Not sure, really. I tried to rewatch it a while back and just couldn't latch on to anything.
I think when it came out it was a little bit shocking and naughty, what with all the fellatio and mud and people being fed to pigs and swearing. It also had that crazily, hilariously overwritten dialogue, which was created by David Milch ad-libbing repeatedly to furiously transcribing interns. And Swearengen was an awesome bad guy.
It was possible to take it seriously then, but all the weak points are a bit too obvious on a later viewing. I don't think it has aged too well. The only thing that stands out in my mind as a high watermark is the unbelievably brutal fight between Dan and Hearst's man.
Speaking of which (warning: graphic violence)