I think what gorillathehun said is a big part of it. I'm sure at least some of you guys (gentlefolk? forumaniacs? I'm new to forums) are familiar with the YouTube channel WatchMojo. For the uninitiated, their thing is Top 10 lists of pretty much anything you can imagine. For a while, these lists were pretty typical: top 10 video games, top 10 horror films, top 10 rappers, etc. Lately, they've had to come up with some rather esoteric lists to avoid repeating themselves, which of course has a lot of people complaining.
I think Cracked is having the same problem. They've just been in the game so long, they're finding it hard to stay fresh. This happens everywhere, be it in companies, community groups or continent-spanning empires. They found a comfortable niche, occupied it and are now facing the difficult problem of having to find ways of branching out to reach people outside their demographic without (hopefully) alienating those that are already reading. When your readership is in the hundreds of thousands or millions, every change is going to make somebody angry, and every large move - focusing on social issues, for instance - is going to make a lot of somebodies angry.
I'm admittedly not too happy with Cracked these days, but I do understand it must be a bit of a precarious situation to be in, which may also explain some of the perceived hostility coming from Wong and the Gang.