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
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
Term for when you use cocaine while banging a horse. Commonly practiced in East Tennessee and Nigeria.
Ryan was a complete skallywag last night at the fairgrounds when he got a hold of that cocaine and he got real frisky with that horse.
by Dickcheese McGoo May 6, 2019
A scamp or rascal - a malevolent scoundrel - who is living their best pirate life in the modern world. Not bound by social norms or the limitations of society, but living life while there is living to be had.
That Skallywag caught a monster Marlin today and is celebrating its release with a good rum.
by Jack S. March 4, 2022
A member of the notorious Motorcycle Club Skallywags MCC from north west of England.
Those fucking Skallywags are always up to something.

Those Skallywags are loveable rogues.
by Sally Wagski November 21, 2020
another word for sexual intercourse, i.e fucked, boned, nailed, delivered the goods
Dogg, i totally skallywagged April yesterday, she cummed twice
by Omar Pizzle September 1, 2005
an undefined itch in the genital area caused by skeletors and is spread making new skeletors.
i had sex with that skeletor girl and woke up the next morning with a bad case of the skallywags.
by g money1 November 16, 2010