Olive is a con-artist who will do anything for her 10 year old son, Bobby, but giving him the best life with no money coming in isn’t easy. Reminiscent of a modern day Bonnie & Clyde, the unstoppable pair spend their lives scamming the rich and the down right gullible, often finding themselves on the run from the law. In an effort to escape Olive’s criminal past, they arrive in Oklahoma with hopes of building a better life. Olive and Bobby blithely charm their way from one adventure to another until Olive’s finally catches up with her once and for all. Now she must make the most difficult choice of her life: stay with her son and run the risk of turning him into a criminal or leave him to afford him better opportunities? In the vein of Thelma & Louise, Bringing Up Bobby is a fast-paced crime story with the most heart-wrenching of decisions at its heart.