Apesar de sempre terem tido um relacionamento complicado, a descoberta de um câncer faz com que um poeta resolva se reconciliar com seu pai. Porém para isso, ele precisará enfrentar memórias conflitantes que viajam entre os anos 50, 60 e o fim dos anos 80.
Piccadilly Cowboy is about a Montana Cowboy, named Carson Wells. Carson is unmarried and living abroad in London. A fish out of water, Carson works for a high power beef company, and is dating a beautiful, British girl named Lucy. Everything seems to be going well for him in the Big Smoke. When he decides to settle for their relationship and ask Lucy's grandfather, Mr. Armstrong, for her hand in marriage, the reply is that he must first find a husband for her older sister, Gemma. Whilst finding her a potential mate, his life changes forever as he discovers true love and resolves issues in his own personal life.