The most entertaining things about Season 3 of Supernatural...
...is watching Ruby kick the crap out of Dean for about a minute and a half.
I have to say, for all the season's problems, I think the worst is the way she spent the entire season saving and helping them and he constantly called her a bitch, and eventually added slut to it. And he was doing this while she was saving his life, and even when she was ready to kill herself to save them.
Incidentally, regarding Gordon and Hendrickson: I think they redeemed themselves regarding Hendrickson in Jus In Bello (though Dean's horror at the idea of a pretty adult woman being a virgin and his "sweet young thing who ain't even been laid" killed my good will there), I think they dug the grave even deeper with Gordon.