How to create a character with the same combat flavour as the Viper (Game of Thrones)?

Question

I recently started my first DnD campaign and decided to go for the Swordsage from the Tome of Battle. The way I imagine my character fighting is like Prince Oberyn from Game of Thrones (be warned: the video is graphic, and contains spoilers if you're not up to date with the series).

How can I create a functional character in DnD 3.5e that fights like the Viper?

It doesn't need to be perfectly optimized or exactly like him. Basically, I want to be able to dance around my opponents, take as little hits as possible and look cool while I cause as many opponents as possible some trouble. In return I'm willing to not do all that much damage and to be in quite some trouble if I do get hit a few times. I don't want to miss out on a superb maneuver just because it doesn't quite fit the flavour though. Likewise, I'm not going to use a terrible skill because it fits the style.

For now I have a level one Swordsage with Desert Wind as a discipline focus, fighting with a spear and using the Child of Shadow stance. I have leather armor, relatively low strength. And am using maneuvers like Burning Blade, Clinging Shadow, Sudden Leap and Distracting Ember.

You don't need to stick to this build at all in your answer though. You can even use different classes (Not necessarily from ToB).

Be sure to point out which elements of a build are a must for it to function and which are for flavour.

Answer 1

I literally played a character named Oberyn Martell in a gladiator-style arena game that a friend ran. He was the only undefeated gladiator in the game. Note, however, that the game started from 1st, all XP had to be earned in the arena, and you were not allowed to enter with any buffs active. It also had very low stats, and quite a few houserules. The character was optimized for that situation.

Oberyn, Pit Fighter

Master of Poisons from Drow of the Underdark was the first key. In this situation, Barbarian 1 was close to being the correct level to take, because of the d12 HD and the big bonus to Constitution. But a barbarian doesn’t have a lot of options other than “hit it,” and that left too much up to chance. Careful selection of poisons allowed me to stack things very much in my favor. Arsenic and Old Lace is by-far the best guide available to making the most of poison. Sleep-smoke (Waterdeep, City of Splendors) and roach paste (Drow of the Underdark) were my personal favorites.

Like the Red Viper himself, reach was also key. I actually went with a straight longspear; I was worried about being charged, and I had terrible Int, so I wasn’t worried about tripping. I also wound up taking a level of swordsage, and the longspear is a Desert Wind weapon, allowing me to get the Discipline Focus benefit while using it.

Fer-de-Lance, i.e. Oberyn Mk. II

I eventually retired Oberyn, and ran a revamped build that focused heavily on Charisma (since it affected the favors you received after combat). My build there was Hexblade 2/Bard 1/Cloistered Cleric 1, i.e. a pretty typical Cha-to-everything build. Snowflake Wardance meant Cha-to-attack, Arcane Resistance meant Cha-to-saves-vs-spells, etc. Dynamic Priest let me use Cha for bonus cleric spells.

I again took Master of Poisons, and put sleep-smoke and roach paste to good use.

Reach became an even bigger focus: a level in bard gave whip proficiency, and that allowed me to use a whip-dagger. I also took Aberrant Heritage and Inhuman Reach, just to make that reach crazy-huge. My cleric domain was Animal, just for enlarge person (though without the ability to pre-buff, that never got used; I think I planned to hit crusader and go for ruby knight vindicator).