I didn't know very much about Alfie before I saw it. I expected it to be a swinging 60's comedy about a charming ladies' man blah blah blah. It really wasn't that. It was something so much better. This movie actually comes down really hard against Alfie's choice of lifestyle.
Alfie, played by Michael Caine in one of his career defining roles, only thinks he's a charming ladies' man. He drifts from woman to woman, ditching them without a moment's thought if they show any signs that they're growing attached. His perceived perfect life begins to show cracks when one of his girls gets pregnant. Against his better judgment, she keeps the kid, and he finds himself acting as a weekend dad. He takes to it for a while, but is still unwilling to commit to the kid's mother, and is thus kicked out of the relationship. Not long after that, a health scare gives Alfie his first glimpse at his own mortality, which only persuades him to continue his attachment-free lifestyle with even more reckless abandon.
Caine as Alfie is all bravado. He acts cocky and confident, and addresses the camera like he has all the answers. He is a man without any respect, for women (he dehumanizes them by calling them 'birds' or even referring to them as 'it'), for other men, for social structures, or for himself. He constantly breaks the fourth wall and even basically tells the opening credits to fuck off, showing us that he has no respect for the established rules of moviemaking either.
How can anyone respect a man without any respect? They can't, and it's a slap in the face for Alfie when that fact is bluntly laid out before him. We as the audience can't respect Alfie, either. Instead, he's an object of pity, a shallow man who runs away from everything of substance ever presented to him.
This was the first time I had ever seen young Michael Caine at work. I think the oldest Caine film I had ever seen before this was Dirty Rotten Scoundrels. You can see how he became such a huge star. Just like the women he seduces, Alfie draws you in with his superficial charm and wit, then pushes you away with his crass and insensitive behavior towards others.
Lewis Gilbert directed Alfie, and it's quite an accomplishment, though I find it fascinating and a bit confusing that he would make a movie decrying this sort of lifestyle and follow it up with You Only Live Twice, in which James Bond lives pretty much exactly the same way, but with none of the consequences.
In the end, after hurting a lot of people with his selfish ways, Alfie himself suffers a series of personal blows, and you could say he learns a lesson, but the movie doesn't tell you for sure if he has changed his behavior for good. He's not a young man, and he's pretty set in his ways, and it may be too late for him.
Alfie (the movie, not the character) is funny, thoughtful, and full of compassion. Not only compassion for the women who fall victim to Alfie's charms. There's even a little compassion left over for Alfie himself, who thinks he has all the answers, but really has not a one.