I'm withdrawing this entry; I can't be bothered with the finishing touches, especially as they're half done already but left 200km away! ::) Not really worth an award anyway; I was angling for impact and flavour text more than humour or inspiredness, but I think I hit those latter two with my other entry, which on the whole works much better.

Despair is a strange thing. It can tear people, families, communities apart; but it also grows when there's nothing left to divide, and then, sometimes, it can bring people together. These five wanderers have lost much, all but their very lives -- yet they live on, mere sparks of vitality. They are the Grey Men, for even if they have lost the will to shine through their despair, yet maybe together these five sparks can light their own way.
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Using The Grey Men: The Grey Men are suitable NPCs in any setting which has seen large-scale devastation and loss of life in recent years: war, plague, natural disaster, famine, etc. They make suitable allies, or at least benign acquaintances, for most parties (particularly good-aligned ones), but could also come into conflict with the PCs for any number of reasons (outsider adventurers are unwelcome in the region nowadays; the PCs are working for someone unpopular; the two parties fight over a deer or a couple of sheep; etc.) The Grey Men are wanderers for the most part, but if there is some quest that could ease the prevailing misery, they make suitable ready-made PCs, or they may find themselves competing with -- or helping -- the PCs to pursue the quest.

In Combat: Given opportunity, the Grey Men will begin combat with a barrage of ranged attacks, magical and mundane. Once combat has closed to melee range, Verrum is the main combatant, preferring to flank opponents to do sneak attack damage, or simply grab them and stab them one at a time. Kazmeth and Oparn will try to keep other opponents occupied while Verrum works, and keep them off Wuller and Sarm.
When the fight is nearly won, Verrum will always switch to grappling the last opponents. Wuller will usually stop shooting and help, joining the grapple and freeing up Verrum to deal sneak attack damage. They will not normally pursue or harass retreating enemies.
Once the fight is over, Oparn can usually be found ministering to the dead and wounded, if they're humanoid. Verrum will seek to recover any knives he threw, and will grant mercy to injured enemies if Oparn doesn't stop him. Wuller and Kazmeth sit aside; Sarm usually tries to hold onto the last traces of the thrill using magic gives him.

In Town: Kazmeth and Wuller will pick up the local news when the party enters a settlement. The Grey Men will then generally spend a few days helping the locals get things together before moving on. They will almost never leave the region affected by whatever disaster ruined their own lives, and so their help is always welcomed. Oparn, naturally, offers his services as a healer. Kazmeth will entertain the townsfolk, sometimes helped by a show of skill from Verrum. Unless something more useful presents itself, Wuller will simply spend his time being sociable in the taproom of the local inn. Sarm, strangely, will spend most of his time with children, showing them magic and teaching them from his broad knowledge. He tends to become taciturn if any but children come to watch him, however.

In the Wild: This is where the Grey Men spend most of their time, wandering from town to town. Wuller keeps the party fed by hunting, supplemented with bought supplies. Sarm will create a tiny hut to shelter them at night.
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Kazmeth of the Sorrows
Bard 6
Size/Type: Medium Humanoid (Elf)
Hit Dice: 6d6 (23hp)
Initiative: +4
Speed: 30ft (6 squares)
Armor Class: 10, touch 10, flat-footed 10
Base Attack/Grapple: +4/+4
Attack: Shortspear +4 melee (1d8/19-20) or longbow +4 ranged (1d8/×3; 100ft)
Full Attack: Shortspear +4 melee (1d8/19-20) or longbow +4 ranged (1d8/×3; 100ft)
Space/Reach: 5ft/5ft
Special Attacks: None
Special Qualities: Elven traits, bardic knowledge 10, countersong 6/day, fascinate 6/day, inspire courage +1 6/day, inspire competence 6/day, suggestion
Saves: Fort +2, Ref +5, Will +6
Abilities: Str 10, Dex 10, Con 10, Int 14, Wis 13, Cha 17
Skills: Bluff +12, Concentration +4, Diplomacy +18, Gather Information +14, Hide +4, Knowledge (history) +7, Knowledge (local) +7, Listen +2, Perform (pipes) +12, Perform (singing) +15, Search +2, Sense Motive +12, Spot +2
Feats: Improved Initiative, Negotiator, Skill Focus (Perform [singing])
Alignment: Neutral Good

Spells Per Day: 4/4/3
Spells Known:
0: daze, flare, light, lullaby, read magic, resistance
1: feather fall, hypnotism, identify, sleep
2: detect thoughts, eagle's splendor, scare

Equipment:

Age: 132
Height and Weight: 5'5", 145lb
Appearance:
Languages: Common, Elven, Draconic, Sylvan.

Once a singer with a travelling circus, Kazmeth now swears he will sing only sad songs until the day he dies. Having lived for many years among humans, he has drunk deeply of the sorrows of their brief lives. He has a voice and a set of pipes that seem equally out of tune until they play one of his sad, sad songs.
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Oparn the Penitent
Cleric 6
Size/Type: Small Humanoid (Gnome)
Hit Dice: 6d8+3 (33hp)
Initiative: +1
Speed: 20ft (4 squares)
Armor Class: 12 (+1 Dex, +1 size), touch 12, flat-footed 11
Base Attack/Grapple: +4/+4
Attack: Quarterstaff +5 (1d4)
Full Attack: Quarterstaff +1/-3 (1d4/1d4)
Space/Reach: 5ft/5ft
Special Attacks: Turn undead 5/day (+2 synergy to turning check)
Special Qualities: Gnome traits
Saves: Fort +5, Ref +3, Will +8
Abilities: Str 11, Dex 12, Con 10, Int 10, Wis 17, Cha 14
Skills: Concentration +4, Craft (alchemy) +2, Heal +17, Hide +4, Knowledge (religion) +5, Listen +2, Survival +2
Feats: Self-Sufficient, Skill Focus (Heal), Toughness
Alignment: Lawful Good

Spells Per Day: 5/4+1/4+1/3+1
Spells Prepared:
0: create water, detect magic, guidance, mending, purify food and drink
1: bless, divine favor, endure elements, detect evil, sanctuary*
2: aid, hold person, lesser restoration, silence, shield other*
3: dispel magic, prayer, summon monster III, protection from energy*
Spell-like Abilities: 1/day—speak with animals (burrowing mammal only, duration 1 minute), dancing lights, ghost sound, prestidigitation. Caster level 1st; save DC 12.

Domains: Healing (cast healing spells at +1 caster level), Protection (grant protective ward once per day)

Equipment:

Age: 82
Height and Weight: 3'5", 35lb
Appearance:
Languages: Common, Gnome.

Oparn was a temple healer, but they say he went a little mad when he could no longer keep up with the endless dead and dying with which he was faced. Every prayer he utters is tinged with fervent regret, and yet he only seems to slip further away with every wound he treats; it is his penance, seeking redemption for simply existing while so many died.
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Verrum Knifer
Rogue 6
Size/Type: Medium Humanoid (Half-Orc)
Hit Dice: 6d6+6 (29hp)
Initiative: +3
Speed: 30ft (6 squares)
Armor Class: 13 (+3 Dex), touch 13, flat-footed 10
Base Attack/Grapple: +4/+11
Attack: Dagger +8 melee (1d4+3/19-20) or dagger +8 ranged (1d4+3/19-20; 10ft)
Full Attack: Dagger +8 melee (1d4+3/19-20) or dagger +8 ranged (1d4+3/19-20; 10ft)
Space/Reach: 5ft/5ft
Special Attacks: Sneak attack +3d6
Special Qualities: Darkvision 60ft, orc blood, evasion, trapfinding, trap sense +2, uncanny dodge
Saves: Fort +3, Ref +8, Will +1
Abilities: Str 16, Dex 16, Con 12, Int 12, Wis 8, Cha 8
Skills: Disable Device +10, Escape Artist +8, Hide +12, Jump +7, Knowledge (local) +5, Move Silently +12, Open Lock +12, Search +10, Sleight of Hand +12, Tumble +7, Use Magic Device +3
Feats: Improved Grapple, Improved Unarmed Strike, Weapon Focus (dagger)
Alignment: Chaotic Good

Equipment:

Age: 24
Height and Weight: 5'2", 174lb
Appearance:
Languages: Common, Orc.

Unlike the ones he travels with, nobody knows what Verrum did with his life, back when he had one. Everyone has their guesses, of course, and if you seem him get angry and pull a knife, you might start to wonder too.
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Blind Wuller
Expert 2/Fighter 4
Size/Type: Medium Humanoid (Human)
Hit Dice: 2d6+4d10+6 (37hp)
Initiative: +2
Speed: 30ft (6 squares) [Blind: moves at three quarters of base speed]
Armor Class: 12 (+2 Dex), touch 12, flat-footed 10
Base Attack/Grapple: +5/+7
Attack: Composite longbow +6 ranged (1d8+2/×3; 110ft)
Full Attack: Composite longbow +4/+4 ranged (1d8+2/×3; 110ft)
Space/Reach: 5ft/5ft
Special Attacks: None
Special Qualities: Blind
Saves: Fort +5, Ref +3, Will +7
Abilities: Str 14, Dex 14, Con 12, Int 8, Wis 16, Cha 10
Skills: Craft (bowmaking) +8, Gather Information +5, Handle Animal +5, Listen +10, Move Silently +7, Survival +4, Use Rope +6
Feats: Blind-Fight, Dodge, Mobility, Point Blank Shot, Precise Shot, Rapid Shot, Skill Focus (Listen)
Alignment: Neutral Good

Equipment:

Age: 27
Height and Weight: 6'3", 210lb
Appearance:
Languages: Common

Such an oddity -- blind man, bowyer, hunter. Wuller says he was blessed with blindness so he wouldn't have to see the world fall apart around him. But he hears -- oh, he hears it.
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Sarm Scriven
Wizard 6
Size/Type: Medium Humanoid (Human)
Hit Dice: 6d4+6 (22hp)
Initiative: +1
Speed: 30ft (6 squares)
Armor Class: 11 (+1 Dex), touch 11, flat-footed 10
Base Attack/Grapple: +3/+3
Attack: Dagger +3 melee (1d4/19-20)
Full Attack: Dagger +3 melee (1d4/19-20)
Space/Reach: 5ft/5ft
Special Attacks: None
Special Qualities: None
Saves: Fort +5, Ref +3, Will +5
Abilities: Str 11, Dex 12, Con 13, Int 18, Wis 11, Cha 9
Skills: Concentration +10, Decipher Script +13, Forgery +7, Knowledge (arcana) +9, Knowledge (architecture and engineering) +7, Knowledge (geography) +5, Knowledge (history) +7, Knowledge (nobility and royalty) +6, Knowledge (the planes) +8, Profession (scribe) +4, Spellcraft +15
Feats: Combat Casting, Craft Wand, Eschew Materials, Extend Spell, Scribe Scroll, Spell Mastery (charm person, explosive runes, knock, suggestion)
Alignment: Neutral Good

Spells Per Day: 4/4/4/3
Spells Prepared:
0: daze, ghost sound, prestidigitation, resistance
1: cause fear, charm person, magic missile, sleep
2: hideous laughter, knock, extended mage armor, summon swarm
3: fireball, suggestion, tiny hut

Familiar: Cerrigan (Rat; Tiny Magical Beast)
Int 8, +3 natural armor, improved evasion, share spells, empathic link, deliver touch spells, speak with master
Sarm gains the Alertness feat (+2 to Listen and Spot) when Cerrigan is in arm's reach.

Equipment:

Age: 38
Height and Weight:
Appearance:
Languages: Common, Draconic, Elven, Gnome.

Even Oparn calls Sarm crazy. Kazmeth knew him back when he worked in a library, but all that's left of the knowledge that library contained is in Sarm's mind -- and maybe in the random dialogues he has with himself on occasion. He also can't seem to go an hour of the day without handling magic, like a plaything, like a beloved child, like a tenuous link to the world around him.
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Design Notes: It's probably a bad sign that I feel the need to explain myself, but here goes anyway. These characters all represent different reactions to despair. Kazmeth is simple melancholy. Oparn represents self-loathing. (No, I didn't choose to make him a gnome because people hate gnomes. Honest!) Verrum is anger directed towards others. Wuller is acceptance, in a way; since he was born blind, he's better able to deal with his circumstances than the others. Sarm is quite simply insane.

I should point out that these five 'types' aren't something I got from a list, like the Five Stages of Grief or whatever. I didn't even have them in mind when I first made up the characters; they just grew out of the party I put together, keeping my theme of 'despair' in mind.
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So there you have it, one big mawkish contest idea that sort of hit me shortly after I read the announcement. No humour awards coming this way. :P