4. Rupert Boneham
Back-to-Back Seasons: Pearl Islands and All-Stars
The first ever INSANELY popular Survivor player was none other than Rupert of Survivor: Pearl Islands where he was a fan favorite immediately. Rupert fit the pirate theme by his appearance alone, but him stealing the Morgan tribe’s belongings during the pillaging on Day 1 made him an instant star.
Rupert received a lot of air time in Pearl Islands and fans were devastated when he was blindsided on Day 27. He was a lock to return for the first ever All-Stars season, which ended up taking place the very next season after Pearl Islands, making it a short turnaround for Rupert.
Despite coming home and then heading right back out to Panama for another season, Rupert did well in his second season. He went from an eighth place finish in Pearl Islands to making the Final Four in All-Stars. He aligned with Boston Rob after he was absorbed by the Chapera tribe and rode that alliance all the way to the end.
While Rupert has proved over time that he’s not a great strategical player, he’s an old school guy, and that means he was fiercely loyal to his alliances. He proved that in All-Stars and it’s why he didn’t make it to the end. His fourth place finish in All-Stars is still the deepest run he’s had in four tries.
Rupert isn’t someone I typically would want to rank this high, but when you look at his first game and his second game, he did make a huge leap, so he’s fourth here.