This comparative study explores how Aziz Nesin and Neil Simon, representing different literary canons, treat and reflect upon the incorporation of loneliness and humour in Hadi Öldürsene Canikom! [Let’s Kill Me Honey!] (1970) and The Odd Couple (1965), respectively. Both playwrights examine the loneliness that has caught urbanised and atomised humans in two metropolises: Istanbul and New York. Simon deals with the values, concerns, lifestyles, aspirations and problems of middle-class people in his plays with domestic realism. In contrast, Nesin’s plays explore lower-working-class people’s values, concerns and struggles. Moreover, it focuses on how Nesin and Simon employ humour, as a Lingua Franca of comedy, in their works. The study emphasises the two playwrights’ incorporation of the humour theories of superiority, incongruity and relief into the selected dramatic texts. The interactions between the characters in the two plays are analysed according to the three traditional humour theories by assuming a discourse-analytic approach. The study has exhibited that in Hadi Öldürsene Canikom, all the humour theories have been explicitly observed. The humour largely stems from a case of mistaken identity, which creates incongruity. On the other hand, in The Odd Couple, humour is primarily evoked due to the incongruous characteristics of the roommates abandoned by their wives.