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This is a very interesting question, however things are quite different in the book and in the movie, the short answer is that Smaug probably didn't know about the ring nor Sauron, the long answer is explained below.

In the book Bilbo entered in the mountain 3 times, the first time Smaug is asleep and he steals a golden cup, he then returns to the dwarfs who convince him to enter Erebor again. The second time Smaug is awake and angry for the theft, he talks with Bilbo (who tricks him into showing his weak point) and despite talking about the cup he never said the exact sentence you quoted from the movie. The third time Bilbo enters the mountain toghetertogether with the dwarves.
So I'd say that in the movie Smaug is referring to the ring, even though it isn't explained how he knew about it and this precise scene didn't happen in the book.


The second question is even harder to answer because, even in the extremely detailed universe created by Tolkien, very little is said about dragons (only 4 of them are actually named).
What we know is that dragons were originally bred by Morgoth and that Sauron (who was Morgoth's disciple) used them in the famous war of the rings so some dragons surely knew Sauron and the rings (4 of the rings given to the dwarves were meltmelted by dragons).
We don't know a lot about Smaug, he is the last great dragon on Middle-Earth but there is no way to tell for sure wetherwhether he knew Sauron and the rings.


I'm not sure wetherwhether Smaug says something about the darkness incoming in the book (he doesn't in the dialogue with Bilbo, but I'd need to check wetherwhether he speaks in other parts of the book too), but he can probably just perceive it, since he can feel magic and Sauron is gathering a huge power.
I think this (and maybe Smaug knowing about the ring too) are details added by Jackson to contestualizecontextualize the tale told in "The Hobbit" inside Tolkien's universe and timeline.

I confronted the most important details with online sources, but it has been a long time since I read "The Hobbit" and "The Silmarillion" so I may be missing some (potentially important) details

This is a very interesting question, however things are quite different in the book and in the movie, the short answer is that Smaug probably didn't know about the ring nor Sauron, the long answer is explained below.

In the book Bilbo entered in the mountain 3 times, the first time Smaug is asleep and he steals a golden cup, he then returns to the dwarfs who convince him to enter Erebor again. The second time Smaug is awake and angry for the theft, he talks with Bilbo (who tricks him into showing his weak point) and despite talking about the cup he never said the exact sentence you quoted from the movie. The third time Bilbo enters the mountain togheter with the dwarves.
So I'd say that in the movie Smaug is referring to the ring, even though it isn't explained how he knew about it and this precise scene didn't happen in the book.


The second question is even harder to answer because, even in the extremely detailed universe created by Tolkien, very little is said about dragons (only 4 of them are actually named).
What we know is that dragons were originally bred by Morgoth and that Sauron (who was Morgoth's disciple) used them in the famous war of the rings so some dragons surely knew Sauron and the rings (4 of the rings given to the dwarves were melt by dragons).
We don't know a lot about Smaug, he is the last great dragon on Middle-Earth but there is no way to tell for sure wether he knew Sauron and the rings.


I'm not sure wether Smaug says something about the darkness incoming in the book (he doesn't in the dialogue with Bilbo, but I'd need to check wether he speaks in other parts of the book too), but he can probably just perceive it, since he can feel magic and Sauron is gathering a huge power.
I think this (and maybe Smaug knowing about the ring too) are details added by Jackson to contestualize the tale told in "The Hobbit" inside Tolkien's universe and timeline.

I confronted the most important details with online sources, but it has been a long time since I read "The Hobbit" and "The Silmarillion" so I may be missing some (potentially important) details

This is a very interesting question, however things are quite different in the book and in the movie, the short answer is that Smaug probably didn't know about the ring nor Sauron, the long answer is explained below.

In the book Bilbo entered in the mountain 3 times, the first time Smaug is asleep and he steals a golden cup, he then returns to the dwarfs who convince him to enter Erebor again. The second time Smaug is awake and angry for the theft, he talks with Bilbo (who tricks him into showing his weak point) and despite talking about the cup he never said the exact sentence you quoted from the movie. The third time Bilbo enters the mountain together with the dwarves.
So I'd say that in the movie Smaug is referring to the ring, even though it isn't explained how he knew about it and this precise scene didn't happen in the book.


The second question is even harder to answer because, even in the extremely detailed universe created by Tolkien, very little is said about dragons (only 4 of them are actually named).
What we know is that dragons were originally bred by Morgoth and that Sauron (who was Morgoth's disciple) used them in the famous war of the rings so some dragons surely knew Sauron and the rings (4 of the rings given to the dwarves were melted by dragons).
We don't know a lot about Smaug, he is the last great dragon on Middle-Earth but there is no way to tell for sure whether he knew Sauron and the rings.


I'm not sure whether Smaug says something about the darkness incoming in the book (he doesn't in the dialogue with Bilbo, but I'd need to check whether he speaks in other parts of the book too), but he can probably just perceive it, since he can feel magic and Sauron is gathering a huge power.
I think this (and maybe Smaug knowing about the ring too) are details added by Jackson to contextualize the tale told in "The Hobbit" inside Tolkien's universe and timeline.

I confronted the most important details with online sources, but it has been a long time since I read "The Hobbit" and "The Silmarillion" so I may be missing some (potentially important) details

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This is a very interesting question, however things are quite different in the book and in the movie, the short answer is that Smaug probably didn't know about the ring nor Sauron, the long answer is explained below.

In the book Bilbo entered in the mountain 3 times, the first time Smaug is asleep and he steals a golden cup, he then returns to the dwarfs who convince him to enter Erebor again. The second time Smaug is awake and angry for the theft, he talks with Bilbo (who tricks him into showing his weak point) and despite talking about the cup he never said the exact sentence you quoted from the movie. The third time Bilbo enters the mountain togheter with the dwarves.
So I'd say that in the movie Smaug is referring to the ring, even though it isn't explained how he knew about it and this precise scene didn't happen in the book.


The second question is even harder to answer because, even in the extremely detailed universe created by Tolkien, very little is said about dragons (only 4 of them are actually named).
What we know is that dragons were originally bred by Morgoth and that Sauron (who was Morgoth's disciple) used them in the famous war of the rings so some dragons surely knew Sauron and the rings (4 of the rings given to the dwarves were melt by dragons).
We don't know a lot about Smaug, he is the last great dragon on Middle-Earth but there is no way to tell for sure wether he knew Sauron and the rings.


I'm not sure wether Smaug says something about the darkness incoming in the book (he doesn't in the dialogue with Bilbo, but I'd need to check wether he speaks in other parts of the book too), but he can probably just perceive it, since he can feel magic and Sauron is gathering a huge power.
I think this (and maybe Smaug knowing about the ring too) are details added by Jackson to contestualize the tale told in "The Hobbit" inside Tolkien's universe and timeline.

I confronted the most important details with online sources, but it has been a long time since I read "The Hobbit" and "The Silmarillion" so I may be missing some (potentially important) details