The saloon's great "Foolosopher," Larry is a tall, raw-boned Irishman in his sixties who was once a Syndicalist-Anarchist. Having bitterly retired from the world, he presents himself as a man who has chosen to watch the carnage from the grandstand of philosophical detachment and eagerly awaits the end. This supposed withdrawal from the world is precisely his pipe dream, his pose of philosophical detachment concealing his fear of death and desperate hold on life. Parritt's demands that he pass judgment on his crimes will force his engagement with the world anew, an engagement that only increases his yearning for oblivion. Larry is the play's ironist, commenting sardonically on the group's tomorrow dreams and the deadly cruelty in the peace Hickey offers. Balking at this pose of detachment, Hickey will accuse Larry of suffering from a dangerous sense of pity. Indeed, as Willie notes, Larry is the kindest among the residents of Harry Hope's saloon, readily colluding in their pipe dreams to alleviate their suffering. Larry's functions appear inscribed on his face. As O'Neill notes, he has a "mystic's meditative pale-blue eyes with a gleam of sharp humor in them"; his look of "tired tolerance" gives his face the quality of a weary priest.
Hickey is the saloon's anxiously awaited guest. Immediately likable, Hickey speaks like a salesman with an "easy flow of glib, persuasive convincingness" and always promises merriment. However, this time the group's messiah, so to speak, comes bearing a different gospel of salvation, urging them to divest themselves of their pipe dreams and finally make peace with themselves. Hickey's murder of the tomorrow dreams will bring ruin to the bar, thus Hickey's advent is the advent of the "Iceman" or Death.
As Larry notes, Hickey has also brought death to his own house, murdering his wife. We learn of this murder in the course of Hickey's doubling with Parritt. In the stage directions, O'Neill indicates that Hickey's shrewd eyes can take in anyone at a glance, and his immediate intuition is that he and Parritt have something in common. They double each other in their ambivalent, love/hate relationships with their love objects, in Parritt's case, his mother, in Hickey's, and his wife Evelyn. For both, the hatred they cannot admit to themselves manifests itself quite violently, impelling Parritt to betray his Anarchist mother to the police and Hickey to murder his wife.
Upon his confession this murder, Hickey's gospel of salvation will reveal itself as its own pipe dream, a delusion that allows him to elude his guilt over his crime. By killing his wife, he imagines that he has freed them both from her pipe dream of his ultimate reformation as a drunken adulterer. Thus Hickey has come to insist on the murder of the pipe dream as the path to salvation. The hate that motivates this killing, a revenge for driving Hickey mad with guilt, will only make itself known to Hickey in his final scene. As with the others, the demystification of his pipe dream will then lead him to relinquish life. Thus he delivers himself to the authorities and begs for his execution.
Parritt is a gangly, awkward eighteen-year-old. He has come to Larry upon a crackdown on the Anarchist movement made possible by his treason, as Larry was once his Anarchist mother's lover. Though good-looking, Parritt has an unpleasant personality, showing a "shifting defiance and ingratiation" in his eyes and an "irritating aggressiveness" in his manner. Parritt's development involves the progressive confession of his betrayal and its motivating force, a long-nursed hate for his mother. In bearing a hate inadmissible to his conscious, he serves as Hickey's double.
Certainly Parritt hates his mother for her commitment to the Movement at the expense of himself. As he frequently sneers, she probably thought she was the Movement, making his betrayal of the conspirators a crime against her. Much of this hatred also appears to lie in his fantasy of mother as whore—as he tells Larry, life with such a "free woman" made his childhood home a brothel. Such anxiety over the woman as whore appears throughout the play. Larry leaves Parritt's mother, for example, because of her promiscuity; Pearl and Margie are sensitive to the epithet. It is easy to postulate an Oedipal desire behind Parritt's spite, the mother who potentially belongs to others becoming, in the eyes of the envious son, a debauched prostitute.
Wracked by guilt over his betrayal of his mother, he will beg for Larry's judgment throughout the play. The demystification of his delusions about his hate leads him to a necessary death. Within the Last Supper tableau of Harry Hope's birthday party, Parritt thus appears as a Judas-figure. Like Judas, he will suicidally submit to a death sentence as his punishment.
The owner of the saloon, Harry is a "bag of bones" in his sixties with the face of an old, balky family horse. He wears spectacles so misaligned that at times one eye peers over one lens while another looks half under the other glass. Likable to all, he hides his vulnerability behind a "testy truculent manner" but fools no one. Hope has not ventured outside the bar in twenty years. His pipe dream is that he has remained inside out of respect for his dead wife Bess.
The demystification of his pipe dream forces him to confront the reality of his desires: his hate for Bess and his fear of the world outside. This demystification condemns him to a sort of living death. As he remarks upon returning from his abortive venture into the neighborhood, it leaves him feeling like a corpse. If Harry's flights of fancy seemed, like those of the others, vaguely mechanical, their demise truly makes him into an automaton attempting to benumb himself to the world. Harry's fall prefigures the analogous metamorphosis of the saloon's residents upon the ruin of their pipe dreams. Similarly does his revival of his delusions, what he aptly describes as a second birthday, lead the group in their return to their own.