Though I have burned throught at least 12 characters that I can recall, my favourite by far was my wandering scholar.  An alchemist by trade and with no real combat skills, she relied on the arts of illusion and of course the help from her companions to save her from the dangers that lie throughout the underworld that be Skyrim.  She sought alchemical ingredients to make the most powerful and useful potions that the land had ever seen, making her a well-known apothecary to the people that needed her the most--soldiers, adventurers, and the like.  But most of all, she sought knowledge.  To translate and record all of the word walls known--and unknown--in the land and share the knowledge with fellow scholars.

Breton, Legendary Difficulty.  Master of Illusion, Alchemy, and Speech.  Minor skills are Restoration and Sneak.

By far my most difficult character, and every encounter was like a puzzle to try and solve since she had no real damage-dealing skills.  Also ran into quite a few "glitches" where the main objective of the quest had to be dealt the killing blow by you and you alone, and not by people you had frenzied or followers or anything else (or else they would do the "dying stance" for 10 seconds then come back up at full health).  Not to mention dragons had to be pulled into towns to actually kill them.  So some console had to be used to progress...  But I refused to let the game's mechanics dictate how my character should be played.  ^_^

My first character was a Nord whos name was Arthas I dunno why I called him Arthas for the reason? i got 2 saved files for him one of him being a shield and sword warrior with werewolf form while the other is the same but vampire version, i also have an orc who I haven't played much but will soon to maybe a powerhouse tank

I have many characters simply because I am trying to find the right battle style for me. The first Skyrim character I ever made was actually on brother's friend's XBox.

She was Khajit named Titania and she stole things only from bandits. I never got too far with her.

I revived Titania into an argonian on my friend's PS3 when I moved into the college dorms. Unfortunately, I messed up with her when doing the main quest and had to delete her. Being a noob I thought I gave all the supplies I needed to the wood elf, but I didn't. I was underleveled and had nothing to my name. She was going to be a theif.

The character that is my current favorite to play is Kha'Ahni. She is also Khajit. I'm using a werewolf mod with a silver ring so she shifts every full moon. I prefer it that way. She will eventually join the theives guild, brotherhood, and companions (then become ex-companion to go to the dark side) I want to complete the main quest with her first before I join any guilds and the like.

It is also for roleplay. Kha'Ahni begins to descend into madness after the defeat of Alduin. She wants to prove that she is a good person so she goes to the companions, but then slowly insanity hits and she joins the theives guild. In search of more power she eventually joins the Brotherhood as well.

Kha'Ahni also almost has her sneak maxed out.

I also have  High Elf. I'm not to far with her so its not worth mentioning.

Katyusha is an argonian knight. She is very into the white knight thing. She joins the imperials and then after the civil war she will join the companions to continue doing good. She will cure herself of lycanthropy (I think its weird to have a lizard go wolf but I guess the same could be said for a cat, no?)

I have dawngaurd, but I don't know how much I want my characters to go into it. I mainly got it for the perks in lycanthropy, as well as for my high elf that I want to become a vampire.

Those are my main characters.

My main character is Tatsu R. Bay! Master of the sword and shield and wearer of the light armor. I also use the bow and arrow pretty often and sneak when needed. I also don't use magic unless I REALLY need to. I'm also a good natured person. I believe that sums up my character.

~Tatsu

I have four characters, and because I'm fairly obsessed with roleplaying, they all have backstories and complex personalities. In the order that they were created in, they are:

J'shana, a female Khajiit. She's in my profile pic.  She's calm, deep-thinking and sensitive, and is a very skilled stealth archer and alchemist. She's an honourable character but joined the Thieves Guild because she needed to hide from the Thalmor (for complicated backstory reasons.) She lives a double life - half with the Guild, the other half defending Skyrim from dragons and vampires, and is married to Derkeethus.

Jeerala, a female Argonian. She has absoloutely no common sense, tries to make friends with everyone (including things you really shouldn't try to make friends with, such as Draugr) and is terrified of spiders. She's a talented mage, favouring Destruction and Conjuration, and is married to Onmund. She's also a member of the Dawnguard.

Ozan, a male Redguard vampire. He's got no surviving family and a troubled past, and if he has a 'remain silent' option, he always takes it. In my headcanon, he hardly ever talks, except in monosyllables. He dual-wields swords, is a skilled assassin, and is the Listener as well as a vampire lord. He's married to Jenassa. He thinks little of killing, but he actually has strong morals and never goes too far. (For example, he refused to kill Nilsine Shatter-Shield because he thought her family had been through enough.)

Arvenrior, a male Altmer warrior. He was orphaned young and brought up by Nords, and so he lives like a Nord - wielding greatswords, wearing heavy armour, joining the Stormcloaks and Companions, etc. He's not married yet, but I reckon he will marry Lydia. He's shy, modest, and worships Talos. Yes, I basically made him to shun every Altmer stereotype. :)

I will stop there before I can write an essay on my characters' pasts and motivations. Because then we'd be here about five years.

The character I currently have on the XBox is:

Ma' Bokah: Khajiit, Harbinger, Dawnguard member, Destroyer of the Dark Brotherhood, Champion of Namira and Hircine, Werewolf, Warrior, skilled in Heavy Armor, Two-Handed and One-Handed (Also, i mostly use my claws. They're better than any weapon i currently have.) He's tough, smart, and sometimes uses sort-of-funny one liners.

If i'm correct, he's currently using the Blades gauntlets with the Savior's Hide, the Ring of Hircine, the Amulet of Talos, and i think fur boots.  

My backstory for him is that he came to Skyrim seeking fortune and fame, and joined the Companions. Eventually he became Harbinger, joined the Dawnguard, destroyed the Dark Brotherhood, discovered he was Dragonborn, and became the Champion of two Daedric Princes. Just the fame he was looking for. 

I am a Breton that usually is a one-handed shield warrior. My name is Cody and my first leader role was the head of the Thieves Guild. Then, Arch-Mage, The Listener and last, Harbinger. I joine dthe Stormcloaks because I felt a connection with them. Most of what they said, I felt was true and the banishment of Talos was a violation of natural rights. Freedom of Religion. I compleated the rebellion and my Dragonborn training. Although the one thing I actually came to regret, was the murder of out wonderful Administrator. I stopped playing for 3 straight days because I felt bad. I started a new game on another account to try to repent and hope that I would be forgiven. I now look at my previous character as a monster, wearing Deadric armor. Not really proud, but my only wish now is that I can be forgiven. -Lorotonikaan

Paarthurnax, if you are reading above, please forgive me. :(

I have burned through 72 characters but I am most proud of my current one

In two weeks he has become level 138 (all skills maxed)  Killed alduin, learned every shout done all of the dlcs and completed all of the factions questline and became thane of all of the holds all on ledgendary difficuty. And I've completed all of the Daedric quests

Argonian

Name: Benjamin the Heartless

Gender: Male

Race: Nord

Occupation: Notorious Mercenary

Weapon Type: Two-Handed

Armor: Heavy

Notes: High Smithing and Two-Handed skills.

DovaKiinZaan

I have burned through 72 characters but I am most proud of my current one

In two weeks he has become level 138 (all skills maxed)  Killed alduin, learned every shout done all of the dlcs and completed all of the factions questline and became thane of all of the holds all on ledgendary difficuty. And I've completed all of the Daedric quests

Argonian

Impressive! What do you do now?

Currently I have only one character, but have gone through at least 100, most of which never beat Alduin.

He is Uthor Moorwing, the Breton. He was a Vigilant of Stendarr, but they stripped him of his powers and memories when he began to use dark magic to dispatch evil. He has a strong hate for undead, but doesn't care if he needs Daedric Artifacts to win. He joined the Dawnguard as soon as he heard about them, and quickly developed the Pyre Crossbow, a weapon constantly remade as his smithing and enchanting increase. He has a strong bond with Serana, and will put himself in harms way to protect her. He recently regained his memories after the removal of a seal on his face (tattoo) .

But I will never forget my first character. Yin, the Argonian. He defeated Alduin, joined all the factions, and got all the artifacts. He was my proud, heroic, revered, loved and compassionate experience-it-all character. Sadly, at level 82, a save glitch corrupted his save file. I made him over the course of half an hour of tedious character creation, and clocked 200 hours in as him. I will never get that back. He is gone forever, and with him, 200 hours of my life. But with him I got to experience Skyrim for the first time. My first RPG on a "modern" console (Yes, I know ps3 is outdated now, but still). I killed dragons. Freaking. Dragons. I was giddy, drunk on power and Sanguine's special brew. I miss him. But my time with him were the best 200 hours of my life. Rest in peace, Yin the Dovahkiin. 

My current character is an Imperial named Bregiir. He is mostly a sword-and-board  fighter but is not afraid to pull out a candlelight or healing spell once in a while! Loyal to Cyrodiil, his birthplace, Bregiir supports the Empire in the civil war. However, Thalmor are on his hitlist, so any lone Altmer ought to mind their tongue and watch their backs.

Oh I've had a ton.

My first was a redguard but I don't remember his name.

My current is a nord named Ivar Fjord-Winter. He is mainly a heavy armor-sword-conjuration mage.

The one I got highest level with was a High Elf named Lenthir, level 95. He was my first character with the legendary edition. He was a light armor-sword-restoration mage.

My current file (and hopefully only one) is a male Dunmer that looks like a Dwemer (the same eye and skin color). He has Daedric armor (Legendary) with Konahrik (Legendary); and for clothing (when not in a fight) he wears Vampire Royal Armor, Vampire Gauntlets, Vampire Boots, and the Aetherial Crown. Currently, I am level 26 (I have maxed out smithing). For weapons he uses a Dragonbone sword (Legendary), until I defeat Miraak, then he will use Miraak's sword (Legendary). Sides I am on (and and will soon join): Companions, Imperials (they aren't racist towards the Dunmer), Dawnguard, Dark Brotherhood, and Thieves Guild. My goals are: Master Destruction, Master Conjuration, Master ALL other skills, buy house in Raven Rock, No Legendary Skills (so Maximum will be Level 81), Get All Thu'ums, and A LOT MORE (Too Many To List)!!!!!!