Cadillac Man 1990

As the clock ticks down on Joey O’Brien’s two-day ultimatum to sell twelve cars or face losing his position at a Queens car dealership, the mounting pressures in his life reach a peak. His estranged ex-wife, Pamela Reed, relentlessly pursues him for alimony, while his daughter remains missing, adding to the anxiety. On top of that, Joey finds himself tangled in romantic liaisons with not one, but two mistresses, which are teetering on the brink of chaos. To complicate matters further, he grapples with a looming loan from a menacing Mafia don, creating a cloud of dread that hangs precariously over him.

When the dealership hosts a significant car sale, the situation escalates dramatically as Larry, a vigilant motorcycle rider brandishing an AK-47, seizes control of the premises. Driven by wild suspicions of infidelity, Larry demands answers from Tim Robbins, who portrays Joey O’Brien. As law enforcement cordons off the dealership in response, Joey sees a moment to alleviate the tension through negotiation, fabricating a story that he has been having an affair with Larry’s spouse.

In an unexpected development, a bond forms between hostage-taker and negotiator, leading Joey to persuade Larry to surrender without incident. However, unbeknownst to them, this crisis is merely the tipping point of further chaos. The stakes skyrocket when police mistakenly shoot Larry after most hostages are freed. Joey remains steadfastly by his side during recovery, confronting a shocking revelation: he never actually had any romantic involvement with Larry’s wife.

As the tumult subsides, the aftermath transforms Joey’s life in astonishing ways. His two mistresses discover each other, resulting in their immediate departure from his life. Interestingly, Joey’s daughter returns home, securing his job status, and the Mafia don—whose son was among the hostages—graciously forgives Joey’s debt. Amid this whirlwind, he begins to mend his fractured relationship with his ex-wife, painting a complex portrait of redemption and unexpected shifts in fortune.