As promised, here’s the next From the Archives selection from my reporting about Alexander Payne’s Sideways, coverage that grew out of a week I spent on the set of the film. I’m posting this and my other Sideaways stories because Payne is about to be in the news, along with George Clooney, for their collaboration on the film The Descendants, which is Payne’s first feature-length effort as a writer-director since Sideways. A third Sideways story will soon be posted here. This blog also contains several more of my stories on Payne, whom I’ve been covering since 1996, including a couple pieces about The Descendants, the new movie that should be hitting theaters near you between mid-November and mid-December.
From the Archives: A Road Trip Sideways –Alexander Payne’s Circuitous Journey to His Wine Country Film Comedy
©by Leo Adam Biga
Originally published in The Reader (www.thereader.com)
Alexander Payne’s new movie, Sideways, took a four-year road trip from high concept to stalled project to hot property. It finally opens October 20 in a limited national release.
The inspiration for the film came from a 1998 unpublished novel by Rex Pickett, who drew closely from his own life to tell the sad and comic story of two loser buddies on a wine tour.
Adapted by Payne and writing partner Jim Taylor, the film follows best buds Jack, a libidinous ex-soap star, and Miles, a junior high English teacher and would-be writer, in a classic “men behaving badly” tale. On the journey, their addictions, obsessions and neuroses with wine and women catch up with them.
With Payne (Citizen Ruth, Election, About Schmidt), producer Michael London (Thirteen and House of Sand and Fog) got a director who left him little to do but sign off on expenditures, smooth ruffled feathers, keenly eye each day’s “takes” and stay on schedule and on budget. Payne, who also controlled the film’s “final cut,” found London a good fit.
“In terms of working with me and the actors, and then working in an effective way with the studio, he just speaks everyone’s language,” Payne said.
Although Sideways marks the first time London and Payne worked together, Payne was near the top of London’s list to adapt the book to film.
“I was really just a fan of Alexander’s before this. I really didn’t have any particular history or connection with him,” London said. “I’d read an early draft of my friend, Rex Pickett’s novel and we started talking about it as a movie.”
But London knew who and what he wanted.
“It’s not like there’s 50 directors in the world who could have done this story, and I think that’s probably true of most of the things Alexander does. They’re very unique to Alexander,” the producer said. “I was quite obsessed that he would relate to these characters (Jack and Miles) and to the whole idea of this kind of wasted wine trip and of men in mid-life crisis. It just felt like he would do something really special with that. I chased him through his agent and all the ordinary avenues, but without much luck.”
Somehow, despite London’s inability to reach him, the book got to Payne through another source.
“But it wound up sitting in his hands for about nine months because he was finishing Election, and then he was touring and doing press,” London said.
Payne was in Scotland when he finally called London.
“There was a phone message saying, ‘This is Alexander Payne. I just got off a plane in Scotland and I want to do this movie Sideways next.’”
London said Payne felt so strongly about the material that he became boldly proprietary about it, making his directing it a fate accompli.
“From our first conversation he was like, ‘I have to direct this. No one else can direct this.’”
Alexander Payne and principal cast on location for “Sideways”
A Long, Tortured Path
London got the writer-director he wanted, but not as soon as he’d hoped.
“That began a kind of very long, tortured path,” London said, “because as it turned out it was not going to be [Payne’s] next movie. He did Election and then Jack Nicholson committed, sort of unexpectedly, to About Schmidt, and that movie came together much more urgently than he imagined.”
Three years passed from when London and Payne first agreed to make Sideways to the start of production. That wait was extended by delays in the start of Schmidt.
“Every time the schedule got pushed back, he would call me in sort of an embarrassed voice,” London said. “And, obviously, there was no real conversation about taking [Sideways] to anyone else at that point because his passion for it was so great and his connection with it was so complete.”
Then came their initial sales campaign, which showed how quickly things can change in the film industry.
“We went out and took it to a whole bunch of companies,” London said. “It was right after Election opened and everybody wanted it. It was kind of like an auction thing. We set up a deal with a fantastic amount of money for everybody at a company called Artisan, which had then released a movie called The Blair Witch Project. They were the most sought after independent company in the business.”
But fortunes can shift like quicksilver in the movies.
“By the time Alexander had gone off to do Schmidt and come back,” London said, “Artisan was on the verge of going bankrupt, and the company we had sold the rights to, which made so much sense before, no longer had the marketing clout to take care of the movie properly.”
London reminded Artisan, which still wanted in, that neither party was legally obligated to the other.
“We had been quite careful not to sign contracts with them,” London said, “because when it looked like Alexander might go away and make another movie first, just in the back of our minds we thought, ‘Well, we don’t really know what Artisan is going to be like in a couple years.’ We were cautious, and properly so, and that gave us freedom so that when Alexander resurfaced and Artisan didn’t feel like the right home anymore, we were able to work out a departure from them.”
The frustration of putting off Sideways, London said, was offset by the relationship he forged with Payne over that time.
“During those three years I came to know him very well,” the producer said. “Our friendship kind of grew up during those years, which was actually very nice because it meant that instead of being out here shooting with someone I’ve just gotten to know recently, we feel like we’ve been through a couple wars together.”
In the interim, London “went off and did a couple other movies,” and Payne made perhaps his most mature film up to then in Schmidt, a jury selection at the Cannes Film Festival, one of the best reviewed films of 2002 and the filmmaker’s biggest money maker – more than $100 million worldwide.
“It all worked out very well because, by the time he was ready to do it, it was a good time for him and a good time for me,” London said.
Despite the delays, there was never a question Sideways would get made.
“Michael and Rex were hoping About Schmidt would not have come first,” Payne said. “But I just kept promising that I’m going to do [Sideways] next and I kept putting my hand in my pocket every year to renew the option on the book and then I kept to my word. As soon as Schmidt was finished I began work on this one.”
Payne said his experience with About Schmidt laid a needed foundation for his new project. “Because of my experience on Schmidt I think Sideways is a better film than it would have been otherwise,” Payne explained. “Rex said jokingly, but he means it too, that I needed to make a film about maturity before I could go back and make a film about immaturity.”
Packaged Sideways
With Artisan out of the picture, London and Payne hit on a new strategy to package Sideways – use Payne’s hot status to sell a ready-made project that retained full creative control for its makers.
“Instead of selling it, we decided the smarter way to make the movie was to have Alexander and Jim write it on spec and for us to figure out what we thought the right budget and cast for the movie was, instead of allowing the studio to own it and dictate those things,” London said. “Alexander was in a unique position of creative power because he’s riding high right now. The material’s commercial. Financiers knew if they invested in a movie about two guys on a comic journey through the wine country they were probably going to be able to sell it.”
The producer and director put the package together and formed a group to get financing. They used a ballsy, “take it or leave it” approach, and it worked.
“We rolled the dice,” London said. “When we were about eight weeks before we needed to start shooting – we waited absolutely until the last possible minute – we said, ‘OK, who wants to make this movie?’ We took it to the half-dozen or so studios and said, ‘Here’s the movie. This is the script, this is the cast, this is the budget. We hope you love it. If you don’t love it, you shouldn’t make it. Alexander has final cut. We’re not really looking for your input. We’ll listen to your input. Don’t tell us the script is too long, because we know it’s too long. Don’t tell us you think this casting is not starry enough, because Alexander’s met with a bunch of movie stars and he’s decided these are the best actors for the roles.’ And we did that and very quickly weeded out who was really serious from who wasn’t.”
For its cast, Payne originally considered a pair of stars for the juicy parts of Miles and Jack that would have raised the ante and the buzz.
“The star version of this film would have been George Clooney as Jack and Edward Norton as Miles. And I like them both very much. I think they’re both terrific and they both expressed interest in these parts,” Payne said. “And I was tempted. Actually, not with Clooney, and I told him to his face. I said, ‘I think you’re great but to ask the audience that the world’s handsomest, most famous movie star is the biggest loser actor is too much. If you were a loser in some other profession, maybe OK, like in the Coen Brothers movies, but as a loser actor? That becomes a joke of the film, and I don’t think that’s right. He was fine with that. Norton, I thought more long and hard about.”
Payne selected character actors rather than big names. For Miles, he chose Paul Giamatti (American Splendor, Confidence). For Jack, he chose Thomas Haden Church (George of the Jungle II, 3,000 Miles to Graceland, TV’s Wings). The two main women’s roles went to Virginia Madsen (The Haunting, The Rainmaker) as Maya and Sandra Oh (Under the Tuscan Sun, HBO’s Arliss) as Stephanie. Longtime companions, Payne and Oh married in January 2003.
That Payne chose lower-profile actors doesn’t mean he feigned interest in Clooney and Norton so he could placate producers or executives.
“Look, my life would have been easier, and certainly the marketing guys would have an easier time, if I had picked stars,” Payne said. “I met everyone. I met famous, not famous. Bring ‘em on. No prejudice. But, ultimately, I just wanted to really be able to cast the actors that best fit the parts.”
He acknowledged one advantage of a lowered profile.
“It’s not so much that the stars make shooting difficult, but it’s other people’s attitudes toward the stars that can become an obstacle in the shooting’ Payne said.
He said London signed off on his choices with some trepidation.
“He would have, at one time, preferred I selected more famous actors. But now he understands why everything happened the way it did,” he said. “He just couldn’t be happier. He’s only about the quality of the film and not about making it more commercial, although I know he likes me to make commercial choices.”
Sideways is more a love story than Payne or London ever imagined. The romance was evident on the shoot and in dailies, the footage shot in a day. It became even more obvious during post-production.
The film follows best buds Jack and Miles on a central California wine country road trip that’s sidetracked after they meet Stephanie and Maya. Although Jack, a shallow, oversexed actor, is about to be married, he pairs with Stephanie, a wine-pouring hottie from a winery tasting room. He doesn’t tell her about the upcoming wedding, and he dismisses Miles’ warnings.
Miles, a smart, neurotic writer obsessed with his ex-wife, resists involvement with “another woman.” But he finally falls for Maya, an empathetic waitress who shares his appreciation for fine things, especially wine. When Stephanie discovers Jack’s deceit, she exacts revenge in a classic “hell hath no fury like a woman scorned” manner. When Maya learns of the deception, she blames Miles because he should have stopped Jack’s charade.
To Jack, Haden Church brings a laidback personality, rugged blonde looks and mischievousness. For Miles, Giamatti’s intellectual air, shy reserve and world-weary demeanor perfectly capture the character.
A single scene sold Giamatti on the project.
“When I first met him (Payne) and auditioned for it, I hadn’t read the whole script. I just read what they sent me, which was the scene where Miles talks about why he loves Pinot Noir so much,” Giamatti said.
In a soliloquy to Maya, Miles explains his “thing” for Pinot Noir and unknowingly describes his strengths, weaknesses and needs:
“I don’t know. It’s a hard grape to grow. It’s thin-skinned, temperamental, ripens early. It’s not a survivor like Cabernet that can grow anywhere and thrive even when neglected. Pinot needs constant care and attention and, in fact, can only grow in specific little tucked-away corners of the world. I mean, it just amazes me that only the most patient and faithful growers can uncover Pinot’s fragile, delicate qualities. And if you get the right combination of soil and sun and love, then you can coax Pinot Noir into its fullest expression. And only then, its flavors are the most haunting and brilliant and subtle and thrilling and ancient on the planet.”
“I just thought the whole idea of the obsession of wine was such an interesting theme for this guy,” Giamatti said. “There’s this kind of constant striving for transcendence through the wine and the wine milieu, and it just keeps collapsing in on the guy because he’s such a wreck.”
Running through women like a serial seducer, Jack cheats on his bride-to-be, lies to his mistress and gets caught in the act with a waitress he picks up. Running away from women like a scared boy, Miles, who ruined his marriage with an affair, hassles his ex-wife, steals from his alcoholic mother and lets Maya down.
Jack and Miles make an odd twosome in some ways and a perfect pairing in others.
“It’s a real like Laurel and Hardy thing in a way,” Giamatti said. “It has those two complementary yin and yang sides, and they shift back and forth, too. I’m the straight man and then sometimes I’m not. It’s an unlikely pairing but it has definite resonance. It’s a tricky thing whether people believe these two guys are friends. But I think among men friendships like this are not uncommon.”
Haden Church said, “I think they’re both oblivious to the strains of juvenile behavior.”
Madsen plays Maya with once-around-the-block common sense and simmering, ready-to-ignite sensuality. Oh, as Stephanie, captures her character’s vitality and toughness.
Payne was particularly struck by Giamatti, whom he called “a really great actor.” Payne feels this film could propel Giamatti and Haden Church, who nail “two really good parts for actors,” to major stardom. That happened to Reese Witherspoon after she co-starred in Payne’s Election. Payne likes a “sense of discovery” about actors.
“Who were Elliott Gould and Donald Sutherland in 1970 when they did M*A*S*H? Now, when you think of that film, you say, ‘Who better?’ They became stars. I think that’s more fun,” Payne said.

The American Male
A combination buddy picture, road picture and romantic comedy, Sideways has much to say about male bonding and mating rituals. Jack and Miles display two different sides of the modern American male.
“He is two people now,” Oh said. “He is the man who refuses to grow up, right? And he’s the man who refuses to take a stand. So, this is really what we’re seeing. Jack and Miles are the two sides of the American male today.”
“And I think it shows in a very peripheral way what the result is for the American female. Stephanie comes from a long line of women embittered by hard luck with men. When she punishes Jack, there’s going to be so many women going, ‘Whoo-whoo!’ You know what I mean?” she said. “Maya’s the more advanced of the two, but she’s had her own deal with men, and she’s moved onto a place where she can still leave the door open.”
So what begins as a wine-tasting tour becomes a misadventure for the repentant, if unreformed, Jack and a romantic catharsis for Miles. Along the way, Jack and Miles’ friendship is strained and transformed.
Working with Payne
Sideways marked the first time any of the lead actors worked together or with Payne. The actors spent two weeks in rehearsal with their director, a process Giamatti said was as much about “shooting the shit and indulging in good food and wine” as work, although Haden Church said they did read the entire script and discussed scenes, plot points and characterization
After two weeks of rehearsals and 10 weeks of shooting, they were left impressed with Payne and his processes.
“He tries to make you feel as natural and comfortable as possible,” said Oh, who, until now, had only watched him work with others.
“And I really like how incredibly specific he is when he’s directing me,” Madsen said. “He says things like, ‘You know, when I was watching the movie just now I asked myself why didn’t I believe that.’ And he’ll pick out the part he didn’t believe and he’ll give you a change or give you a new note on that specific change or give you a new idea to use.”
It all gets back to trust, which is everything in the actor-director collaboration.
“I trust Alexander innately because of his films. He’ll do whatever serves the movie,” Haden Church said. “He’s had a great career. He’s critically lauded and commercially embraced. He’s one of those icons, especially with young, fickle film audiences. They love his work. So, whatever he’s doing, his process works. It gets the desired results.”
Test of Time
Even without stars, Sideways grew from the time London and Payne joined forces to when they finally signed with Fox Searchlight Pictures.
“The movie had gotten bigger. When we were talking to Artisan we were going to make it for $7 to $10 million — on a shoestring. After Schmidt, Alexander now had the power that we could actually get a healthy budget and do it on a larger scale without compromising,” London said. “It was budgeted at $16-$17 million for a 50-day shoot, which by the standards of contemporary studio movies is a tiny, tiny movie, but by the standards of a movie about a couple guys running around in wine country, is plenty of money to do it well and plenty of time do it well.”
More money means more of everything for a movie.
“It’s having more time, more crew, more resources,” London said.
As much as Payne enjoys shooting a film, there are the inevitable hassles and unavoidable grind that come with working on location over many weeks. Take after take is recorded. Before a movie is ready for screening, the whole post-production phase unfolds. The shooting phase is all about getting to that point.
“Shooting is just harvesting shots to edit,” Payne said.
Principal photography wrapped last December in the Santa Barbara area, and the film netted strong reviews from its Toronto International Film Festival premiere last month.
Payne enjoys losing himself in the editing suite. There, alone with his precious images and away from distractions, he can finally see what he’s got and shape the movie into the form it tells him to take. Payne and Kevin Tent, his long-time editor, collaborate to find the nuances, rhythms, grammar and subtext they hope will make the film warmly referenced and regarded.
The Sideways team envisions the film as a potential modest hit in the near term but as a “stand the test of time” project – one of those films with legs well after its initial release.
“We would like the financiers to make back their money and we would like it to be a beloved movie that lasts a really long time,” London said. “We would trade an awful lot of short term success for this to be a movie that 30 years from now people say about, ‘God, do you remember that movie about those two guys?’”
In a story all about detours, the making of Sideways may have taken the most unexpected path to become a charming, hip success.
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