Casting the lead roles was especially critical, because, as Foster explains, Waking the Dead is a film "about a man whose dreams are about to come true. Fielding is about to become everything he's always wanted to be: a leader, someone who can make a difference, someone who stands for something. But, under the glare of the microscope, his past starts to haunt him. He keeps seeing the woman he loved, the woman he's never been able to let go of, the woman who died 10 years ago. With each apparition, his world begins to unravel. His mind takes him more and more deeply into the past, until he can't tell whether he is self-destructing or finally coming to truth and closure. We realize, through his intense journey, that this is precisely the kind of man we would want representing us in government: someone attuned to the pain and complexity of the human struggle."
The two leads would have to incarnate the guiding force in the story: a love so deep, it transcends death. Foster says, "I was particularly drawn to the romantic story of the film. There are people in our lives who we have loved so deeply, so profoundly, that they inhabit us forever, like soul mates. In Fielding's case, Sarah is taken away from him before he even has a chance to assume his own identity. Without closure, he continues to be haunted by her."
During the casting process, one actor in particular was brought to Gordon's attention: Billy Crudup. Gordon remembers, "I wasn't really familiar with his work, but people I trust were, and brought him to my attention. I was told he loved my script, and wanted to meet me to discuss it. I did as much research as I could on him, and went to New York. When we first met, I thought, 'Well, he has the right look.' Ultimately, it boiled down to spending about five hours together in a room -- sort of the world's longest and most personal audition: we just sat there, reading, trying stuff, and playing. I knew that what we needed, more than anything, in a character this complex was an actor who'd have a sense of adventure, a sense of bravery, and would be willing to go out on limbs. I watched a tape of 'Arcadia' (a play that won Billy many awards). It was amazing, and so, between the work he did with me, and seeing the quality of his theater work, I thought, 'Okay, I'm ready. I'll take the leap of faith."
Kleinman, too, was sold: "Billy's one of the best actors to come along in a while. He has this combination of vulnerability and strength. He's certainly good-looking, but he also has this remarkable intelligence that shines through. He understood the story. His role is a very difficult one. On the one hand, Fielding Pierce is a very charismatic, Robert Kennedy-esque politician. But, on the other hand, he's someone who's incredibly tormented, in a very spiritual, inner way. There are two movies going on simultaneously here. Billy, with his enormous range, was able to do both -- brilliantly."
For his part, Billy Crudup was drawn to Waking the Dead as soon as he read the screenplay, because of "the way in which the love story was told. It was lyrical and ethereal. The storytelling wasn't linear: it goes back in time and you learn about the characters. There was a level of suspense -- not about people being chased, but more about learning about them in the midst of enormous changes in their lives."