I have 3 so far, an Archer, Assassin (stealth, knife and pickpocket for poisons etc) and a dual wield.

I tried a pure mage but somehow, I find the magic in this game a bit on the lame side compared to weapons, especially at low levels. Also, narrow dungeons don't allow kiting well enough to do it without one hand having a heal or plenty of health pots and multiple opponents often means a quick death. Tried being a stealth mage but a huge fireball or iceball tends to give your position away unlike arrows and the Fire Atronach and Summoned Wolf are pathetically weak on their own.

This thread inspired me to play my Dunmer for a little while. I've decided to make her a paragon of compassion instead of an assassin.

Would be interesting to see how you deal with the Dark Brotherhood quests or any other kill xxxx quest if it comes to that. Or do you pick and choose who gets your compassion?

A fun character would be non lethal who could arrest and drag bad guys back alive for the town guard or Brotherhood to deal with as they see fit. It's up to them if they kill the bad guys as long as you don't.

I always joke that if I were a real-world leader, I'd be a dictator and behead those who actually deserved it... So compassionate to innocents, and vengeful towards those who seek to disrupt peace in Skyrim. >:}

Darq'Raze: Khajiit Thief/Bard/Merchant
Geist: Imperial Nightingale
Malus Snowshield: Nord Warrior
Shiira: Orc Ranger/Hunter
The Mercenary: Redguard Warrior
Legate Brutus: Imperial Warrior
Auditor Camoran: Altmer Mage/Cultist
Umbra: Orc Warrior
Shaman Nokwitz: Orc Shaman
Harlequin: Breton Assassin/Bard
Lord Dare Lance: Dunmer Vampire Nightblade
Dier'Mundra: Bosmer Hunter (Hunting Toon)
Frosty: Falmer (Dunmer as placeholder)
Drake Malice: Breton Vampire Assassin
Arbiter: Altmer Warrior
Mavomee Gitskwisha: Orc Warrior
Prisoner: Imperial Serial Killer
Konahrik: Breton Battlemage
Markus Harrow: Redguard Witchhunter
Lucien Wulf: Nord Barbarian/Lycan
Khorne: Dunmer Battlemage
Raven Beltaine: Breton Battlemage
Dragis Kane: Breton Necromancer
Sir Rayden: Imperial Crusader
Ryuuza: Imperial Warrior/Blade
Amy Raze: Dunmer Warrior
Boba Fett: Imperial Archer (Bounty Hunter obviously)
Ingot the Shattered: Bosmer Warrior
Alandros Protius: Imperial Scout/Archer
Thane Shinoda: Argonian Archer/Warrior/Assassin
Lilith Rayne: Breton Thief/Assassin Vampire
Jakk Raze: Redguard Pirate

I am sure i will have 20 more by the time i retire from Skyrim

I have read a decent amount of your build posts, and figured you have too many character syndrome as I do.

TBH i think Bethesda never meant for Skyrim to be played using multiple characters. (Okay maybe 3 - 4 types if you do roleplaying but not as much as 30+)

Their system in Skyrim in design was meant to cater to players who liked to say play "fighter type" in the beginning, then maybe switch to "stealth style",
then maybe "abit of magic" or even a mix of combos. The idea is not to penalize anyone who had a wrong "build" because there shouldn't be any "correct" build.
If people are creating 30+ characters, i think they have failed in this regards and should think about why are pple creating multiple chars then.

Why do you guys have so many characters? Is it because of roleplay?

I personally only have 2 chars so far as per my sig, (Circea and Illucia)
First one Circea is a lawful good strictly for magic/doing main quest and generally being a nice person overall.
Second one Illucia is a lawful evil Bi**h for doing ALL SORTS of evil nasty stuffs(thief/db).
I still haven't done the Companion quest, and i'll probably be creating a 3rd one just to play it. probably a guy like the Skyrim poster guy.

I have lots of ideas and imagination. Those who have very few characters arent getting the full breadth of Skyrim and lack creativity

Prisoner huh. Think I'm going to try a playthrough where I get a warrant in all holds and if I can't fight my way away from the cops then I will let them haul me away to prison so I can escape to run another day.

Actually my Prisoner wears Ragged Clothes and the Execution Hood and uses a Shiv...it is very murderous looking

Why are you wearing that silly bunny suit?
Why are you wearing that stupid man suit?
what a great movie...

and i've controlled my "to many characters syndrome" i'm down to 2