FREE: Duane Hopwood David Schwimmer, Janeane Garrofolo, Judah Freidlander Brand New Sealed DVD

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The film opens with a montage showing Duane's slide into alcoholism: starting with a happy family meal; moving onto a scene of him drinking casually at home; then a scene of him drinking in a bar after work; then coming home drunk, leaving the car with the door wide open and half on the curb while he is crashed out on the bed—still in his work clothes from his overnight shift as a floor manager or "pit boss" at Caesars Palace casino in Atlantic City, New Jersey. The montage culminates when Duane is pulled over after continually swerving across the road. Duane is drunk, but the policeman, a close friend, offers to take him home. Duane agrees but his friend's leniency changes after Duane tells him his daughter is in the back seat.

Duane is banned from driving and is forced to travel to the casino by a bicycle borrowed from his ex-wife Linda. Luckily, Duane's colleague, Anthony (Judah Friedlander), sees him and offers him a ride. At the casino Duane is forced to intervene in an altercation between a blackjack table dealer and a customer. Duane initially asks him to leave, but after the man asks for a second chance, Duane gives him a few quarters and asks him to play a few slots then leave. The man does so and wins the jackpot prize.

Duane meets his ex-wife Linda at the pier and she tells him that his oldest daughter, Mary, would like to talk to him and also informs him that her lawyer has suggested she revoke his visitation rights because of his DUI. In anger he chucks the bicycle into the sea.

Needing to call a cab, Duane returns to the casino, but gets asked to take a walk by his boss. Duane is taken into his boss's office to explain his part in a dispute between the slot machine winner and an old lady who says that it was "her machine". Duane confirms, falsely, that it was the man's own quarter which was used to win the jackpot. Duane's boss explains that the dispute is a "potential public relations nightmare".