Maybe if I think this through out loud I'll end up with a better idea of how I feel about this.

I don't think we need to try to view Fight Club and The Wolf of Wall Street as satire in order to find them acceptable and defensible movies. A retreat to 'it's satire' as an excuse for a movie may not be the right one, or maybe it's a much worse movie than those two that doesn't really deserve the label. (Transformers: Revenge of the Fallen anyone?)

Trying to figure out what the deal is with Fight Club may be why it's so important and so essential. A lot of people love the movie, do we hold it against them if they don't make the most sophisticated reading of it? I think if you asked people if Tyler Durden is a good person they'd probably think 'no' is the 'right' answer. But that's why Fincher makes him so appealing. The movie is a fantasy of male rage and rebellion, and Fincher thinks you want to see the fantasy. Same as he thinks you want to solve an unsolvable serial killer case, or watch a woman get revenge on a douchey husband. Again, you know that the characters involved are not being their best selves, but Fincher knows that the transgressiveness is what people want to see and the tacked-on moral conclusions of older movies are no longer necessary. So people understand why Jack turns into Tyler as soon as they understand why he has to com back to reality, but it's fun while it lasts.

Naturally, real bankers were reported to love Jordan Belfort's shenanigans. They want to see the fantasy. The Wolf of Wall Street isn't so much a satire of a lifestyle as an attempted explanation of why Jordan Belforts exist and why they choose to live the way they do even though the wealth and lifestyle doesn't seem to make them happy people.

I'll throw one more movie in the ring here: Pain&Gain. Is it satire? Or is it an outright condemnation of stupid people who watch too many movies trying to achieve their American Dreams? In other words, the audience of the movie. You wouldn't want to end up like the characters in Pain&Gain, but you understand them, and the movie pities them.

It's same with Fight Club. The audience for the movie is the same as who the main character is, so it doesn't go about scolding him for being who he is, it just shows what happens when his fantasies go to far. It doesn't condemn him or offer alternatives because there are none.