First off, let me say that I'm glad I didn't stay home to watch the Ohio State/Florida basketball game, as Ohio State got killed and lost by 20 points. I can say with some certainty that I did not miss much.
Shepherd is Robert De Niro's fictional origin story of the CIA, tracing the spy organization from its humble beginnings as the OSS during WWII to its botched invasion of Cuba with the Bay of Pigs fiasco in 1961. The film follows the fictional career of Edward Wilson, a composite character who went to Yale and was a member of the infamous Skull & Bones boys' club. (They can call it a secret society if they want to, but we all know it's nothing more than a bunch of drunk frat boys playing dress up.)
Recruited by the FBI, Wilson (Matt Damon) shows an aptitude for this whole spy game by turning in a professor believed to be a member of a group of Nazi sympathizers. After America enters the war, he's sent overseas to help set up a counter-intelligence operation.
Prior to going overseas, Wilson knocks up a buddy's sister (Angelina Jolie's talents are wasted in this cliched role) and does the honorable thing by marrying her. He does not return home until after the war, when he meets his six-year-old son for the first time.
What follows is...more of a cliche, really. Wilson is so devoted to his work at the CIA that his home life is basically non-existent. He ignores the wife and son he never wanted and they live together in a Stepford-family guise for appearance's sake, the All-American happy family that's anything but.
Shepherd clocks in at a hefty two and a half hours plus, much of it filled with Matt Damon trying to look torn and anguished over his job and family, which is not meant to be a knock on Damon, who does a fine job with what he's given, but rather a criticism of the writer, who created this Edward Wilson, the ostensible hero of the picture who we never get a chance to care about.
That, more than anything, is my major problem with the film: I didn't care about a single character. Maybe it's because the movie tries to tell the true story of the CIA, but chooses to do so using a fictional character. Knowing that events didn't take place the way we see them on screen, or, at least, knowing they didn't happen to this guy, it takes away from any sort of emotional attachment we're meant to have.
This guy whose father killed himself when Edward was six, who enters into a loveless marriage because he got her pregnant, whose son wants nothing more than the love and respect of a father who was never around...none of it really happened. The CIA was created without this Edward Wilson's help. He never existed.
If you want to tell a true story, then tell a true story, don't fuck it up with fiction. You can dramatize certain real events to make them more palatable to a film-goers, such as The Insider, but if the core of the film rings hollow, you have a problem.
De Niro is a fine director. Alec Baldwin, William Hurt, Billy Crudup, Michael Gambon, the Russian spy guy, they all had fine supporting performances. But I just...didn't care about any of them, which I guess points toward the writing, because that's all that's left.
Good plot. Good story. Good performances. Lifeless, empty characters.
The first three mean nothing without that last one.