I think this discussion so far has forgotten about one of the most obviously humble characters of all: Sam Gamgee.
All of the hobbits are self-effacing, to be sure; but Sam really takes the cake when it comes to putting others (especially his Master) above himself, to the point that one wonders a). if he has serious self-confidence issues, possibly brought on by the Gaffer's sharp tongue, or b). if he actually has some appreciation of his own talents but never expresses it because it's not his place.
Then there's his attachment to Frodo, of which pride plays a huge part:
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Originally Posted by Letters 246
Sam was cocksure, and deep down a little conceited; but his conceit had been transformed by his devotion to Frodo. He did not think of himself as heroic or even brave, or in any way admirable--except in his service and loyalty to his master. That had an ingredient (probably inevitable) of pride and possessiveness: it is difficult to exclude it from the devotion of those who perform such service. In any case it prevented him from fully understanding the master that he loved, and from following him in his gradual education to the nobility of service to the unlovable and of perception of damaged good in the corrupt. He plainly did not fully understand Frodo's motives or his distress in the incident of the Forbidden Pool. if he had understood better what was going on between Frodo and Gollum, things might have turned out differently in the end. For me perhaps the most tragic moment in the Tale comes in II 323 ff. when Sam fails to note the complete change in Gollum's tone and aspect. 'Nothing, nothing,' said Gollum softly. 'Nice master!' His repentance is blighted and all Frodo's pity is (in a sense) wasted. Shelob's lair became inevitable.
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Sorry for the long quote, but I'm a huge fan of context. I'd say that this is the closest anyone in LotR comes to having pride in one's humility--Sam is proud of his devotion
as Frodo's manservant, which necessarily means putting himself in a lowered position.
There's one other incident with Sam's pride vs. humility that I can think of off the top of my head, and here the interesting thing is that we've got his duty and station warring with impressing the girl:
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Originally Posted by The Scouring of the Shire
'Well, you can't say fairer than that,' said the gaffer. 'Mr. Frodo Baggins is a real gentlehobbit, I always have said, whatever you may think of some others of the name, begging your pardon. And I hope my Sam's behaved hisself and given satisfaction?'
'Perfect satisfaction, Mr. Gamgee,' said Frodo. 'Indeed, if you will believe it, he's now one of the most famous people in all the lands, and they are making songs about his deeds from here to the Sea and beyond the Great River.' Sam blushed, but he looked gratefully at Frodo', for Rosie's eyes were shining and she was smiling at him.
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Finally, we have his later history to look at. Sam becomes ennobled in Shire society, through Frodo's inheritance and his being elected a whopping number of times to the mayoralty, which would have to imply that he does know deep down by now that he has the skill to use money, power, and influence effectively. But I still can't see him without some of his "oh, it was nothing" demeanor, both because that's how hobbits are and that's how Sam is. And that's
really effective stuff politically, especially if it gets around how you're actually friends with the King, etc.
So going back to my a vs. b above, I don't think that Sam ever had issues with self-confidence. There may have been things he thought he couldn't do, but that was due to restrictions of class. He was a fine gardener and a fine cook and he knew it, and he tried to serve his Master in the best way possible. But all of those things, he thinks (at least in LotR), aren't what it takes to save the world. Sam must have learned that it did somewhere along the way, or else he never would have stood for going beyond his station. He just never let that on.
I think this had a point relevant to the thread somewhere, but if it did, I lost it.