The problem with making a film about a dry character is that those qualities can rub off on the film itself. Matt Damon's Edward Wilson is that kind of dry character, and The Good Shepherd is that kind of dry film. There's much to admire in Robert De Niro's ambitious first trip back to the director's chair after 1993's A Bronx Tale. The years from the 1930s through the 1960s are recreated with impeccable period detail, and the plot isn't too hard to follow, a potential stumbling block with spy films that feature numerous characters and numerous shifting allegiances. No, the biggest problem about The Good Shepherd is that Damon fails to generate interest in his character, a man known for being meticulous and humorless -- characteristics that have been attributed to the Central Intelligence Agency, so it's no surprise Wilson (modeled on James J. Angleton) was one of its founders. The details of Wilson's life are downright sensationalistic. His father committed suicide, and he has a wildcard son whose incautiousness could compromise national security. But the character is so rigid, so closed off from his emotions, and so frequently passive in the events of his life, it's hard to feel for him the way De Niro intends. This shouldn't be blamed on Damon; the supporting cast is filled with Hollywood heavyweights who are similarly incapable of making an impression. The most curiously misused performer is Angelina Jolie, whose aggressive seduction techniques introduce her into the proceedings as a much-needed firecracker. But she quickly blends into the scenery as a long-suffering wife, yearning in ways that just don't resonate. Ultimately, De Niro's removed approach may keep the film from being more interesting. At 2 hours and 47 minutes, The Good Shepherd becomes a tough slog that's easier to respect than like.