In 1999, Rex Pickett, a sometime screenwriter and unpublished novelist in Los Angeles, finished a novel about two middle-aged men going to Santa Barbara County to visit wineries during the week before one of them gets married. It was Pickett’s second novel. The first went unpublished, but this one seemed like it just might have a shot.
It didn’t. Pickett’s agent submitted it to film producers and book publishers alike, and the book was utterly rejected. Nobody wanted it. Until… Alexander Payne’s agent’s assistant read the unpublished novel and recommended it to Payne’s assistant, who raved about it when he passed it on to his boss.
Payne was smitten with the book as well, and immediately optioned the book (purchased the rights for a limited time). A production company was lined up and things were moving forward when the nearly inevitable happened and everything came to a grinding halt—no publisher wanted to publish the novel. It’s a bit difficult to do a movie based on a book when the book doesn’t exist.
Payne went on to make About Schmidt (2002), but then in 2003 circled back to Pickett’s novel and managed to move forward with producing the film version, even without a publisher for the novel. Pickett’s book agent sent the book out again. And guess what? They got 100 more rejection letters! Finally, St. Martin’s Press bought the book for $5,000—a pittance, really.
The novel was published four months before Payne’s film of it was released.
The reaction to both the book and the film was sensational, and not just in the entertainment industry. Sideways was nominated for numerous awards (winning the Oscar for Best Adapted Screenplay), and was an enormous commercial success. Meanwhile, its praise of Pinot Noir and disdain for Merlot drove both grapes and their wines racing in opposite directions of popularity.
In Sideways, and indeed in all of the films on this list, Payne explores a familiar theme in his movies: the crisis point of a person’s life—that moment when the cumulative misdeeds and untaken opportunities finally pile up on a person and force them into a complete reexamination of their life (often comically disappointing) and assessment of what to do next.
Sideways is one of my favorite comedies of the past twenty years. Thomas Haden Church is Jack Clark, a slightly past his use-by-date actor, and Paul Giamatti is Miles Raymond, a depressed, failed writer and high school teacher. They drive up from Los Angeles to Santa Barbara County for the week before Clark’s wedding. Clark is what my mother used to call “a roué.” (Look it up. It’s a good word.) Lots of desultory conversations, bad decisions, random sex, discussions about wine, and one of the funniest chase scenes ever. With Sandra Oh and Virginia Madsen. Don’t miss this one, and if you haven’t seen if for a while, time to rent it again.
Ever notice that the character George Clooney always seems to play in almost every movie is: George Clooney, Incredibly Handsome Man? There are two movies in his career, however, where he really shone as an actor, and in both cases he didn’t play George Clooney, but played a vulnerable and somewhat defeated middle-aged man. The two movies are Up In the Air (2009) and this film. Clooney is just wonderful as a man beset by a wife who was paralyzed in a boating accident while cheating on him, a pair of unruly teenage daughters, and the responsibility of managing a vast, undeveloped estate in Hawai’i. I saw this movie three times in the theaters; that’s how much I liked it.
This movie was a box office bomb and has sort of been forgotten, but it’s a real gem. Reese Witherspoon is an annoyingly-ambitious high school junior and Matthew Broderick is her woe-begotten social studies teacher. The action concerns a student body election. It’s yet another based-on-a-novel film by Payne, and received a Best Adapted Screenplay nomination, the first of three such nominations for Payne. Witherspoon is particularly good in this movie.
A cranky, aging father (Bruce Dern) and his good-natured son (Will Forte) go on a trip from Montana to Nebraska to collect a sweepstakes prize the father mistakenly thinks he won—which everyone else, including the son, knows he didn’t. It’s called humoring dad. I’m familiar with the concept. Every year my kids all nod along with me that this year the Minnesota Twins will win the World Series. Filmed in black and white to emphasize the bleak nature of the quest, this film features stellar performances by Dern and Forte.
Want a good cry? Want to sit down and watch a movie and get swept up in some characters in a simple, sad story and then sit there alone in the darkness sobbing to the closing credits? Here’s the movie for you. Jack Nicholson is a retired actuary for a life insurance company, and as he surveys his life he finds nothing but disappointments everywhere. And then he gets a letter from an orphaned child in Tanzania whom he has sponsored. Cue: Tears. Bonus: you get to see Jack Nicholson shopping for groceries in his bathrobe, living out every single man’s fantasy.
David Raether is a veteran TV writer and essayist. He worked for 12 years as a television sitcom writer/producer, including a 111-episode run on the ground-breaking ABC comedy “Roseanne.” His essays have been published by Salon.com, The Times of London, and Longforms.org, and have been lauded by The Atlantic Magazine and the BBC World Service. His memoir, Homeless: A Picaresque Memoir from Our Times, is awaiting publication.