War has- regrettably- been the answer to many conflicts in human history, ranging from the Sumerian’s conquests to the invasion of Iraq by the US and its allies. During its long history, war has been questioned and contemplated, especially through culture: music, poetry, literature, etc. Two prominent pieces of anti-war literature include Catch-22 by Joseph Heller and For Whom The Bell Tolls by Ernest Hemingway. Both novels express contemporary fears and questions on war: its impact, its conduct, and its purpose; as well as frustrations and dangers of a modernizing society, industry, and bureaucracy, however the former has a comedic tone, while the latter is serious. Tone is a very powerful and moving tool for both Heller and Hemingway in their novels. In Catch-22, comedy through absurdity is the overwhelming tone. Heller uses the comedic tone to explain that “[w]ar is irrational”, and leave the reader with a “catharsis in which the grimness of war provides the dominant memory”. Heller does so by creating absurd situations that may begin as funny, however leave one with a “bitter pessimism” (Hasley). An example of this is the tale of Captain Half-Oat, whose family had been Native Americans who, whenever they settled, would happen to settle directly over an oil deposit and be evicted by oil companies. This happens several times, and while Native American oppression is obviously a dark topic, it is presented in a humorous tone. However, when the reader contemplates the deeper