By Hook or by Crook chronicles the tale of two unlikely friends who commit petty crimes as they search for a path to understanding themselves and the outside world. Silas Howard plays Shy (a transgender man), who leaves his small town after the death of his father, and heads to the big city to live a life of crime. Along the way, he encounters Valentine, a quirky adoptee, in search of his birth mother. An immediate kinship is sparked between these men and they become partners in crime. Suffering money troubles, emotional problems, and physical confrontations, the duo face their issues head on and learn to trust each other and support each other in pursuit of their goals.