Examines the tumultuous life of legendary Chicago pimp Iceberg Slim (1918-1992) and how he reinvented himself from pimp to author of 7 groundbreaking books. These books were the birth of Street Lit and explored the world of the ghetto in gritty and poetic detail and have made him a cultural icon. Interviews with Iceberg Slim, Chris Rock, Henry Rollins, Ice-T, Snoop Dogg, and Quincy Jones.

Set in the 1890's, tells the lesbian love affair between male impersonator music hall star Kitty Butler and Nan Astley.