Other spellings for Stackolee, the name of the notorious black folk bandit abound: Stagolee, Stackerlee, Stackalee, and Stagger Lee have all been collected. The first references to the outlaw emerged in the 1890s. It is important to note, however, that collections of folklore from African Americans were virtually nonexistent before that time, so this tradition may be much older than the evidence suggests.
Stackolee is prominent in folk literature, namely songs, toasts, and folktales. Many of these genres focus on the deeds of thoroughly “bad men.” Stackolee is probably the most well-known of these characters. Because he has lost his beloved Stetson hat while gambling, Stackolee engages a hard-living black man Billy (or Bully) Lyons (or Lion) in a gun battle. Citing family considerations, Billy eventually begs for mercy, but Stackolee shows no sympathy. In most versions, Stackolee's reputation for evil is so powerful that law enforcement officials fear him; sheriffs and deputies refuse to pursue him. In some versions, the judge refuses to send Stackolee to jail because he fears the bandit will somehow seek retribution. In others, Stackolee responds to a ninety-nine year sentence by boasting, “Judge, ninety-nine ain't no goddamn time / My father's in Sing Sing doing two ninety-nine.” In other versions, the hangman refuses to execute him, or his neck won't snap after the noose has been tightened. Folklorists have argued that Stackolee and other bad black men in folk tradition owe their appeal to the African American public's awe for men who disdain all conventions. So long victimized by the institution of slavery and the second-class citizenship that followed, many African Americans developed a fondness for stories about men who disdain all conventions.
Lawrence Levine, Black Culture and Black Consciousness: Afro-American Folk Thought from Slavery to Freedom, 1977.Cecil Brown, Stagolee Shot Billy (2003).
—Patricia A. Turner