After the release of About Schmidt, which scored Nicholson an Oscar nomination, Payne could have cast almost anyone he wanted in Sideways. ''A lot of big-name actors chased this movie,'' says London. ''We heard from the representatives of everyone: George Clooney, Edward Norton, Johnny Depp, Russell Crowe, Brad Pitt. They all expressed interest.'' But Payne didn't want to cast a star simply for casting-a-star's sake. ''With Election, I had to first offer it to Tom Cruise and Tom Hanks, who were never going to take it in a million years,'' he says. ''That's a process I didn't want to repeat. I understand the insurance policy of having extremely famous people in your film, but I understand comedy more.''
In Payne's mind, the audience wouldn't buy a giant movie star playing an actor like Jack, who's drifted from soaps to commercial voice-overs. ''I told that to Clooney's face,'' he remembers. ''We had lunch together at Bob's Big Boy. I said, 'To ask the audience to believe one of the world's most handsome and successful movie stars is now playing one of the world's biggest loser actors is too much. That would become the joke of the film.' And he was cool with that.''
Having already decided to cast his wife, Oh (Under the Tuscan Sun) — a well-regarded actress in her native Canada but hardly a household name here — Payne zeroed in on Giamatti for the role of Miles. The hangdog character actor proved he could carry at least a small film with last year's indie hit American Splendor, but he was not exactly a financier's dream choice. ''When Alexander offered it to me, I thought he was kidding,'' Giamatti says. ''I kept thinking to myself, Dude, nobody's going to want to make your movie. And who the hell is going to want to watch a movie about wine?''
Looking to fill the role of Jack, Payne remembered Church, who had auditioned unsuccessfully for both Election and About Schmidt. Like Jack, the lantern-jawed Church achieved early stardom — as the dopey mechanic Lowell Mather on the sitcom Wings — only to see his career drop off. ''From about 1993 to 1998, I was as famous as you can be as a TV star,'' Church says. But when the sitcom Ned and Stacey was canceled after two seasons, he tried in vain to launch another series, and his acting career slowed down. ''I got offered some very impressive things, like Sports Night, but I didn't want to do somebody else's show. I wanted to do my show. And it didn't work.'' By the time Sideways came around, Church was spending most of his time on his ranch in Texas. ''On some level, I had waved goodbye to acting,'' he says.
Payne auditioned dozens of actresses for the role of Maya, the waitress who falls in love with Miles against her better judgment. Finally, he settled on Madsen, who, while respected for her work in film (Candyman, The Rainmaker), had never quite clicked with, as she puts it, ''the money people.'' ''It's not like Virginia was an unknown quantity,'' says London. ''She's a face people know. But to get to reinvent someone as talented as her has been really special.''
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