The Iceman Cometh shares a number of aspects with the tragedies of old, but it shouldn’t be seen as a shining example of the form. One reason for this is that there isn’t a clear-cut hero in O’Neill’s play. Larry could be thought of as something like the protagonist, but he’s pretty inactive throughout most of the play. Hickey, on the other hand, clearly has the whole "falling from grace" thing that’s common among tragic heroes, but his story really takes place off-stage, before the action even begins, and the play functions more like a revelation of his tragedy, rather than a dramatization of it. Still, he’s our best bet as tragic hero.
The play truly opens with some anticipation—namely of the arrival of Hickey. But that’s not the only anticipation towards the beginning of the play. Hickey, as our anointed tragic hero, anticipates saving his friends from their forsaken pipe-dreams. He explains to them how he’s going to set them free, saying, “But I didn’t mean booze. I meant save you from pipe dreams” (1). Hickey’s convinced he’s going to help them find peace, and he just knows they’ll be grateful to him once he does.
This stage takes place towards the end of Act II and the beginning of Act III when it actually looks like the denizens of Harry’s bar are making changes in their lives. Cora and Chuck go off to get married, Willie quits drinking, Jimmy Tomorrow gets off his butt. The crowning achievement, it looks like, is when Hickey manages to get old Harry to set foot outside the bar and embark on his twenty-years-in-the-making saunter around the old hood. Not everything is all peachy though, as everyone is kinda resentful towards Hickey and each other. But those pipe dreams are being put to the test…
Spoiler alert: folks aren’t actually successful in achieving their pipe dreams. Cora and Chuck never even make it to New Jersey, and Harry’s attempt to cross the street was cut short by an imaginary automobile. But rubbing it in like this was Hickey’s plan all along. As he tells Harry, “You’re rid of all that nagging dream stuff now. You know you can’t believe it anymore” (3). So frustration is definitely widespread at this stage, but not only for Harry and the others. Hickey’s frustrated too—he thought people would be grateful that he had disabused them of their pipe dreams. But the exact opposite has happened. Frustrated, he tells Harry, “it’s time you began to feel happy” (4).
The nightmare really comes alive when Hickey launches into his horrific tale of how he killed his wife. Everyone is so depressed about their pipe dreams being ruined that they don’t even key into this heartbreaking tale and just jeer him on to shut up already.
Things are all over for Hickey. Unbeknownst to the others, he’s turned himself in and the cops are there to cart him off. Remarkably, this ends up turning the group around, but not in the way Hickey imagined. They think he’s been crazy all along and convince themselves that they just went along with him to help him out. Now, they can go back to living their lives like they did before, pipe dreams and all. Hickey will end up on the electric chair in all likelihood. But that’s not his only downfall at the end of the play. His whole plan of turning his friends around and setting them on a path that’s not so free of self-deception has failed. What’s worse, his conduct has convinced them that he was crazy and they can all go on in their benighted self-deceived ways.