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I'll start with an easy one and work up. This was a concept requested over at EnWorld that I participated in.

Inigo Montoya - Level 1Show

====== Created Using Wizards of the Coast D&D Character Builder ======
Inigo Montoya, level 1
Human, Rogue
Build: Aerialist Rogue
Rogue Tactics: Artful Dodger
Rogue: Rogue Weapon Talent
Background: Wandering Duelist, Bereaved, Out for Revenge, Wandering Mercenary (Wandering Duelist Benefit)

FINAL ABILITY SCORES
Str 11, Con 10, Dex 20, Int 10, Wis 8, Cha 14.

STARTING ABILITY SCORES
Str 11, Con 10, Dex 18, Int 10, Wis 8, Cha 14.

AC: 17 Fort: 11 Reflex: 18 Will: 13
HP: 22 Surges: 6 Surge Value: 5

TRAINED SKILLS
Streetwise +7, Stealth +10, Thievery +10, Bluff +7, Perception +4, Acrobatics +10, Athletics +5

UNTRAINED SKILLS
Arcana, Diplomacy +2, Dungeoneering -1, Endurance, Heal -1, History, Insight -1, Intimidate +5, Nature -1, Religion

FEATS
Human: Flash of the Blade
Level 1: Weapon Proficiency (Rapier)

POWERS
Bonus At-Will Power: Acrobatic Strike
Rogue at-will 1: Duelist's Flurry
Rogue at-will 1: Piercing Strike
Rogue encounter 1: Acrobat's Blade Trick
Rogue daily 1: Duelist's Prowess

ITEMS
Leather Armor, Adventurer's Kit, Rapier

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Inigo Montoya - Level 26Show

====== Created Using Wizards of the Coast D&D Character Builder ======Inigo Montoya, level 26
Human, Rogue, Blade Bravo, Dragonheart
Build: Aerialist Rogue
Rogue Tactics: Artful Dodger
Rogue: Rogue Weapon Talent
Whirlwind Sneak Attack: Cunning Cyclone
Background: Wandering Duelist, Bereaved, Out for Revenge, Wandering Mercenary (Wandering Duelist Benefit)

FINAL ABILITY SCORES
Str 15, Con 14, Dex 27, Int 12, Wis 10, Cha 20.

STARTING ABILITY SCORES
Str 13, Con 10, Dex 18, Int 10, Wis 8, Cha 13.

AC: 40 Fort: 31 Reflex: 39 Will: 34
HP: 151 Surges: 8 Surge Value: 37

TRAINED SKILLS
Streetwise +23, Stealth +26, Thievery +26, Bluff +23, Perception +18, Acrobatics +31, Athletics +25

UNTRAINED SKILLS
Arcana +14, Diplomacy +18, Dungeoneering +13, Endurance +15, Heal +13, History +14, Insight +13, Intimidate +21, Nature +13, Religion +14

FEATS
Human: Flash of the Blade
Level 1: Weapon Proficiency (Rapier)
Level 2: Irrefutable Blade
Level 4: Red Cloak Student
Level 6: Red Cloak Rake
Level 8: Weapon Focus (Light Blade)
Level 10: Weapon Expertise (Light Blade)
Level 11: Frantic Recovery
Level 12: Slaying Action
Level 14: Persistent Threat
Level 16: Duelist's Panache
Level 18: Swift Footwork
Level 20: Agile Athlete
Level 21: Backstabber
Level 22: Whirlwind Sneak Attack
Level 24: Long Step
Level 26: Superior Initiative

POWERS
Bonus At-Will Power: Acrobatic Strike
Rogue at-will 1: Duelist's Flurry
Rogue at-will 1: Piercing Strike
Rogue encounter 1: Acrobat's Blade Trick
Rogue daily 1: Duelist's Prowess
Rogue utility 2: Agile Footwork
Rogue encounter 3: Flamboyant Strike
Rogue daily 5: Duelist's Demand
Rogue utility 6: Swift Parry
Rogue encounter 7: Pinning Blade
Rogue daily 9: Rogue's Recovery
Rogue utility 10: Gap in the Armor
Rogue encounter 13: Cunning Cyclone (replaces Acrobat's Blade Trick)
Rogue daily 15: Wounding Strike (replaces Duelist's Prowess)
Rogue utility 16: Denying Stance
Rogue encounter 17: Path of the Blade (replaces Flamboyant Strike)
Rogue daily 19: Feinting Flurry (replaces Duelist's Demand)
Rogue utility 22: Scoundrel's Epiphany
Rogue encounter 23: Knave's Gambit (replaces Pinning Blade)
Rogue daily 25: Cruel Pursuit (replaces Rogue's Recovery)

ITEMSAdventurer's Kit, Rapier, Starleather Armor

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Note about Fezzik - his mace is actually him just punching stuff. Assume he uses it two-handed unless he's making an attack that requires a hand free.

Fezzik - Level 1Show

====== Created Using Wizards of the Coast D&D Character Builder ======Fezzik, level 1
Goliath, Fighter
Build: Brawling Fighter
Fighter: Combat Superiority
Fighter Talents: Brawler Style
Background: Wandering Mercenary, Occupation - Criminal, Occupation - Entertainer, Muscle, Occupation - Thug, Former Gladiator (Wandering Mercenary Benefit)

FINAL ABILITY SCORES
Str 19, Con 16, Dex 14, Int 8, Wis 10, Cha 10.

STARTING ABILITY SCORES
Str 17, Con 14, Dex 14, Int 8, Wis 10, Cha 10.

AC: 15 Fort: 18 Reflex: 12 Will: 11
HP: 31 Surges: 12 Surge Value: 7

TRAINED SKILLSIntimidate +5, Endurance +8, Athletics +11

UNTRAINED SKILLS
Acrobatics +2, Arcana -1, Bluff, Diplomacy, Dungeoneering, Heal, History -1, Insight, Nature +2, Perception, Religion -1, Stealth +2, Streetwise, Thievery +2

FEATS
Level 1: Improved Grab

POWERS
Fighter at-will 1: Knockdown Assault
Fighter at-will 1: Grappling Strike
Fighter encounter 1: Bell Ringer
Fighter daily 1: Brute Strike

ITEMS
Mace, Leather Armor

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Fezzik - Level 26Show

====== Created Using Wizards of the Coast D&D Character Builder ======
Fezzik, level 26
Goliath, Fighter, Stoneblessed, Eternal Defender
Build: Brawling Fighter
Fighter: Combat Superiority
Fighter Talents: Brawler Style
Background: Wandering Mercenary, Occupation - Criminal, Occupation - Entertainer, Muscle, Occupation - Thug, Former Gladiator (Wandering Mercenary Benefit)

FINAL ABILITY SCORES
Str 28, Con 23, Dex 16, Int 10, Wis 12, Cha 12.

STARTING ABILITY SCORES
Str 17, Con 14, Dex 14, Int 8, Wis 10, Cha 10.

AC: 36 Fort: 45 Reflex: 31 Will: 30
HP: 203 Surges: 15 Surge Value: 50

TRAINED SKILLS
Intimidate +22, Endurance +24, Athletics +29

UNTRAINED SKILLSAcrobatics +16, Arcana +13, Bluff +14, Diplomacy +14, Dungeoneering +14, Heal +14, History +13, Insight +14, Nature +16, Perception +14, Religion +13, Stealth +16, Streetwise +14, Thievery +16

FEATS
Level 1: Improved Grab
Level 2: Natural Intimidator
Level 4: Goliath Crusher
Level 6: Marked Fury
Level 8: Power Attack
Level 10: Inescapable Hold
Level 11: Legacy of WarLevel 12: Unyielding Stone
Level 14: Clobbering Brawler
Level 16: Crushing Pin
Level 18: Grit
Level 20: Striking Resurgence
Level 21: Crushing Grab
Level 22: Toughness
Level 24: Bludgeon Mastery
Level 26: Epic Fortitude

POWERS
Fighter at-will 1: Grappling Strike
Fighter at-will 1: Knockdown Assault
Fighter encounter 1: Bell Ringer
Fighter daily 1: Brute Strike
Fighter utility 2: Full Extension
Fighter encounter 3: Sweeping Blow
Fighter daily 5: Rain of Steel
Fighter utility 6: Everybody Move
Fighter encounter 7: Come and Get It
Fighter daily 9: One Against Many
Fighter utility 10: Snap Out of It
Fighter encounter 13: Bash and Pummel (replaces Bell Ringer)
Fighter daily 15: Relentless Headlock (replaces Brute Strike)
Fighter utility 16: Bolstering Stride
Fighter encounter 17: Buffeting Torque (replaces Sweeping Blow)
Fighter daily 19: Reaving Strike (replaces Rain of Steel)
Fighter utility 22: Act of Desperation
Fighter encounter 23: Warrior's Urging (replaces Come and Get It)
Fighter daily 25: Reaper's Stance (replaces One Against Many)

ITEMS
Mace, Starleather Armor, Brimstone Cloak +5
====== Copy to Clipboard and Press the Import Button on the Summary Tab ======

And the man with the plan...Vizzini - Level 1Show

====== Created Using Wizards of the Coast D&D Character Builder ======Vizzini, level 1
Gnome, Bard
Build: Cunning Bard
Bardic Virtue: Virtue of Cunning
Background: Occupation - Criminal, Brains, Recent Life - Mercenary Work, Wandering Mercenary (+2 to Bluff)

FINAL ABILITY SCORES
Str 8, Con 10, Dex 10, Int 19, Wis 11, Cha 18.

STARTING ABILITY SCORES
Str 8, Con 10, Dex 10, Int 17, Wis 11, Cha 16.

AC: 17 Fort: 10 Reflex: 16 Will: 15
HP: 22 Surges: 7 Surge Value: 5

TRAINED SKILLS
Arcana +13, History +11, Religion +11, Bluff +11, Diplomacy +9

UNTRAINED SKILLS
Acrobatics +1, Dungeoneering +3, Endurance +1, Heal +1, Insight +1, Intimidate +5, Nature +3, Perception +1, Stealth +3, Streetwise +7, Thievery +1, Athletics

FEATS
Bard: Alchemist
Level 1: Bardic Knowledge

POWERS
Bard at-will 1: Vicious Mockery
Bard at-will 1: Cutting Words
Bard encounter 1: Blunder
Bard daily 1: Malevolent Mischief

ITEMS
Ritual Book, Adventurer's Kit, Wand Implement, Light Shield, Short sword, Leather Armor
FORMULAS
Antivenom, Clearsense Powder

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Vizzini - Level 26Show

====== Created Using Wizards of the Coast D&D Character Builder ======
Vizzini, level 26
Gnome, Bard, Silver-Tongued Scoundrel, Lorekeeper
Build: Cunning Bard
Bardic Virtue: Virtue of Cunning
Background: Occupation - Criminal, Brains, Recent Life - Mercenary Work, Wandering Mercenary (+2 to Bluff)

FINAL ABILITY SCORES
Str 10, Con 12, Dex 12, Int 26, Wis 13, Cha 25.

STARTING ABILITY SCORES
Str 8, Con 10, Dex 10, Int 17, Wis 11, Cha 16.

AC: 41 Fort: 29 Reflex: 38 Will: 36
HP: 149 Surges: 8 Surge Value: 37

TRAINED SKILLS
Arcana +31, History +29, Religion +29, Bluff +30, Diplomacy +27, Stealth +21, Nature +21

UNTRAINED SKILLS
Acrobatics +22, Dungeoneering +18, Endurance +18, Heal +18, Insight +18, Intimidate +24, Perception +18, Streetwise +24, Thievery +18, Athletics +21

FEATS
Bard: Alchemist
Learned Spellcaster: Ritual Caster
Level 1: Bardic Knowledge
Level 2: Bard of All Trades
Level 4: Friendly Deception
Level 6: Alertness
Level 8: Jack of All Trades
Level 10: Linguist
Level 11: Skill Power
Level 12: Mark of Scribing
Level 14: Skill Focus (Arcana)
Level 16: Skill Focus (Bluff)
Level 18: Skill Focus (History)
Level 20: Skill Focus (Religion)
Multiclass Mastery: Learned Spellcaster
Multiclass Mastery: Twilight Adept
Level 21: Multiclass Mastery
Level 22: Adept Power
Level 24: Arcane Mastery
Level 26: Duelist's Panache

POWERS
Bard at-will 1: Vicious Mockery
Bard at-will 1: Cutting Words
Skill Power: Stall Tactics
Bard encounter 1: Blunder
Bard daily 1: Malevolent Mischief
Bard utility 2: Strategist's Epiphany
Bard encounter 3: Recitation of Foreknowledge
Bard daily 5: Satire of Bravery
Bard utility 6: Confusing Blather
Bard encounter 7: Timely Distraction
Bard daily 9: Hideous Laughter
Bard utility 10: Tactician's Measure
Bard encounter 13: Sharp Retort (replaces Blunder)
Bard daily 15: Hole in the Mind (retrained to Vertigo at Adept Power) (replaces Malevolent Mischief)
Bard utility 16: Elemental Countermeasures
Bard encounter 17: Shout of Evasion (replaces Recitation of Foreknowledge)Bard daily 19: Mocking Epigram (replaces Satire of Bravery)Bard utility 22: Note of AggressionBard encounter 23: Mind Game (replaces Timely Distraction)Bard daily 25: Fraught with Failure (replaces Hideous Laughter)

ITEMSRitual Book, Adventurer's Kit, Wand Implement, Light Shield, Short sword, Starleather ArmorRITUALSComprehend Language, Portend Weather, Seek Rumor, Fool's Gold, Object Reading, Fool's Speech, Memory of a Thousand Deaths, Analyze Portal, Inquisitive's Eyes, Linked Portal, Seal Portal, Status, Magic Map, Scribe, History Revealed, Memory of the Dragon, Reverse Portal, View Location, Consult Oracle, Memory Seal, View Object
FORMULAS
Antivenom, Clearsense Powder

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Wesley - Level 4Show

====== Created Using Wizards of the Coast D&D Character Builder ======
Wesley, level 4
Human, Fighter|Rogue
Hybrid Talent: Rogue Tactics (Hybrid)
Rogue Tactics (Hybrid): Brutal Scoundrel (Hybrid)
Background: Society - Poor, Occupation - Mariner, Blademaster, Pivotal Event - You Die, Recent Life - Valued Prisoner, Recent Life - Mercenary Work (Acrobatics class skill)

FINAL ABILITY SCORES
Str 17, Con 10, Dex 19, Int 12, Wis 8, Cha 12.

STARTING ABILITY SCORES
Str 16, Con 10, Dex 16, Int 12, Wis 8, Cha 12.

AC: 19 Fort: 18 Reflex: 19 Will: 15
HP: 38 Surges: 7 Surge Value: 9

TRAINED SKILLS
Acrobatics +11, Bluff +8, Insight +6, Perception +6, Intimidate +8, Athletics +10

UNTRAINED SKILLS
Arcana +3, Diplomacy +3, Dungeoneering +1, Endurance +2, Heal +1, History +3, Nature +1, Religion +3, Stealth +6, Streetwise +3, Thievery +6

FEATS
Human: Hybrid Talent
Level 1: Weapon Proficiency (Rapier)
Level 2: Flash of the Blade
Level 4: Slaying Action

POWERS
Bonus At-Will Power: Footwork Lure
Hybrid at-will 1: Duelist's Flurry
Hybrid at-will 1: Sure Strike
Hybrid encounter 1: One-Two Punch
Hybrid daily 1: Villain's Menace
Hybrid utility 2: Pass Forward
Hybrid encounter 3: Probing Attack

ITEMS
Leather Armor, Quicksilver Blade Rapier +1

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Wesley - Level 26Show

====== Created Using Wizards of the Coast D&D Character Builder ======
Wesley, level 26
Human, Fighter|Rogue, Sword Coast Corsair, Deadly Trickster
Hybrid Talent: Rogue Tactics (Hybrid)
Rogue Tactics (Hybrid): Brutal Scoundrel (Hybrid)
Background: Society - Poor, Occupation - Mariner, Blademaster, Pivotal Event - You Die, Recent Life - Valued Prisoner, Recent Life - Mercenary Work (Acrobatics class skill)

FINAL ABILITY SCORES
Str 23, Con 12, Dex 25, Int 14, Wis 10, Cha 14.

STARTING ABILITY SCORES
Str 16, Con 10, Dex 16, Int 12, Wis 8, Cha 12.

AC: 39 Fort: 42 Reflex: 43 Will: 37
HP: 165 Surges: 8 Surge Value: 41

TRAINED SKILLS
Acrobatics +25, Bluff +20, Insight +18, Perception +18, Intimidate +20, Athletics +24

UNTRAINED SKILLS
Arcana +15, Diplomacy +19, Dungeoneering +13, Endurance +14, Heal +13, History +15, Nature +13, Religion +15, Stealth +20, Streetwise +15, Thievery +20

FEATS
Human: Hybrid Talent
Level 1: Weapon Proficiency (Rapier)Level 2: Flash of the Blade
Level 4: Unarmored Agility
Level 6: Exotic Fighting Style
Level 8: Irrefutable Blade
Level 10: Toughness
Level 11: Action Recovery
Level 12: Persistent Threat
Level 14: Weapon Focus (Light Blade)
Level 16: Weapon Expertise (Light Blade)
Level 18: Frantic Recovery
Level 20: Bloody Tenacity
Level 21: Robust Defenses
Level 22: Epic Fortitude
Level 24: Epic Reflexes
Level 26: Epic Will

POWERS
Bonus At-Will Power: Disheartening Strike
Hybrid at-will 1: Duelist's Flurry
Hybrid at-will 1: Sure Strike
Hybrid encounter 1: One-Two Punch
Hybrid daily 1: Villain's Menace
Hybrid utility 2: Pass Forward
Hybrid encounter 3: Probing Attack
Hybrid daily 5: Duelist's Demand
Hybrid utility 6: Nimble Climb
Hybrid encounter 7: Dismaying Slash
Hybrid daily 9: Knockout
Hybrid utility 10: Incredible Stride
Hybrid encounter 13: Unbalancing Attack (replaces One-Two Punch)
Hybrid daily 15: Unerring Blow (replaces Villain's Menace)
Hybrid utility 16: Twisting Escape
Hybrid encounter 17: Exorcism of Steel (replaces Probing Attack)
Hybrid daily 19: Feinting Flurry (replaces Duelist's Demand)
Hybrid utility 22: No Surrender
Hybrid encounter 23: Death Dance (replaces Dismaying Slash)
Hybrid daily 25: Fighter's Resurgence (replaces Unerring Blow)

ITEMS
Quicksilver Blade Rapier +1, Starweave Armor, Bracers of Tactical Blows (paragon tier), Cat Paws (paragon tier), Baldric of Valor (epic tier), Ring of Agile Thought (paragon tier), Ring of Action Reversal (paragon tier), Quickstride Boots (paragon tier), Circlet of Continuity (paragon tier), Dice of Auspicious Fortune (paragon tier)

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For Max, I figured I'd put him at the first level in which he can reasonably say he has Raise Dead; so, 8 it is.

Miracle Max - Level 8Show

====== Created Using Wizards of the Coast D&D Character Builder ======Miracle Max, level 8
Dwarf, Cleric
Build: Shielding Cleric
Background: Disgraced, Divinely Inspired, Sage, Surgeon (+2 to Insight)

FINAL ABILITY SCORES
Str 8, Con 13, Dex 10, Int 10, Wis 21, Cha 18.

STARTING ABILITY SCORES
Str 8, Con 11, Dex 10, Int 10, Wis 17, Cha 16.

AC: 15 Fort: 16 Reflex: 15 Will: 22
HP: 60 Surges: 8 Surge Value: 15

TRAINED SKILLS
Religion +9, Insight +16, Heal +14, Diplomacy +13

UNTRAINED SKILLS
Acrobatics +4, Arcana +4, Bluff +8, Dungeoneering +11, Endurance +7, History +4, Intimidate +8, Nature +9, Perception +9, Stealth +4, Streetwise +8, Thievery +4, Athletics +3

FEATS
Cleric: Ritual Caster
Level 1: Pacifist Healer
Level 2: Healer's Implement
Level 4: Pacifist's Reward
Level 6: Shielding Word
Level 8: Defensive Healing Word

POWERS
Channel Divinity: Healer's Mercy
Cleric at-will 1: Astral Seal
Cleric at-will 1: Gaze of Defiance
Cleric encounter 1: Prophetic Guidance
Cleric daily 1: Beacon of Hope
Cleric utility 2: Healer's Gift
Cleric encounter 3: Command
Cleric daily 5: Consecrated GroundCleric utility 6: HaggleCleric encounter 7: Denunciation

ITEMSRitual Book, Cloth Armor (Basic Clothing)RITUALSGentle Repose, Raise Dead