This paper seeks to summarise the interplay between utopian and dystopian thinking throughout the twentieth century with a particular focus on the city. The gradually shrinking appeal of the socialist utopia and its replacement with the globalised free–market as a ‘revanchist utopia’ left socialist utopian thinking in a state of disarray towards the end of the previous century. Utopian thinking, both as a literary and political genre has been rendered marginal in contemporary political practices. Urban dystopia, or ‘Stadtschmerz’, is now prevalent in critical Western thinking about city and society. It is concluded that the declining political impact of critical urban research is caused partly by its lack of engagement with crafting imaginative alternative futures for the city. The works by Sennett, Sandercock and the Situationists, among others, may contain elements to reverse the current utopian malaise in urban research.