The Iceman Cometh is set on a summer day of 1912 in Harry Hope's saloon. The patrons of the saloon are all drunkards and prostitutes. In the first act of the play we are introduced to the characters, who bicker among each other and ramble about their past, dreams and plans for the future. Among the various characters we have Pat McGloin, a former police lieutenant kicked out from the force on criminal charges, Joe Mott, an African American who used to own a casino, Hugo Kalmar, a former anarchist, Captain Cecil Lewis, a former British Infantry Captain, Larry Slade, a former anarchist, James Cameron, who fought in the Boer war, Pearl and Maggie, two prostitutes. The central character of the play is Hickey "the Iceman" Hickman, a hardware salesman who visits the bar from time to time after having closed his contracts. He becomes the life of the party, buying drinks for everybody and entertaining the crowd with his stories.

Willie Oban, the character delivering the monologue, is a haggard, drunk former Harvard student, son of a wealthy businessman who lost his fortune. In this monologue, just after waking up and before begging for another drink of whiskey, Willie rambles about his time at Harvard and how his father made his money and then lost it.