Bragg was born in St. Louis Missouri in 1931. Both of his parents were Vaudeville performers, so he spent most of his young life traveling on tour with them. During his teenage years, he went to New York's High School of Music and Art in Harlem. At 18, he ran away with his high school sweetheart, fellow artist, Jennie Tomao.
Before pursuing art, Bragg worked as a cab driver, a truck driver, a stand-up comedian, and a factory worker. He finally settled in California where he began his artistic career. He started by painting portraits of wealthy families, as well as offering lessons. Eventually began to pursue his own creative works. As he started using his own creativity and imagination, he started becoming successful. His works satirized the nature of the society he viewed. His success came from the humor and satirical style of his work. His political beliefs and opinions are very prevalent in his work. He has often referred to himself as "devoted student of the human race" and an "observer." His works have been showcased in museums and exhibits around the world, and has been commissioned by Playboy Magazine. PBS made a documentary about him called "Charles Bragg - One of a Kind." He has published a book on his work, "Charles Bragg: The Works! A Retrospective"