Two men reaching middle age with not much to show but disappointment, embark on a week long road trip through California's wine country, just as one is about to take a trip down the aisle.
Miles is a failed writer living a meager existence in San Diego as an English teacher. With his career seemingly fading and the fate of a book hinging on a publisher's decision, Miles is depressed with himself and what he hasn't achieved. Jack is a television actor whom some recognize but not many do, as if he were a minor actor who got a taste of success. With his best friend Miles, the two embark on a road trip through California's wine country. Miles wants to give his friend a nice sendoff before married life, while Jack simply wants to have a fling beforehand. As they're both nearing middle age with not much to show for it, the two will explore the vineyards while ultimately searching for their identities.
Written by mystic80
This is the first film to win best screenplay from all five "major" critic groups (National Board Of Review, New York, Los Angeles, Brodcast and National Society Critics), the Golden Globes, the WGA and, ultimately, the Academy Awards.
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Goofs
Continuity:
When Maya joins the boys at the restaurant bar for a drink after her shift, the position of her arm (holding the cigarette) keeps changing from shot to shot during their conversation.
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