A new assistant to a powerful executive wants more than just to do a good job, she wants to run the company! And she'll do anything to get to the top, even murder.

After he accidentally kills his father Mike during a sting, Joe tries to carry out Mike's dying wish by recovering valuables that Mike's twin brother Lou stole from him years earlier. But Uncle Lou is also a confidence artist, and Joe is soon drawn into his increasingly dangerous schemes.

Tony Lip, a bouncer in 1962, is hired to drive pianist Don Shirley on a tour through the Deep South in the days when African Americans, forced to find alternate accommodations and services due to segregation laws below the Mason-Dixon Line, relied on a guide called The Negro Motorist Green Book.