This chapter focuses on Roberto Bolaño poetical imagination; not only his poetry, but the way he uses poetry and the poet, as a literary figure, to stage an ironic and parodic representation of literature in the context of ongoing globalization. My main contention is that the exilic condition of Bolaño’s life and works defines his relationship to Latin American literature at large; thus, far from repeating conventional investments in literature’s potential to express Latin American singularity and to, somehow, supplement the historical process as a process leading to final liberation, what predominates in his works, and particularly in his decisive novel The Savage Detectives, is a skeptical understanding of the final disarticulation between literature and history. His characters, in other words, far from the mythical investment of Latin American romantic and revolutionary-like characters of the past, are defined by a nomadic and uncertain way of living detached from the age of commitment and political programs.