Phillip is usually the drunk, and Capt Amos is usually the sailor. Sometimes they're both drunk, and sometimes they're both sailors. Every once in a great while they are both drunk and both sailors.
Phillip McGuinness and Captain Amos met in 2005 as cast members of the Kentucky Renaissance Faire. After a couple years of doing improv acting together, they started appropriating unused stages with a guitar and a will to entertain.
Drunk & Sailor has been seen at renaissance festivals from the Gulf Coast to Lake Michigan, sci-fi/fan conventions (including the 2009 DragonCon Pirate Party), and more bars than they can remember (though that may have more to do with the alcohol than the number of bars).