In their theory of class formation and social revolution, Karl Marx and Frederick Engels were scathing about the lumpenproletariat, condemning it as anti-revolutionary, morally bankrupt, and a bribable tool of the bourgeoisie, a view that remained influential well into the mid-twentieth century. Not until Frantz Fanon appropriated the term lumpenproletariat in The Wretched of the Earth (1961) and applied it to what he saw as a whole class of people waiting to be brought into and redeployed as the vanguard of a new revolutionary proletarian consciousness did it shed its negative connotations. The changed trajectories of the proper place and role of the lumpenproletariat can be seen in working-class literatures of the late twentieth and twenty-first centuries, which constitute an important stage upon which to refine Marxian and Fanonian understandings of the lumpenproletariat. This essay examines three novels written in the last thirty years: Herbert, by Nabarun Bhattacharya, written originally in Bengali and published in 1993; How Late It Was, How Late, by Scottish writer James Kelman (1994); and Sacred Games, by Vikram Chandra (2006). Read contrapuntally, these works provide a literary platform for the exploration of the representational shift in the role and function of the lumpenproletariat in the twenty-first century.