It can neatly be summed up in one word: Depressing.
If you want to laugh, or even just smile, don't bother watching. Matt Damon's character, Edward Wilson, fails in every way.
The movie's website advertises the film as follows:
Matt Damon, Angelina Jolie and Robert De Niro star in this powerful thriller about the birth of the CIA. Edward Wilson (Damon) believes in America, and will sacrifice everything he loves to protect it. But as one of the covert founders of the CIA, Edward's youthful idealism is slowly eroded by his growing suspicion of the people around him. Everybody has secrets...but will Edward's destroy him? With an all-star cast including Alec Baldwin, Billy Crudup, William Hurt, Timothy Hutton and John Turturro, it's the gripping story David Ansen of Newsweek hails as "spellbinding."
It sounds gripping, but I didn't find the movie nearly as compelling as the synopsis.
Wilson, the main character, did not appear idealist, enthusiastic, or willing to sacrifice anything. Rather, he seemed to be a robotic yes-man, constantly seeking approval (just as his son later does in the movie) - not so much a dreamer as a droid.
The movie goes like this:
"Hey, we want to you be in Skull and Bones"
"Hey tell us your darkest secret"
Girlfriend 1: "Sleep with me!"
Random Girl at Party: "Make a baby with me: NOW!"
Girl's Brother: "She's pregnant, marry her."
CIA Founder: "Be a CIA Agent"
CIA Founder: "Go to Europe now"
Random European Woman: "Sleep with me!"
I will note that Damon's character supposed to be known for his cold, stone-faced, emotionless nature. Damon did a good job playing the role. But none of Wilson's actions ever were his own. He always moved, spoke, acted in response to someone else. I think the only free action he ever does is ask his wife to name their son after him. (And how uncreative is that?)
The movie is an interesting one to watch if you're into psychology and want to analyze father-son relationships. There's certainly a lot of good material there.
It's also a great movie to watch if you need a guide to: 1) Why you should not randomly hook up at parties, 2) How to be a bad husband, and 3) How to be a really bad father.
The movie reminded me of one of those depressing "classic" novels you read in high school just to pull apart literary themes, devices, allusions and the like. If you would like an exercise that, then watch the movie. From that standpoint it's well done and certainly has far more substance than your average flick; but be warned: this ranks as one of the most depressing, soul-killing movies I have ever seen.