We're nearing the end, second hints for the top 5. A little piece of bonus info: It's probably hard to see, but whenever I've used _ in my hints I make sure the number of them fits the missing word/name.
5) A stealthy character that you don't play as in any of the three main campaigns offers major guidance in all three
Hint 2: He is essentially to Amon what Gandalf is to Sauron.
4) The protagonist of this game would hate #3 (Portal 2)
Hint 2: He has made a crossover appearance in another big game series, the name of which is very fitting for his profession
2) Contains countless references to other media, particularly Lord of the Rings and Monty Python and the Holy Grail.
Hint 2: And references to two other big series by the same developer, including a certain Leg.
1) "Don't overdo it"
Hint 2: "_____, ...don't die (before I do)."
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