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
Thomas Haden Church' had left film acting, concentrating on voiceover work, when he received a phone call from Alexander Payne to audition for the role of Jack. Church was a finalist for a role in
About Schmidt, another Payne film, and Payne wanted to use the actor in one of his films.
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Goofs
Errors made by characters (possibly deliberate errors by the filmmakers):
In the scene at the bowling alley, the woman at the table with Miles (Sienna's grandmother?) is smoking. Smoking indoors is illegal in California (although it is possible the bowling alley simply was not enforcing this rule).
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"FEARLESS LOVE"
Written by Dillon O'Brian Performed by Bonnie Raitt Courtesy of Capitol Records Under license from EMI Film & Television Music
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