Welcome to the saddest bar in the whole wide world. It’s the summer of 1912, and as life breezes by just outside the smeared windows of Harry Hope’s saloon and boarding house, things are pretty dismal inside. The place looks like the world’s most depressing birthday party or a Jersey Shorereunion.
Regular patrons and boarders sleep off their hangovers during the day as Rocky Pioggi, the nighttime bartender, sets up for the evening. Larry Slade, a 60-year-old former anarchist who swears he’s done with the Cause and pretty much done with life, tells Rocky he’ll pay off his bar and room tabs “tomorrow.” As the other men in the joint start to wake up, they claim the same thing. They all kind of laugh when they say it, though, so it’s a good bet nobody plans on paying anybody for anything anytime soon.
Once they’re all awake, the group gets fired up about the impending annual arrival of Theodore “Hickey” Hickman. They know when Hickey arrives he’ll buy them all the best booze and brighten up everything in the bar. They’re a bit thrown off, though, when a teenaged stranger named Don Parritt arrives. See, people in Harry’s don’t take too kindly to strangers. Slowly, Parritt reveals that he’s the son of the single mother that Larry once loved. Parritt has come to Larry for help. His mother, one of the leaders of the Cause, got sold out by a fellow member and has ended up in jail.
Before the plot can get too much like an episode of Secret Life, Hickey finally bursts onto the scene like the rock star he is, but the group quickly discovers Hickey is a changed man. He calls out everyone who lives their lives based on pipe dreams and talk of “tomorrow.” Soon, they all start to resent Hickey. The only one who seems unimpressed by Hickey’s life change is Larry. Larry presses Hickey on what happened to cause this change. It turns out that Hickey’s wife has died under somewhat strange circumstances. Though Hickey won’t tell him more, Larry believes Hickey’s wife killed herself.
As Hickey presses his agenda, the regulars turn on him and on each other. This bar really is like a Jersey Shore reunion, though with less hair product and more old men. In the morning, one-by-one, the regulars hand over their room keys and head out the door. They’re finally going to start walking the walk.
Eventually, they all come back without having followed through, though. But, it turns out that this is what Hickey had planned all along. He wants them to realize that once they give up their pipe dreams they can be truly in the moment and therefore truly happy. Not surprisingly, the others don’t react well to realizing that their dreams had been used against them. Nothing seems right anymore. Even the alcohol stops working.
Larry wants Hickey to admit his wife killed herself. Instead, Hickey confesses he killed his wife and turns himself in to the cops. That leads Parritt to confess he sold his own mother out because he hated her. To deal with his guilt, Parritt throws himself off the fire escape. No one other than Larry even notices, because they’re celebrating. Crazy dark endings are O’Neill’s specialty.
Other than Larry, everybody thinks Hickey was crazy all along and they claim that everything they did—leaving the bar and pursuing their pipe dreams—was just to humor him. The drinks taste great again. They’re getting drunk again. They’ll start following their dreams tomorrow. They even claim to love Hickey again as the police drag him away. Only Larry realizes what has really happened. He recognizes that Hickey wasn’t crazy, and that life is pretty much a deep, dark pit of despair with only one depressing way out.