Sideways is a 2004 comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. Adapted from Rex Pickett's 2004 novel of the same name, Sideways follows men in their forties, portrayed by Paul Giamatti and Thomas Haden Church, who take a week-long road trip to Santa Barbara County Wine Country.

Directed by Alexander Payne, Sideways follows Miles (Paul Giamatti), who is distressed about his lack of success as a novelist, and Jack (Thomas Haden Church), an equally unsuccessful actor with a rapidly approaching wedding. In a last-ditch effort to sow their wild oats, Jack and Miles take off on a final road trip to California's wine country the week prior to Jack's wedding. Both men have goals for the vacation -- Miles wants to turn Jack on to the art of wine tasting, while Jack is concerned with exploiting his last days as a bachelor -- but when the two men come across two fascinating women (Virginia Madsen and Sandra Oh), the duo is forced to examine their morality, and if maturity isn't such a depressing prospect.

Time Out London said the film was "intelligent, funny and moving", and the Chicago Sun-Times' Roger Ebert, giving the film four stars, said, "what happens during the seven days adds up to the best human comedy of the year - comedy, because it is funny, and human, because it is surprisingly moving." The review aggregator Metacritic gives Sideways a Metascore of 94%, signifying "universal (critical) acclaim." The movie also holds a rare 96% rating at Rotten Tomatoes with 206 positive reviews out of 213.

Throughout the film, Miles speaks fondly of the red wine varietal Pinot noir, while denigrating Merlot. Following the film's U.S. release in October 2004, Merlot sales dropped 2% while Pinot noir sales increased 16% in the Western United States. A similar trend occurred in British wine outlets. Sales of Merlot dropped after the film's release possibly due to Miles' disparaging remarks about the varietal in the film.

Payne and Taylor won multiple awards for their screenplay. Giamatti and Church, as well as actresses Virginia Madsen and Sandra Oh, playing local women who become romantically involved with the men, all received accolades for their performances.

Sideways won the Academy Award for Best Adapted Screenplay, and was nominated for four other awards, including Best Picture, Best Director (Alexander Payne), Best Supporting Actor (Thomas Haden Church) and Best Supporting Actress (Virginia Madsen).