I find that joke funny now but I suppose it is all to do with familiarity. Yes that is funny the dollar bill nickname joke I bet Lynne will take stick for that in private especially as she laughed so much at it.
The horse/cow joke is similar to ones I hear all the time dad had a stunt pulled on him years ago when he was an insurance agent and visited a farm they got him to go and see a "cow" and told him to feel the cow in a certain area because it was a cow with mastitus (I know I have spelt that wrong but the spell checker not co-operating) but then when the "cow" turned round it had a ring in its nose it was a bull. So I suppose her joke with the horse had a familar ring to it for me.
And the teasing ones of George re Desperate Housewives were both on a topical subject and one could see how he was enjoying her teasing him.
I think the Chippendale joke probably had it been 15 years ago when they were at their height would have just washed over me because at that time there were lots of Chippendale jokes. I think when things are topical and familar you react differently.
I said this on another thread about the dinner that turned into a thread about funny things our moms, dads, grandmas and grandpas have said, but here goes re the Chippendales.
When I was getting married, my so-called "bachlorette" party that included me, my best friend and my two sisters, and lots of Pepsi and potato chips (bo-ring, to be sure, but we had fun) was of course planned for the night before. My mom asked me if we were going to have the "Clydesdales" come to entertain us. Of course, she meant the Chippendales, but I sure got a kick out of her question!