The main purpose of this study is to show the nature of Shakespeare’s comedies and their stages of development from light comedy to intellectual comedy, and finally to gloomy comedies that border on tragicomedy. Although Shakespeare’s comedies are, as a whole, different from those of his contemporaries and classical playwrights, they do not follow a certain pattern. Shakespeare sometimes chooses the tradition and conventions of classical comedy and manipulates them in his own way, but very often he neglects the traditional conventions and writes a different kind of comedy. Shakespeare’s comedies are in many ways different from those of Jonson and other followers of classical comedy. His comedies are not satirical and they don’t arouse hearty laughter. The characters in his comedies make us smile, but they do not evoke cruel laughter. This study endeavours to explore the difference between Shakespearean comedy and classical comedy, and Shakespeare’s deviation from those conventions is mentioned with references to some representative comedies. What makes his comedies Shakespearean is the fundamental argument of the present study.