1. SKALLYWAG- a crackhead or crackwhore, one that lives on the streat and bums for money to buy alcohol or drugs. one that will rob an old lady of her purse to get a quick fix.
EX. Tell your skank ass skallywag mom to stop asking me for change before i pimp slap that ho with powder on my hand.
by PIMP S. May 17, 2004
A term used in the old red light districts of Europe, referring to a scoundrel, troublemaker, or outlaw (or a troublemaker even among outlaws).
After his fight with the pirates the week before, Cap'n John had become known as a skallywag; as well as a man who could hold his ale.
by Fawkes August 21, 2004