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.

[2] 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).

[3] A self-published sequel to the original novel entitled Vertical and written by Rex Pickett was released in September 2010.

[4] A third novel, entitled Sideways 3 Chile, focuses on Chilean wineries and was published in 2015.