Behold Black Jack Wellesley
, the Dread Pirate King!
One level of Marshal allows him to add his Charisma bonus to allies' Dexterity rolls, 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. 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.)
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 +4 bonus to move silently.When combined with Motivate Dexterity, it allows Black Jack and his crew to sneak around with with catlike tread
Other songs which will be featured when he has to inspire his crew include:
Pirates of Penzance - The Pirate King Song
HMS Pinafore - A British Tar Is A Soaring Soul
Muppet Treasure Island - Shiver Me Timbers
Arrogant Worms - Last Pirate Of Saskatchewan