David Letterman grilling Paris Hilton

This is actually kind of sad. I almost want to feel bad for her and than I realize she's had it so easy with all the mistakes she's made that she sort of deserved it.

 She had to expect something like that. I mean, it's the Dave Letterman Show for pete's sake.

Letterman was funny, but Hilton didn't deliver anything funny (I don't think she's smart enough to crack a decent joke).  She's not wearing a bra because...well (there's no politically correct way to say this), she isn't that well-endowed up there, and probably doesn't need one. 

More funny!  You can't go to jail as a celebrity and not expect to be drilled for it.  Should of thought of that beforehand.....Dave's hilarious!

This girl, like her or not, made herself into a celebrity by the power of gossip, media, and money. This managed to get her a TV show, an album and a lot more money and fame.

David Letterman made himself into a respectable TV persona by being sort of rude and harsh on his guests, this approach made the show very long running, successful and economically satisfing, for him and the TV channel he works for.

Personally, I don't find it sad or funny, I don't care about the lives of those people at all, and so if she's being humiliated or taking part in this joke - I don't really care.

The both win, both on the fame angle and the money angle. The one who looses from this is the audience who get to waste time, money and brain cells on celebrities...