Bobby was born at Milingimbii Island and attended school at the mission. He later worked as a stockman at Nangalala station and later at Murwangi Cattle Station.

Bobby was a songman for his community and toured both nationally and internationally with David Gulpilil and later with his band, Wak Wak Jungi. He has also appeared in films including Across the Top and Ten Canoes, both educating the world about traditional Arnhem Land life.

Bobby is a sought after artist and has had a long and successful art career. His works have been displayed in numerous exhibitions and his works are found in many private and public collections.