Originally posted by Darkstorm ZeroStop using book terminology man.
I'll say this, without the light of Erandil, Sam would have been Shelob's next egg incubator while she drained Frodo dry.However, he did stand up to the Uruk's at the battle of Amon Hen, and later wrecked what was left of the Cirith Ungol garrison solo to rescue Frodo.
I have not had a chance to see Hobbit 2 yet though, so my knowledge of the events is almost purely from the books, but his stand against Azin in the first Hobbit movie speaks volumes as to Bilbo's courage being comparable at least to that of Sam. Courage and skill are 2 very different things here though, so if he didn't take on Smaug head on, then he isn't going to win over a skill contest against someone who managed a significant win over Shelob.
Now, don't get me wrong either. Dragons are frigging badass opponents, easily on par with any demons that Udun ever produced, but the Dragons of the 3rd age are actually much less when compared to 1st age ones like Ancaladon and other 1st age demons. then again, Shelob is also considerably less than Ungoliant... One that managed to screw over Morgoth, who had to call out to 1st age balrogs to rescue him.