By far.

Um, yeah.
It goes:
The Basses
The van der Woodsens
The Archibalds
The Waldorfs
The Humphreys

It's seriously becoming werid. I mean, the Uncle has been with the Dad's wife/girlfriend (still confused about that whole Elizabeth thing), and said Uncle also wants his nephew's girlfriend. Then you have the whole 'is the mother dead or alive?' thing. Oh, and also the fact that the dad is dead tops it all of.

After that, it is def the Archibalds. The dad was/is? a drug addict, they have gone broke, and have a craaazy manipulative grandfather.

Then VDW, then Waldorfs and then Humphreys.

No doubt.
And although Blair was probably the first to struggle with her mother, the Waldorfs and the Humphreys are the most functional at this point. Maybe the Waldorfs even more, because the Humprhey's have a lunatic daughter, a love-blind-loosing-his-edge-father and a son who's knocked up an awesome bitch.

The Archibald's/ Van der Built's: Howard committed embezzlement & fraud, became a drug addict, tried to kill himself and Anne just pretended it didn't happen. Also they went broke, Anne never realized that Nate prostituted himself to keep them afloat & Howard tried to kidnap his own son and wife. Nate's grandfather practically controls the whole family & he was the one who told the police about his son in law, he didn't help his own daughter & grandson when they had nothing after Howard disappeared. And I don't even want to start about Tripp.

The Bass's are pretty messed up too, same goes for the Van der Woodsen's.

I think the Waldorf's & the Humpfrey's are not that messed up. It's not that unusual for parents to get a divorce (if if it is a messy one.)

They aren't all lucky but poor Chuck ...

If Chuck Bass is the most normal person in your family, that a pretty messed up family. The Archibald's are also messed up. The Humphrey's are also bad too. But crazy and evil uncle jack and mother Bass coming back from the dead makes them the most messed up family on the show. I don't even think Dr. Phil can save this family.

JENNY = Drug dealer, bitch, boyfriend stiller (still she's one of my favorite caracter)
DAN = Possible-daddy-to-be (from a crazy evil mother)

or obviously the Bass, but they are supposed to be messed up so

The archiblads dont have a problem anymore..u see nate doesnt have any family problems anymore..so probably it was chuck and the bass are messed up