Smaug and Gollum are two creatures that seem to be independent, but very lonely. Although Gollum only has one treasure, and Smaug has many, they both treat those treasures in the same way, they guard them all the time and if something is lost, they will stop at nothing to get it back. Both are similar in many different ways, possessing qualities that cause them to be disliked or pitied. Two of those qualities are curiosity and greed.
When Gollum first encountered Bilbo, his first thought was “I guess it’s a choice feast” (Tolkien 81). He was ready to eat Bilbo, but not after he found out who Bilbo is. Gollum also wanted to find out what he was carrying in his hands. The only thing that Gollum could think of before deciding if he wanted to eat Bilbo or not, was ask him riddles. Gollum believed that Bilbo would get the riddles wrong, and then he would have made his decision, but Bilbo answered each riddle right, making Gollum angrier and angrier. Gollum loves his ring so much that he will do anything to get it back when he realizes that he lost it. He only has his mind set on getting back his ring. In the end Bilbo realizes that Gollum wants to kill him for this reason, and that Gollum became more irrational and dangerous, trying to kill him.
Bilbo’s encounter with Smaug is almost exactly the same as his visit with Gollum. Smaug knew that someone was trying to take his treasure. When he senses that Bilbo is near, he asks him questions. Bilbo was smart with Smaug, and “was not quite so unlearned in dragon-lore (241 Tolkien). Smaug is trying to figure out who Bilbo is, and just as Gollum used riddles to buy time, and figure out what Bilbo was doing, Smaug used clever questions to find out more about Bilbo, and assumed that Bilbo was in his cave only to steal his treasure, ready to spring on him once he told the truth. Just as Gollum thought that all Bilbo wanted was his ring. In the end, Smaug became angry because he could not figure out who Bilbo is.
Both Smaug and Gollum live in lonely places, only thinking about their treasures and guarding them with their life. If they were to encounter anyone who seemed suspicious, they would only believe that person was after one thing. With Bilbo, they were curious and tried to get as much information out of him and the truth, before killing him. They cannot control themselves once they learn that their ring, or treasures are missing, and their greed takes over and causes them to only want to hurt and kill.