The Old Settler is the story of two middle-aged sisters, Elizabeth and Quilly, who share an apartment in Harlem in 1943. The sisters quarrel amiably, but they share a wounded history that becomes revealed as the tale unfolds. An earnest but unworldly young man named Husband travels up from the South to board with the sisters while he searches for his beloved Lou Bessie, who left their small town a few years back to find a new life. Husband would like to bring Lou Bessie back home, but she's enamored with the excitement of the city, and her plans are more complicated. In time, Elizabeth and Husband begin a courtship that may or may not overcome their considerable age difference, while Quilly reacts disapprovingly.

When Butch, Postmaster P, and Stray Bullet loot the local hip-hop mogul's studio to fund their demo album, the threesome unwittingly ends up with the secret of Mack Daddy's success: a magical flute. Their gigs instantly turn golden but a blood-thristy Leprechaun and an angry Mack Daddy are hot on their trail, leaving a wake of destruction tainted by politically incorrect limericks.

Although Jo Jo Dancer has achieved success as a stand-up comedian, he hasn't found happiness. After receiving severe burns in a narcotics-related incident, Jo Jo remains in a coma, and, while in this state, he looks back on his life. Drifting off into memories of his troubled childhood, Jo Jo revisits his youth, recalling his eventual rise to fame and the decadence that followed. As he considers his existence, he must decide if he wants to go on living or not.