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. —IMDb
Constantine Alexander Payne (born February 10, 1961) is an American film director and screenwriter. His films are noted for their dark humour and satirical depictions of contemporary American society.
Payne, a Greek American (his grandfather’s family name was Anglicized from Papadopoulos), was born in Omaha, Nebraska to parents who were restaurant owners. He was the youngest of three sons and grew up in the same neighborhood as billionaire Warren Buffett. Payne attended Creighton Preparatory School high school and later Stanford University, where he double majored in Spanish and History. As a part of his Spanish degree, he studied at the University of Salamanca (Spain). Payne got his MFA in 1990 from the UCLA Film School.
Payne worked in various capacities on films and television before he wrote and directed his first full-length film Citizen Ruth in 1995. His film Election, starring Matthew Broderick and Reese Witherspoon, which takes aim at politics… read more
I found the ending to this film to be so incredibly moving, it's what pushed me into loving it. Paul Giamatti and Thomas Haden Church were both fantastic and the story had a very good balance of subtle humor and heavy drama. The characters and writing in this film are extraordinary. They felt very flawed but relatable very real. Loved this movie. Oaky.
Totally agreed; people don't give Payne enough credit for his understanding of people.
Agreed. I've found all three of the Payne films I've seen so far to be incredibly human. He really knows how to craft incredible characters.
an all-time favorite comedy of mine. a fantastic film with lots of laughs. the writing is exceptional as well......
I’ve been thinking about Sideways for several days, the need to see it again. Soon. I embrace and cherish this remarkably insightful film about friendship and faltering dreams.
These thoughts… read review
One of the most delicious mixes of drama/comedy I’ve ever seen. Paul Giamatti and Thomas Haden Church are pitch perfect in their roles and really make you believe you are watching two old friends… read review