Another strong appeal of the character to Giamatti was Miles’ yin-yang relationship with Jack – a rare, intimate portrait of male friendship and all its conundrums. “There’s a bit of a Laurel and Hardy thing going on with Miles and Jack, but there’s also a lot you can relate to in their relationship,” he says. “I think a lot of people do have these kinds of friendships, maybe with someone they met in college, where there’s a very strong, almost mysterious bond, even though it’s not always clear why the friendship has lasted. The main thing about Miles and Jack is that they stick together because they get something from each other. Sure, they have their jealousies and conflicts, but Miles gets a kind of vitality from Jack and Jack gets a certain grounded-ness from Miles. And now suddenly, here comes a time of change in their friendship, which they are not necessarily ready for.”
In the film, Payne follows Miles with a revealing intimacy, giving audiences access to his most prosaic -- and often telling -- moments, from making a drunken, pleading phone call to his ex-wife or rushing to the bathroom to splash water on his face at a crucial juncture in the middle of his first date with Maya. “It is in the most mundane moments where we find the keys to Miles’ personality,” says London. “Paul reveals these small moments with an honesty that resonates with all of us.”
Perhaps the most intimidating part of the role for Giamatti was the unfolding relationship between Miles and the alluring waitress Maya, played by actress Virginia Madsen. “I kept thinking ‘no one’s going to buy a man like me making out with her,’” laughs Giamatti. “But she was so wonderful as Maya that she set me at ease. There is something so simple and direct about her, and so grounded, it became easy to see how even Miles might have been carried away in that moment.”
With Miles cast, it remained the filmmaker’s challenge to match him with an antithetical yet compatible Jack. Alexander Payne had invited Thomas Haden Church to audition, having seen the actor before in previous auditions and having wanted to cast him in the right role. Jack, felt Payne, was clearly that role. “Once I saw him audition, I just couldn’t imagine anyone else in the part,” comments the director. “His humor, his craggy and handsome looks, his goofiness and the fact that he also had a lot of experience in TV, all had an interesting crossover with the character.” The filmmakers were also seduced by Church’s innate likeability, which seemed to perfectly mirror the very essence of Jack. “Thomas is so charming that he can get away with all kinds of bad behavior and still have you like him,” Michael London notes. “No matter how misguided or deluded Jack might be at times, you find yourself forgiving him because of how Thomas plays him with a kind of sweet vulnerability.”
For Church, the role hit close to the bone. “I probably am a lot more like Jack then I’m even aware,” he muses. “There are so many things about his back story that really resonate with my life -- it was easy to drop an anchor right in the middle of Jack’s story and have plenty of ballast. Jack’s a guy who’s in his 40s and has reached a kind of resignation about his life – professionally, emotionally and relationship-wise. And what’s interesting is that on this trip he’s trying to find a way to buck all that off for one week, with disastrous results.”
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