Love, resentment and a tormented intimate, in which shadows and lights hover, place the poets Dante Alighieri, Carlos Drummond de Andrade and Eugenio Montale crowned by the same threshold, that is, as if at some point they were in the same place, under the same doorway. This book aims to present a literary analysis that looks for the shadow of Dantesque melancholic poetry in some of Drummond and Montale's verses. In order to do so, the aim is initially to construct a brief literary journey and a historical overview of the bibliography of these poets, to investigate the points in common in the construction of these works and, subsequently, to map and make a connection between these works through a specific line - melancholy, a theme that will be defined throughout the text. By choosing some approximations and studying the commonalities in the texts of these poets, whether in the similarities in the construction of the characters, in the textual evolution or in the re-reading of Dante Alighieri's Divine Comedy, the intention is to highlight the relevance of melancholy in the creative force of the authors, whose shadow is the Dantesque connection.