There have been six contestants to play Survivor four times. Let’s rank them from worst to first!
Most people are fortunate if they get the opportunity to play Survivor one time, but there have been six total castaways who have gotten a crack at the million bucks a whopping FOUR times!
We already ranked every three-time Survivor player and there have been 23 of those, so the fact that the number whittles down significantly from the third appearance to fourth appearance shows that someone has to be pretty special to return to play the game for a fourth time.
Out of these six players, half of them have won the game at least once and the other three have made the jury in at least three of their four appearances. Pretty impressive.
So, let’s kick the rankings off with a fan favorite!
Ranking Four-Time Survivor Players: Number 6 – Rupert Boneham
Since his initial season back in 2003 with Pearl Islands, Rupert Boneham has been one of the most popular players to ever appear on Survivor. He fit the pirate theme in Pearl Islands to a tee and the first moment we saw him shine was when he pirated the opposing tribe’s shoes while both teams were trying to bargain for supplies.
Rupert took up a vast majority of the air time in Pearl Islands and was so popular that he was immediately brought back for the very next season, Survivor: All-Stars, where he was also a huge star. He was so popular that production invented the America’s Tribal Council special just so they could give Rupert a million dollars.
It’d be another six years before fans would see Rupert again and that appearance came as a member of the Heroes tribe on Heroes vs Villains. His fourth and final appearance came in 2013 when he and his wife Laura appeared on Blood vs Water together.
Now that we’ve gone through Rupert’s timeline, let’s discuss why he’s ranked in the final spot on this list.
For one, he’s never made it to the end despite having the majority alliance twice. He was blindsided in Pearl Islands and ended up finishing seventh that season. In All-Stars, he wisely aligned with Boston Rob and Amber, which took him to the final four, but Rupert never tried to take Rob out and that was his undoing.
In Heroes vs Villains, Rupert was called out by Jeff Probst for blindly sticking with his alliance when it wasn’t necessarily what was best for the tribe. He also advocated to get Stephenie voted second and that put Survivor fans in a conflicting spot, as both were two of the most popular players ever.
Rupert never officially got to play in Blood vs Water, as his wife was immediately voted out of the loved ones’ tribe and Rupert valiantly stepped in to take her place on Redemption Island so his wife could get a chance to play the game. Rupert lost the first duel and as a result, was the first one out of the game.
Rupert might be one of the most popular players in Survivor history, but he’s never been great strategically. If he and Jenna had been ahead of the curve in All-Stars and voted Rob out before it was too late, Rupert could have gone on to win that season, but he never made the move.
Something that rubbed me the wrong way about Rupert was that he was actually kind of a bully at times throughout his seasons. In Pearl Islands, he grabbed Jonny FairPlay by the collar and yelled at him after he cast a vote for him at tribal council.
He also made one of the worst shelters ever in All-Stars and wouldn’t listen to anyone’s opinions regarding the matter. There’s an entire segment in Heroes vs Villains where he’s keeping the entire tribe awake at night because he’s chopping firewood and making tons of noise.
But hey, I get it. Rupert was one of the first beloved members of the Survivor family, which has led to him getting asked to play four total times and got him onto The Amazing Race as well. After his short stint on Blood vs Water, it’s doubtful Rupert returns again.
So much for his dreams.