Billy, Patrick Dempsey, is a bank robber who dresses sharp and arrives at the bank with a dozen red roses, declaring one last heist so he can sail off to a tropical island with his girlfriend Selina, Olivia d'Abo. The couple’s plan unfolds against a backdrop of mounting tension and mounting fantasy, as Billy envisions a carefree future with Selina while the real world throws him a series of escalating obstacles.
On this final job, Billy shoots out all but one of the surveillance cameras and then must hide out in the Heartbreak Hotel until the heat dies down. As the city watches and a televised news report broadcasts his face and alias — William James Elliot, a.k.a. Billy the Kid — everyone he knows starts circling for a share: hotel clerks, pizza delivery people, and even routine workers recognize him and his predicament. In the meantime, back at the bank, the police chief and the bank manager use the distraction to crack open the vault and pass out the money, even though Billy only targeted tellers’ cash. The manager daydreams about a BMW while the police chief imagines an RV as his next purchase, painting a surprisingly ordinary picture of ordinary desires amid the crime that drew the spotlight.
Billy attempts to reach Selina, but the moment is brief — agents are listening in. As Billy slips deeper into paranoia, Selina herself becomes entangled in a troubling contradiction: she is shown having sex with Billy’s friend Chris, James Garde, while Billy clings to a dream of escape. The financial fallout follows close behind: Billy faces charges for things he didn’t order, and the bank announces that nearly $200,000 is missing — ten times what he actually took. In a strange turn of business-as-usual, Priscilla arrives, an escort service figure who initially jobs for a price but ends up staying, weaving a new dynamic into Billy’s precarious loneliness.
Two beat cops wander the streets, quietly wrestling with the question of Billy’s background and what his upbringing may have to do with the life he’s chosen. In a dream sequence, Billy envisions visiting Selina again, only to hear a news broadcast proclaim that the robber confessed. The fantasy intensifies as the couple buys a red Mustang convertible and head toward a waiting sailboat, chasing the image of a paradise that remains stubbornly out of reach.
When Billy awakens to a knock at the door, a TV personality and her crew intrude, and Billy’s face is shown in full. A clip of Selina appears, claiming she loves him, but she’s after a quiet, ordinary life. The broadcast sums up a cruel judgment: he must be retarded. The mood shifts again as Billy grows more paranoid and builds a model of the beach he longs to inhabit, while Priscilla visits and they share a meal and more intimacy. His mind drifts into another round of dreams: a gay cop tries something with him, then Selina reappears on the beach, morphing into Priscilla in his dreamscape.
Reality bleeds into the surreal as Billy begins to dismantle a leftover pizza, rearranging its ingredients in feverish little rituals. He eventually dresses, leaves the motel, and encounters the two beat cops on the street — they shoot him and carry him away to Priscilla. She pays them and drives off with a wounded Billy. Sometime later, Priscilla is seen on a beach with Billy, watching the sunset, a final image that lingers on the line between fantasy and a troubled, stubborn reality.
