Bragg was born in St. Louis Missouri in 1931. His parents were Vaudeville performers, and 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 eventually settled in California where he began his artistic career. He started by painting portraits of wealthy families, as well as offering lessons. He began to pursue his own creative work and experienced some success. His success came from the humor and satirical style of his work, which often portrayed flaws in American society. His political opinions are featured in his work.
Bragg's works have been showcased in museums and exhibits around the world, and he has had work commissioned by Playboy Magazine.
Bragg lived in Beverly Hills. He had two children and died on January 9, 2017 at the age of 85.