’s career and life will be discussed chronologically, and will focus on his achievements on a personal, professional, and familial level.