He won one million dollars on Survivor: America's Tribal Council which was a special episode of Survivor: All-Stars. The prize was awarded after a popular vote in which Boneham received 85% of the votes cast for the Survivors.

During the game of Survivor: Pearl Islands, Rupert quickly became one of the most popular Survivor contestants, and was well-known for his huge beard, tie-dye shirt and size. Physically fit, personable, and genuine, Rupert was well-liked by many of his competitors and managed to win many team and individual challenges. His plan was to win the game by being the most capable at winning challenges, providing for his camp, and being sincere. He preferred to rely on 'fair play', although he was responsible for stealing the opposing tribe's personal supplies in the first episode. Boneham's genuine but flawed strategy earned him eighth place in Pearl Islands. Rupert remained more low-key during the "All-Star" season where he placed fourth. A sensitive man, Rupert felt offended by contestants who played "dishonestly" through lying and deception.

Conversely, Rupert's detractors found him to be a bully and an intimidator when he angrily, and nearly physically, confronted one of his fellow tribemates to demand to know why he would attempt to vote him out of the competition. Many of those same detractors believe that Survivor: America's Tribal Council was orchestrated by CBS for the sole purpose of giving him a million dollars following the overwhelming response from viewers when he was eliminated from Survivor: Pearl Islands.

Born in Detroit, Michigan, he moved to Indiana at a young age. He attended Haworth High School in Kokomo, Indiana. After graduation, he moved to Texas to study nursing at Cisco Junior College and Angelo State University.

Boneham lives in Indianapolis, Indiana with his wife Laura and daughter, Raya. Prior to appearing in Survivor, he worked as a mentor for troubled teens. He has previously worked as a gravedigger and bartender. His hobbies include scuba diving, camping and coin collecting. His favorite sport is racquetball.

Boneham used his winnings to buy a home, set up a college fund for his daughter, pay off his and his mother's debts and start Rupert's Kids, a non-profit organization dedicated to helping troubled teens, especially those mired in the juvenile court system. Since All-Stars ended he has appeared in promotions for local Indiana businesses as well as national promos for Survivor: Vanuatu. In 2006, Rupert appeared in the independent movie, "Open Mic'rs".