The film is set in Portland in 1971. Bob (Matt Dillon) is a dope addict and the head of a little gang of dope addicts that includes his wife Dianne (Kelly Lynch), Bob's buddy Rick (James LeGros), and Rick's girlfriend Nadine (19-year-old Heather Graham in her Star-Making Role). Bob specializes in robbing drugstores. Sometimes they create a distraction in which Annie fakes a seizure in the front of the pharmacy while Bob ransacks the pill drawers. Sometimes they simply climb through open windows.
Bob's little gang is closely monitored by an anti-drug unit led by a cop named Gentry (James Remar). One day Bob pulls a prank on a police surveillance team that winds up getting a cop shot. The gang decides to leave town for a while, which provides them with a chance to execute one of Bob's pet ideas, namely, robbing a hospital. Things go awry.
William S. Burroughs pops up near the end as Tom, another drug addict living in the same flophouse hotel as Bob.
- all lowercase letters: The opening titles are presented this way.
- And Starring: "And William S. Burroughs as Tom the ex-priest."
- Answer Cut: Gentry has come to the house on a raid, but his squad can't find the drugs—Dianne buried them in the backyard. Gentry says to the gang, "You can just tell us where the drugs are and save yourself a lot of trouble. Or you can sit there with your mouths shut and we tear this place apart board by board. So what's it gonna be?" Cut to the next morning, with the gang relaxing in a house that's been trashed after Gentry's squad tore it up board by board.
- The rituals of heroin addiction—cooking the heroin in a spoon, filling the syringe, injecting into a vein—are shown in extreme closeup. Later in the film after Bob gets clean, the tea he makes and the cigarettes in an ashtray are also shown in extreme closeup, underscoring that addiction takes different forms.
- Bob's Mushroom Samba involves a dreamy vision of stuff like trees and cars floating across the sky. When he's burying Nadine he seems to have an Imagine Spot of the same sort of vision, but instead of trees and cars and houses floating, it's unlucky hats.
- Call-Forward: Tom, who still uses and is very cynical about the drug war, predicts that authorities will use drug hysteria to create "an international police apparatus." That's pretty much what happened.
- Chekhov's Gunman: David, seen early in the film as the Butt-Monkey neighbor who goes to Bob looking to score some dope. He comes back at the end of the movie, having moved up a bit in the drug-pushing world, and shoots Bob.
- Cowardly Lion: Bob is pretty open about his neuroses and his reliance on drugs to keep the stresses of world away from him. The people around him are still awed by the acts of magnificent bastardry he performs out of sheer panic.
- Disposing of a Body: What's bad? Having to get rid of a body of one of your drug buddies after she overdoses in a hotel. What's worse than that? Being told that you have to vacate the room because it's reserved, while the dead body is still in the room. What's worse than that? When the room is reserved for a sheriff's convention and you have to get the dead body out of the room while the whole hotel is crawling with cops. Luckily, Bob has a garment bag.
- Drugs Are Bad: If you do drugs you may end up dead on the floor of a fleabag hotel. You might also find yourself having to bury the body of your drug companion, after you find her dead on the floor of a fleabag hotel.
- Dutch Angle: All the shots are off-vertical as Bob explains his crackpot superstition about not leaving a hat on the bed.
- The Fellowship Has Ended: Nadine dies and Bob decides to get clean, which causes Dianne to leave him. Later Dianne visits once more and tells Bob that she's Rick's woman now and Rick has his own crew.
- Five-Finger Fillet: David's buddy/fellow thug is doing this when Bob comes over to visit. This helps establish the fellow thug as David's enforcer when the two of them pop up again near the end.
- Foreshadowing: As the gang delights in finding out that part of their pharmacy score was a very valuable bottle of Dilaudid, Bob warns them to be careful with it, saying "That stuff can kill you." Sure enough, Nadine later overdoses on the Dilaudid.
- Gray Rain of Depression: The rain establishes a melancholy mood as Bob rides the bus back home, having decided he will quit the life and get clean, which necessitates breaking up with Dianne who has no interest in getting clean.
- How We Got Here: Opens with Bob being whisked to the hospital in an ambulance, as he speaks about his gang in the past tense, talking about how "we played a game you couldn't win." Then the story unfolds.
- Jitter Cam: Seen in the home movies of the gang at the beginning and the end.
- Left Hanging: Bob gets shot. The film ends with Bob being whisked to the hospital in an ambulance, reflecting that he's going to a place where he'll get all the drugs he wants. The last line is Bob's voiceover narration saying "I'm still alive. Hope they can keep me alive." Then the movie ends.
- The Loins Sleep Tonight: Bob has lost interest in sex, as all he can think about is drugs and getting high. In one scene Dianne puts a record on the record player, takes her shirt off, and tries to seduce him, and fails.Dianne: You won't fuck me and I always have to drive.
- Mushroom Samba: The euphoria of heroin is represented onscreen with a dreamlike sequence in which things like cars, houses, and trees float across the sky as a gentle soundtrack plays.
- Poke in the Third Eye: Bob knows the cops are watching him. So he sends in a fake tip to Gentry to the effect that Bob gets his drugs via a string hung between his apartment and the neighbor's across the street. Bob then tells his neighbor that he saw somebody peeping in on the neighbor's daughter. This backfires to a certain extent when the neighbor comes out with a shotgun and shoots the cop.
- Punk in the Trunk: The fate of poor Nadine, dumped in the trunk of Bob's car and eventually buried in the woods after she overdoses in the hotel room.
- Retirony: Bob gets straight and gets his life together—he even has a paying job!—only to get shot and possibly killed by David, who is looking for Bob's stash.
- Tempting Fate: Nadine, who is in a bad mood, ridicules Bob's superstition about a hat on the bed. As the rest of the gang goes off to rob the hospital, she deliberately puts a hat on the bed to prove that Bob's superstition is nonsense. The raid on the hospital turns out to be a fiasco in which Bob barely avoids getting arrested, and then the others come home to find Nadine dead of an overdose.
- Tropaholics Anonymous: Despite being extremely cynical about addiction treatments, Bob goes to sessions.
- We Need a Distraction: One of the gang's stock operations, in which Nadine pretends to have an epileptic fit, allowing Bob to jump behind the counter and steal pills while the pharmacist is out front.
- Your Television Hates You: Bob is telling the story of why he won't allow anyone to even talk about dogs—he and Dianne once had a pet dog, and their faithful dog led the cops to their house. As he finishes, the television starts showing dog commercials on every channel.