- A salesman. Immediately likable, Hickey speaks like a salesman with an "easy flow of glib, persuasive convincingness." His shrewd eyes can take in anyone at a glance, thus his immediate intuition that he and Parritt have something in common. Hickey is the saloon's anxiously-awaited guest, his arrival promising free drinks and 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 the bar, thus Hickey is the "Iceman," or Death.
in-depth analysis of Theodore Hickman.
- The play's "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 his death. O'Neill notes that Larry has a "mystic's meditative pale-blue eyes with a gleam of sharp sardonic humor in them" and his look of "tired tolerance" gives his face the quality of a weary priest.
in-depth analysis of Larry Slade.
- A gangly, awkward eighteen-year-old who has come to Larry upon a crackdown on the Anarchist movement made possible by his treason. Larry was once his Anarchist mother's lover. Wracked by guilt over his betrayal of his mother, he will beg for Larry's judgment throughout the play and progressively come to acknowledge the hate that underpinned his treason. In this sense, he serves as Hickey's double.
in-depth analysis of Don Parritt.
- 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 and his pipe dream is that he has remained inside out of respect for his dead wife Bess.
in-depth analysis of Harry Hope.
- The night bartender. Rocky is a Neopolitan-American in his late twenties, squat and muscular with a swarthy face and beady eyes. He is tough, sentimental, and good-natured. His pipe dream involves his refusal to admit to himself that he is a pimp.
- A former Anarchist editor who served ten years in prison for his activities. Hugo is a small, fastidiously clean man with an over-sized head, a "walrus mustache" and black eyes that peer from behind thick spectacles. A "foreign atmosphere" pervades him, Hugo bearing the "stamp of an alien radical, a strong resemblance to the type Anarchist as portrayed, bomb in hand, in newspaper cartoons." His pipe dream of political liberation allows him to deny his desire to rule over the masses. He is drunk for the entire play, intermittently rousing from his stupor to denounce the crowd, whine for a drink, and make odes to Babylon.
- A born grafter, con man, and practical joker. Mosher is a fat, bald in his late fifties with an unshaven kewpie's face. His erstwhile circus career manifests itself in his flashy worn clothes. His pipe dream consists of his return to the circus.
- Mosher's drinking partner. The fiftyish McGloin has the look of his former police days stamped all over him. His once brutal and greedy face has melted into a "good-humored, parasite's characterlessness." He dreams of disproving his conviction on graft charges and returning to the police force.
- A man in his thirties who left Harvard Law School upon the ruin of his prominent industrialist father. Willie dreams of starting his legal career and he speaks with "mocking suavity." Dressed in paper-thin rags, he shudders continually in his drunken stupor, his eyelids fluttering "as if any light were too strong for his eyes."
- A black man in his fifties who dreams of re-opening his colored gambling house. He wears a once-flashy suit and sports a scar across his left cheek. O'Neill notes that his "face is only mildly Negroid in type" and Joe's pipe dream involves a degree of passing as white.
- A huge Boer in his fifties whose once strapping frame has drowned in a blubbering mass of "flaccid tallow." He is Lewis's drinking partner and dreams of returning to South Africa, having left in disgrace for his cowardice during the Boer war. He is distinguished by his comic accent.
- A veteran from the Boer War, Captain Lewis is as "obviously English as Yorkshire pudding." He is in his late fifties, of a lean and erect figure, and sports a war wound on his left shoulder. He dreams of returning to England, having been driven out upon losing his regiment's money in a drunken night of gambling.
- Has the face of an "old, well-bred, gentle housedog" with guileless and bloodshot eyes. He has the manners of a gentleman, mixing the qualities of a "prim, Victorian old mad" and a boy who has never grown up. He dreams of returning to his newspaper career. As his name suggests, he is the leader of the so-called "Tomorrow Movement," endlessly deferring the realization of the pipe dream to the day after.
Pearl and Margie
- Rocky's two "tarts" are feather-brained, sentimental, lazy, and reasonably content with life. Though they retain a degree of youthful prettiness, their trade is beginning to wear on them. Their pipe dream involves the denial of their status as whores. They relate to their pipe as two affectionate sisters might with a bullying brother.
- A thick-necked, barrel-chested, swarthy, and amiable Italian American who serves as the day bartender. He shares a pipe dream with his lover and whore Cora about getting married and buying a farm in Jersey.
- A thin, peroxide blonde a few years older than Rocky's tarts whose doll-like prettiness has begun to decline.
Moran and Lieb
- The two, ordinary-looking policemen who arrest Hickey. Moran is middle-aged and Lieb in his twenties.