- Was one of two castaways from "Survivor: Pearl Islands" asked to return and be a castaway on "Survivor: All Stars." After the other castaway (Jon Dalton) declined, he is the only member of "Survivor: Pearl Islands" to be on "Survivor: All Stars".
- With his appearance on "Survivor: Blood vs. Water", he has now competed in four seasons of Survivor, tying a record set by Rob Mariano.
- He loves animals. Rupert has adopted an alligator called Wally, a snake, several fish and frogs and a dachshund called Dixie. He kept a pet snake called Balboa on Survivor (2000), Pearl Islands.
- Politically, Rupert identifies as a Libertarian.
- Frequently works as a motivational speaker and makes appearances for various charities, particularly those dedicated to Anti-Bullying, Dyslexia and Children.
- Since 1991, Rupert has headed a charity dedicated to teaching vocational skills to at-risk teens and young adults.
- Daughter, Raya, born May 13, 1999.
- Was a Professional Wrestler.
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