It looked as if a tornado had passed through the house, picked up the remnants of Arrow Brown’s strange, sordid life, and dumped them in the alley.

Brown’s outsize lifestyle matched his outsize character. He was rarely without his signature cigar, .38 special, and black homburg–a rogue image that even served as Bandit’s logo for a time. Among his other accessories was a wood-handled ice pick, which he would idly pull out and hurl at some target–a tree stump, a can. A simple backwoods boy to start, a migrant to Chicago from the small-town south, Brown saw in the big city all the things he was not–sharp, tough, powerful, glamorous–but wanted to become. With a silver tongue and an iron will, he carved a life for himself of little work and lots of pleasure. To some he was a predator, to others a protector. To many he was both.

It’s a measure of the mystery Arrow Brown shrouded himself in that even his funeral program hedges about the city of his birth. What is known is that Brown was born on September 10, 1923, most likely in Merigold, Mississippi. A tiny, predominantly African-American community in the northwest part of the state just off Highway 61, Merigold is best known as a stomping ground for Delta blues legend Charlie Patton, whose 1927 tune “Tom Rushen Blues” name checked a number of local characters.

Brown soon learned to brawl and whore with the best of them. Although not handsome in the classical sense, he had a languid smile, bedroom eyes, and an unerring instinct for the slightest hint of invitation or weakness. He was a chameleon as well: he could act like a refined gentleman, a streetwise tough, or anything else the situation, or the lady, called for.

By the late 50s Brown had settled into the graystone at 4114 S. Park Boulevard (later renamed Martin Luther King Drive), which was apparently owned by his stepfather, Asabee Whitehead. Sometime around 1962 Brown befriended Johnny Davis and his young sister Mary Ann. They were introduced to him by their grandmother, whom according to family lore he’d saved from a violent attack outside a hotel. Johnny was a street-corner doo-wop singer, blessed with an elastic voice that could manage both the heights of Curtis Mayfield’s falsetto and the grittiness of Bobby Womack’s tenor. Bonding over music, he and Arrow became fast friends and running buddies. “They were like two peas in a pod,” says Mary Ann, who at age ten was entrusted to Brown by her alcoholic mother. Three years later she had the first of their three sons, Altyrone Deno.

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As the decade wore on, Brown–still working at the soup factory–kept searching for a chance to harness his talents in a way that would yield big dividends. One tempting prospect was the independent record business.

The growth of such labels accelerated over the next two decades, abetted by the exponential increase in the city’s African-American population–from 8.2 percent to 22.9 percent–that came with the Great Migration. Seemingly anyone with a song and a band could be in business. “That was the beauty of the independent labels,” says Pruter. “All you needed was a few hundred dollars to record some tracks in the studio, press up 500 or 1,000 copies, and hope that lightning struck.”