“Somewhere a colored woman was singing a mournful dirge about ‘That Bad Stackalee.’ The verses were endless. The point of the song seemed to be that the negro bully, Stackalee, had been killed with ‘a big forty-four gun over a damned old Stetson hat.’ In the most harrowing tones at the end of every verse the singer moaned the sad refrain, ‘That Ba-ad Stackalee.’

“Later I came to know that this song is a favorite among negroes when in great trouble, such as being locked in jail, being double-crossed by a friend, or parting with money in a dice game. At such times thirty or forty verses of ‘Stackalee’ invariably restores the laughing good humor and child-like confidence of the wronged one.”

-Jack Black, from the 1927 book You Can’t Win

Modern academics will dismiss this passage as racial slander, having never known the “childlike confidence” of postmodern urban African American criminals as have this researcher and many another white trash person who has been wrongly mistaken as a middle class white bread cuckold by urban youth bounding gleefully to the task of doing him in, only to scatter in jabbering consternation when the target of their crime turns out to be “the wrong white man,” as I was once declared to be on the parking lot of a Baltimore County pizzeria by the chieftain of the bantu warrior who had been sent over to relieve me of my dignity only to retreat at the point of my green umbrella.

Stackalee, from the context of the song, was a man of color making his way among free men until, like “Bad, Bad Leroy Brown” from the rock and roll song, he came up against a man armed with a gun. This is of importance as free men of African descent and free European American men recently escaped or released from bondage, had lived for some 250 years in a world patrolled by soul traders, gaolers and slave catchers and inhabited by armed and independent men. In such a world the runaway, freedman or freeman who was not armed would soon discover that his freedom was not a right but a privilege tolerated by men with the ability to take it and his very life at the point of a gun. The disarmed POWs from Ireland, Scotland, England and Africa, and the kidnapped and disarmed civilians of the British Isles seem to have entered and exited American bondage with a keen sense of gun culture tied to their prospects of liberty. American gun culture from the earliest times is rooted in bondage at the point of a gun. This has had and continues to have predictably dramatic ramifications for disagreements between criminals, a famous aspect of Americana that stems from its unfree origins. In the late 1800s when the events that inspired the song occurred, it was very common for men of all races in America to be enslaved in prison work programs, as the 14th Amendment guaranteed that legal fraud would be used to access free labor for the privileged classes.

Frank Hutchison (1927) - Stackalee

Loyd Price (1959) - Stagger Lee

STAGGER LEE (1969) by Taj Mahal