After a wait of a couple of years, I have finally updated these rankings. I tend to rank gameplay seasons higher than "entertaining" seasons, but that's not a hard and fast rule. Mostly, it's just my opinion of how entertaining the seasons are. I haven't really watched any back (despite my many promises that I will) so some are going off of memory, which could skew the rankings.
Without further ado, here are my rankings, first summarized, then a bit more detailed.
Survivor: Heroes vs. Villains
Survivor: Micronesia - Fans vs. Favorites
Survivor: Blood vs. Water
0. Survivor: Borneo (Season 1)
It is difficult to rank the first season when compared to the others. It is the season that laid the blueprint for how every other season was played, and yet the one that also helped to define how we, the viewers, were to watch the show. So I cheated, and took it out of the rankings.
1. Survivor: Heroes vs. Villains (Season 20)
In this case, familiarity helps. Knowing each of the players going in and how they were likely to play set some expectations. The season lived up to it and more. The casting of players and characters was fantastic. The winner was a bit disappointing, but the lead to the final tribal was great.
2. Survivor: Micronesia - Fans vs. Favorites (Season 16)
A lot of blind sides, the single stupidest move in Survivor history and some interesting characters introdued. Awesome season.
3. Survivor: Peal Islands (Season 7)
Rupert is overexposed now, but in Season 7 he was an amazing character, one whose embracing of the Pirates theme of Pearl Islands gave the season a great start, and then gave us someone to root for throughout the season. Plus, you get Johnny Fairplay and the greatest lie ever told in Survivor (until poor Ice Cream Scooper Erik and the giving away of immunity.) And we have possibly the greatest player ever to play the game (especially if you go by results) in Sandra playing her first season.
4. Survivor: Cagayan (Season 28)
Rupert. Johnny Fairplay. The season that Survivor became fun to watch for reasons beyond the actual game.
5. Survivor: Samoa (Season 19)
Putting aside the jury vote, this season was a win simply because of Russell. His play reinvigorated the show and the game.
6. Survivor: Amazon (Season 6)
The first season where alliances were fluid. The game was played in a much different manner than before, with votes moving continually.
Oh, and chocolate and peanut butter.
7. Survivor: Blood vs. Water (Season 27)
A lot of people groaned when they heard the details about this season. Half returning players, half family members? The return of Redemption Island? "UGH," they said. As it turned out, both twists helped to carry the season through what would have been (frankly) a boring end game. Instead of just getting (essentially) a Pagonging of the minority, we also saw an emotional challenge between mother and daughter where the loser gets eliminated, a DRAWING OF ROCKS where the clear cut favourite could have been eliminated and some of the most aggressive Tribal Council play from somebody who knew his time in the game was on the line from Hayden. And that's not even the half of the season.
8. Survivor: Worlds Apart (Season 30)
The only person who could win and make it an acceptable season did win. But the season itself was great for gameplay, and not so great for misongyny and general not niceness from people who truly believe they are in the right. Unfortunately, the latter definitely overshadows the former, which ends up hurting the season.
9. Survivor: Caramoan (Season 26)
The focus on the big characters in the first half of the season was a bit ominous for those who prefer the strategy of the season, even if it was interesting to watch (enjoyable doesn't reflect how uncomfortable it could be to watch Brandon break down and Shamar be Shamar.) But once the merge hit, the blind sides came non-stop, we had a shocking tribal council with two idols in play which caused us to see the first ever scramble during tribal council, someone getting blindsided with an immunity idol in their pocket, one of the greatest speech ever getting voted out, a generally likeable cast from final 9 onward and yes, even a satisfying winner. Pretty well everything that you could want in a season, you got.
(Though the bullying of Dawn was awkward at best.)
10. Survivor: Phillipines (Season 25)
This season had a couple of epic tribal councils and the most inept tribe ever, and a complete flip of the game when that inept tribe ended up in the final four. Plus Penner's final jury questions/speech. Combine that with the existance of Abi-Maria and you have a very great season.
11. Survivor: Palau (Season 10)
The first season where we saw a true dominant tribe. Then came Stephanie's survival for 2 weeks, then Tom's bold move to threaten to tie a vote to get people on side with him (looking back at it, it doesn't seem to be as bold but at the time it was an amazingly ballsy play). Very underrated year.
12. Survivor: China (Season 15)
Looking back on this season with the knowledge of how Todd has fallen apart since it aired, it does make ranking this season within the context of just the season more difficult. But looking at it from just the season itself, it has James' stupid non-play of a hidden immunity idol, Todd wearing his bad deeds, and Amanda's first final tribal council failure. A pretty good year.
13. Survivor: Australian Outback (Season 2)
The beginning of the Jeff Probst/Colby Donaldson bromance. Also the first ever major strategic blunder, though it was at least done out of some sense of loyalty. Plus Mike Skupin's epic injury, a bad tie-breaker being used to take out Jeff Varner and the launch of Elizabeth Hasselback's career.
14. Survivor: Cook Islands (Season 13)
Two of the most likable players in Yul and Ozzie. It also had the funniest Survivor moment, when Sundra and Becky "battled" to build fire. Taking 90 minutes to do so. After being given matches 30 minutes in.
15. Survivor: Tocantins (Season 18)
J.T. and Stephen dominate the year; we're also given the gift of the Dragon-Slayer, Coach!
16. Survivor: Africa (Season 3)
Oh, Brandon. You are still not forgiven for screwing over Kelly for no good reason. But with that said it is a fun season where we have our first tribe swap, and our first tease of a switch of the majority alliance.
17. Survivor: Redemption Island (Season 22)
The Boston Rob show gets up here because of Boston Rob's hilarious confessionals, his running of the show from start to finish and Phillip's wackiness. In an unrelated note, if Rob didn't win I would have rated it lower.
18. Survivor: One World (Season 24)
The removal of Colton stopped us from seeing him get his comeuppance that we so richly needed. But at the same time, we had great characters in Tarzan and Kat, an amazing situation where a tribe won immunity then decided to give it away so that they could vote somebody out and possibly the greatest game ever played on Survivor by Kim. It's tough to keep it this low, but predictability beats the game itself.
19. Survivor: Panama (Season 12)
The Terry year, where his loss of the final immunity challenge (under questionable means) ended up giving us Aras as a winner. Awesome for Terry's dominance, not so awesome for everything else.
20. Survivor: San Juan del Sur (Season 29)
The second coming of the Blood vs. Water was nowhere near as strong as the first
21. Survivor: Fiji (Season 14)
I rank this higher than everybody else it seems, but Yau Man and Earl were fun to watch, and the drama of Dreamz not giving immunity to Yau Man at the final 4 (after being gifted a car by Yau Man in exchange for a promise of the necklace) made it enjoyable (even if the have/have not twist was possibly the second worst twist of all time.)
22. Survivor: Guatemala (Season 11)
Stephanie gets a second chance and turns into a mean person. And then she loses to Danni. But it did have Gary Hogeboom thinking he needed to disguise who he was from everybody else, lest they remember a backup quarterback from the NFL. And also, the first season with what is now a big part of Survivor, a hidden immunity idol.
23. Survivor: Vanuatu (Season 9)
Probably the most difficult to place. Chris's victory when outnumbered 5-1 and with not winning immunity was impressive, but the show was horrible before that.
24. Survivor: South Pacific (Season 23)
The editing ended up hurting this season, as they built it up to show why Coach lost, instead of why Sophie won. Maybe that happened because they had very little to use to show Sophie as a great player, but that's an even bigger damning of the season.
(Also, the first half of the year with Brandon acting very creepy towards Mikayla was uncomfortable at the best of times.)
25. Survivor: All-Stars (Season 8)
It gave us Boston Rob and Amber as a power couple, but it also gave us the biggest farce of a final council before Samoa. And the overriding theme of the previous winners didn't deserve to stay around becaue they had already won was annoying and uncomfortable.
26. Survivor: Marquesas (Season 4)
This should rank higher. It gave us Boston Rob, whatshername being carried to the island like Cleopatra, and the first shakeup of the status quo. But it was the most frustrating final two ever, with both not really deserving of being there.
27. Survivor: Gabon (Season 17)
You remember how great it was that Bob Crowley won, but when you think about it more, the season was pretty terrible. Bob Crowley was just a likable person, not a good player. When the most memorable things to have happened was an amusing fake hidden immunity idol and Bob making his buff into a bow tie, you know you have a terrible season.
(Though thankfully it did give us Corrine.)
28. Survivor: Nicaragua (Season 21)
It was a tedious season until Fabio went on his immunity streak. By breaking up the boot order, Fabio rode to victory, and gave us a likeable winner, which puts this ahead of...
29. Survivor: Thailand (Season 5)
Easily the most unlikable cast in Survivor history overshadows one of the greatest games played by Brian Heidik. The final immunity challenge was cool, but otherwise it was a horrible season to watch. No tribal swap, no merge until the jury and we were left with waiting for the Pagong-ing to finish. And one of the best games played was rewarded with a 4-3 victory versus a terrible person.