Director and screenwriter Alexander Payne made his big-screen debut directing one of nine vignettes about love and relationships in the 1992 film Inside Out. Four years later, he gained praise and recognition for Citizen Ruth, a bitingly satirical look at the abortion debate which starred Laura Dern as its amoral anti-heroine. In 1999, Payne wrote (with Jim Taylor) and directed Election. A wickedly funny look at American politics through the lens of a high school student council election, the film won rave reviews and further established Payne as one of the current cinema's most cutting directors and satirists. After writing Jurassic Park III, he teamed up with Taylor again for About Schmidt, based on the novel by Louis Begley. A comedy drama about Warren R. Schmidt (Jack Nicholson), a man in his sixties, About Schmidt received several award nominations and won a Golden Globe for Best Screenplay. While About Schmidt may have polarized audiences - some of whom saw it as a meaningful and humorous meditation on ageing while others saw it as little more than a depressing glimpse into the life of an morose old cynic - positive reaction to Payne's subsequent film Sideways was near universal. As with his previous efforts, Payne's scope remained limited in a noteworthy attempt to keep his characters both identifiable and three-dimensional, but audiences just seemed to have a much easier time connecting with an embittered middle-aged writer/wine connoisseur and a sex-crazed has-been actor than they did with an aged and embittered divorcee. If Thomas Hayden Church's loss of the "Best Supporting Actor" Oscar to Morgan Freeman at the 77th Annual Academy Awards coupled with Paul Giamatti's previous loss at the same year's Golden Globes ceremony left fans of the film somewhat cold, they could at least take solace in the fact that Sideways did earn Payne an Oscar for "Best Adapted Screenplay" (an award which the writer/director shared with co-writer Jim Taylor).
Although Payne took seven years to make a follow-up to Sideways, he certainly kept busy. In addition to contributing to the screenplay for Adam Sandler's I Know Pronounce You Chuck & Larry, he directed a segment of the omnibus film Paris, Je T'Aime, and helped produce television shows and movies such as Tamera Jenkins' The Savages. But when he finally got back behind the camera for a full-length feature, the result was The Descendants, a comedy/drama about a wealthy Hawaiian lawyer who discovers that his comatose wife has been cheating on him. The film opened to strong reviews and earned Payne writing and directing nominations from the Academy, the Broadcast Film Critics, the Golden Globes, and the Independent Spirit Awards. He would win the Best Adapted Screenplay award from the Academy.