Other characters: None in-game at the moment.
Character name: Samwise Gamgee
Series: Lord of the Rings
Canon point: During Two Towers; specifically, the crossing of the Dead Marshes.
Not a wiki link, but this is meatier then a lot of the wikis I found.
Sam has been described in many ways during his travels. Frodo, in light of all that he'd learned of Samwise and his hidden talents, remarked that he had been a conspirator and a jester, and says that he could end up becoming a knight or a wizard by the end of their journey. His father, Gaffer Gamgee, frequently scolds Sam for his preoccupation with fantasy and old tales, and fears that the distraction may land him in considerable trouble. Aragorn refers to him as "stout-hearted" when Sam and Frodo's cousins confront him loudly and prepared for combat after taking Frodo from the Inn's common-room. Pippin, while vouching for Sam's character to his elder cousin, says: "Sam is an excellent fellow, and would jump down a dragon's throat to save you, if he did not trip over his own feet." Full of surprises, ferociously loyal and unendingly hopeful, Sam makes for a powerful friend to have, despite his diminutive size.
Sam possesses a deep loyalty for his friends - the Bagginses of Bag End in particular, and his attachment and will to protect Frodo from harm are shown many times. Sam volunteers his rations and water to his master when the Ring's weight grows, offers him encouraging words, and tends to the ills that the Ring causes. While he can never tell the true horror of bearing the Ring as an outside observer, he knows that it is leeching poison into Frodo, and he does all that he can to alleviate the pain of it: he cooks, sings, and guards him with his life, often considering Frodo's well-being far before his own. Sam is also the only one of Frodo's original nine companions to make good on his vow to accompany him into the Black Land itself, and is very willing to fight for his master's ensured safety. He time and time again stands firmly against anything and anyone that he deems a threat - including full-grown Men, the Ringwraiths, and other characters of larger size and importance then a Hobbit of the Shire. To some, it may seem that his dauntless nature causes him to forget his size; as a hobbit of humble Harfoot lineage, Sam only hovers around 3'4", and stands as the third-shortest of the hobbits of the Fellowship only because Peregrin Took is, by Halfling years, a child. Still, when it comes to defending his master, he rarely takes his size into account, and he likely really would jump down a dragon's throat if it meant retrieving him.
As Samwise is not a cowardly Hobbit, he is also among the more straightforward of his kind. He tends to speak very frankly, and if he distrusts or dislikes someone, he never makes a secret of it. He is frequently openly hostile toward individuals that he feels are untrustworthy when he should likely simply be cautiously courteous, and this social carelessness has only grown stronger since joining the Fellowship. While the particulars of the Ring remain a mystery to Sam, the enormity of it is clear to him. He understands the care that they must take, the evil and betrayal that it inspires in the hearts of even their own, trusted companions, and he is especially quick to question the motives of strangers. This can likely make him seem very rude and paranoid to the outside eye, especially when one contrasts Sam's often prickly nature with Frodo's calmer and more civil demeanor. This paranoia often illicits a poor response from others, and can forcibly alienate him from possible friends. Sam tends to also pick fights or worsen situations when it could be avoided with tact, and lends him to picking fights with those far larger and stronger then he is. Additionally, while his intentions are often noble, this can often lead him into taking up less-then-savory methods to assure a task that he deems important is done. While he knew that spying on Frodo was wrong, the insistence that his master was in some kind of trouble was all that was needed to goad him into acting further. He can easily condone less desirable actions if he deems the end result important enough, and especially when that end result is concerning something especially important to him.
Being less susceptible to trust hardly makes him invulnerable to his share of naivete, however. He is largely driven by the intangible; gut feeling and sentiment, as opposed to rationalism and logic. His only reasons for accompanying Frodo are emotional - he doesn't join the Fellowship for gain or glory, and instead joins insisting that he must be at his side to ensure his safety, despite four very skilled warriors and one wizard already accompanying him, all of whom could logically outperform him in combat and the defense of Frodo. Similarly, his reasons for doubting Gollum can be chalked up to a simple bad feeling, to a point. It's simply a matter of tripping the wrong (or right) intangible criteria; Sam will either take to you, or he will not. Though his trust can be built for those who do not, it can be a long process. The quickest way to gain Sam's trust is to go through Frodo (if he will let you close enough, that is) but the next best thing is simply putting effort forward into appearing trustworthy. He will often carefully watch those who have landed in his distrust, and internally track justification for his wariness, and if you give him none, his distrust is likely to die down.
His simple outlook also allows him something else exceedingly important to the quest at hand: his unending optimism. For Sam, there is only one outcome he will entertain for the quest of the Ring, and that is victory through perseverance and a safe return to home and normalcy. He is so hopeful of their victory, so blinded to anything else, that he does not imagine any other outcome for a very long time. He doesn't consider that the quest might leave any sort of damage that he can't quantify or understand, or that there is any capacity for failure as long as he keeps going. Even as he slowly begins to realize that they might not emerge from all that the quest is unscathed - or, perhaps, even alive - Sam does not lose faith. He continues on, as he feels he must, despite realizing that their fate is not as in hand as Sam might have thought.
Powers: Sam, as far as Hobbits go, is a mundane specimen in this department - he is rather skilled in many skills considered necessary to run a Hobbit household, knowledgeable in the ways of herbs and roots, and he has some natural proficiency in walking and sneaking. His large, fur-covered feet have leather-thick soles, and this allows him to walk for long stretches of time.
Entry: Sam will arrive in Jawson's Bog, but he's not likely to seek out the Bastion before finding Frodo, so he might need some steering to make it there.
Other: Sam has taken some articles from Middle-Earth in his large pack; his sword, the ash-grey box and the Elven rope from Galadriel, a trowel, a small supply of Lembas that he will save for unfortunate chance, his pipe, a little wooden box of fine Shire salt and seasonings, a small pouch of dried pipeweed, a single roll of bandages, and a heavy cast-iron skillet. The items that did not make it to the Bastion with him include flint and tinder, pots and pans of varying sizes, his bedroll, a mending kit, dried rations and herbs, and most of his medical supplies.