Black Jack Wellesley, the Dread Pirate King!

This is a build I was inspired to make after watching far too many pirate movies.

Black Jack Wellesley is a Bard 3/Marshal 1/Bard 7/Dread Pirate 10

One level of Marshal allows him to add his Charisma bonus to allies' Dexterity based checks and skill checks, including initiative, while nine levels of bard grant him a Inspire Courage of +8 when all feats, spells, and items affecting it are accounted for, as well as Inspire Greatness.

Finishing off the build are ten levels of Dread Pirate (honorable path) which improves Inspire Courage and grants some pretty nifty abilities when using Inspire Courage, such as temporary hit points equal to 10 + Charisma modifier, a dodge bonus to Armor Class equal to Charisma modifier, and the Die Hard feat. Dread Pirate also allows you to take 10 on certain skills, such as Tumble. Black Jack's tumble modifier in armor is +41, which means that he can tumble up a vertical surface if the Epic Tumble rules are used. Sure, a wizard could just cast fly, but that's just not as stylish as breakdancing your way up a castle wall.

Slippers of Battle Dancing allow him to use his Charisma modifier instead of Strength/Dexterity when calculating attack and damage rolls if he has moved 10 feet or more. (They also grant +5 to Tumble and, if you have more than 5 ranks in Perform, +2 to Initiative.)

Imperious Command allows him to severely demoralize people with Intimidate, while Combat Panache gives several useful tactical maneuvers for a Charisma based swashbuckler.

The Bard Mimicking Song ACF replaces Countersong and grants allies a +2 bonus to move silently, which increases by +2 for every 5 bard levels. When combined with Motivate Dexterity, it allows Black Jack and his crew to sneak around with catlike tread.

Other songs which will be features when he has to inspire his crew include:

Pirate King – Pirates of Penzance

Shiver My Timbers – Muppet Treasure Island

Heart of Oak – British Naval Song

The Last Saskatchewan Pirate – Captain Tractor

Fifteen Men on a Dead Man's Chest/Derelict – Robert Louis Stevenson/Young Ewing Allison

(Young Ewing Allison wrote the poem Derelict to complete the fragmentary song Fifteen Men on a Dead Man's Chest found in Robert Louis Stevenson's Treasure Island)