This is a tough one.
Smaug is one of my favorite characters. His chatter with Bilbo is priceless.
But Glaurung did more damage I believe (played a roll in a couple big battles and overthrew Nargothrond). And he was also killed in a cooler way, by a much greater slayer.
And the weapons used- you have a lucky arrow versus the sword destined to slay Morgoth himself.
*squirms*
++Glaurung
But really I'd be happy with either one winning.
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