This research presents Woody Allen’s development from his early comedian background until late 1970’s, when he co-wrote, directed and starred two of his most iconic films set in New York City: Annie Hall (1977) and Manhattan (1979). The first part introduces his origins, the influence of stand-up comedy in the development of his comic style and his film persona, as well as the beginning of his career as filmmaker. In the second part, these two films are analysed from the perspective of building a more elaborate cinematic narrative that deals with issues of contemporary life, as well as Allen’s portrayal of New York.