Although he is clearly a villain, the character of Gollum is one of the most pitiful and sympathetic villains ever to grace the pages of novels. This is especially true from the point of view of Bilbo Baggins, one of the few characters to face off against Gollum directly. When compared to the other villains in The Hobbit, this becomes even more obvious. Bilbo first encounters the trolls. There are only three of them, but the fact that they are “very large persons” gives them a large advantage over all the dwarves and of course the very small Bilbo (39). The goblins, on the other hand, have the advantage by sheer strength in numbers. They “were six to each dwarf,” giving Bilbo and his comrades no chance of escape or victory (67). Meanwhile, Gollum is actually at a disadvantage, it is “not a fair fight” to him, for it is one on one, and Bilbo has a sword and the ring at his disposal, while Gollum’s only weapons are his own hands and feet (96). Then we come to each villain’s immediate reactions to Bilbo and the dwarves. Upon capturing Bilbo, the trolls immediately want to know if you can “cook ‘em” (41). The goblins treat their prisoners cruelly, they “were very rough,” and “took out whips and whipped” Bilbo and the dwarves, and also presented no plans other than to eat their prisoners (67,68). Gollum is quite different. Though it is clear to the reader that he plans to consume Bilbo, that fact is quite unclear to the hobbit himself, as Gollum “was anxious to appear friendly,” and starts off by playing a riddle game, providing Bilbo an opportunity for escape (81). Also, “Gollum had not actually threatened to kill” Bilbo (96).
Then of course comes the executions of the plans of the villains. The trolls make for poor villains, as they have “a gorgeous row” among themselves and waste a lot of time “arguing” how to cook their victims (42, 45). They are clearly stupid, and cause their own doom when easily tricked by Gandalf. The goblins are much more clever than the trolls, but in the end, their downfall is caused by a simple fear of two weapons. Gollum is also rather clever, coming up with riddles and being able to answer Bilbo’s riddles. In fact he is never truly tricked by Bilbo, though he does have some mistaken ideas. Something else leading to Gollum’s haplessness is his clear insanity. He calls himself “my precioussss,” and even has “an argument with himself” (80, 93). Finally, Gollum is just a sad creature who brings Bilbo’s “heart to his mouth” (96). Gollum “was miserable, alone, lost,” which gained him “a sudden understanding, a pity mixed with horror . . . in Bilbo’s heart” (96). In the end it is Gollum’s intense sadness mixed with insanity that garners him much pity in both Bilbo and the readers’ eyes. It is difficult to blame such a pitiful creature for his actions.