I prefer to write about boxing matches but a good down and dirty fight works occasionally. This had to be the funniest show that I have ever seen Letterman do. Normally, I just don't think he's that funny.
8:47 minutes of pure terror for Ms. Hilton is how I would sum it up. It starts out with the common greetings and Letterman taking a good stare at Hilton's legs. You can then begin to hear it in his voice, Letterman is setting her up: "How have you been - all right?" Of course he says this in his little creepy voice, not to mention that you can tell he's up to something. He gets right to it and asks: "How'd you like being in jail?" It never gets better from Ms. Hilton's viewpoint!
Letterman even asks her if she knew what she did to go to jail. She avoids answering. It's about at this point where you can tell that she is starting to feel the heat. This is where the dirty looks start as well.
"Have your friends treated you differently since you've been out of the slammer?" Oh, this is good stuff. Letterman just keeps coming and coming. At one point Hilton gets really upset and has this, I'm about to cry look. This is where she starts bouncing around in the seat.
I'll stop there and not ruin it for you (assuming that you haven't seen this masterpiece).
Check it out! This is my all time Letterman favorite.
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