Sideways (novel)

2004 novel by Rex Pickett

Sideways is a 2004 novel by Rex Pickett. The novel is the first in the Sideways Trilogy.

The novel is the story of two friends, Miles and Jack, who take a road trip to the Santa Ynez Valley AVA a week before Jack plans to marry. Miles is a recently divorced wine aficionado who struggles to publish his novels. Jack is a charismatic television director who is determined to engage in a short affair before his marriage.

In 2004, the novel was made into a film, Sideways, directed by Alexander Payne. The film received critical acclaim, and won the Academy Award for Best Adapted Screenplay in addition to being nominated for Best Picture, Best Director, Best Supporting Actor (Thomas Haden Church) and Best Supporting Actress (Virginia Madsen).

A self published sequel to the original novel entitled Vertical and written by Rex Pickett was released in September 2010. Payne has indicated that he is not interested in directing a sequel to the film based on Vertical. Fox Searchlight owns the rights to the characters, but Payne's lack of interest makes the film a non starter for Fox. A third novel, entitled Sideways 3 Chile, focuses on Chilean wineries and was published in 2015.

A straight play adaptation of the novel is available for licensing from Concord Theatricals. The show premiered at the La Jolla Playhouse in 2013.

A musical adaptation of the novel premiered in 2021. The show has a book by Pickett with music by Anthony Leigh Adams and lyrics by Pickett and Adams.