John Hodgman. I know the 10 Ferret Night episode didn't really focus that much on tech news but I laughed my tail off all the way home.
Source(s):
Here's the link to the episode:
http://twit.tv/174

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I really liked LeVar Burton on the latest episode. But I'd have to say my favorite is #174, 10 Ferret Night, with John Hodgman and Jonathan Coulton, Hodgman being my favorite guest.
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Dare I say... Jason Calicanis? (Do I get a big M$ tip if I do?)

I used to like Merlin Mann, but he was getting to much into the sarcasm/rat hole hole for me. Right now, I can only handle small doses of Mr. Mann. But, don't get me wrong, I LOVE his humor.

That leaves me with... Jason Calicanis. No... really. Jason keeps the subject on tech topics and has some REALLY good questions about those topics. And, if he doesn't know, he's humble about it.
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I'd have to say Dvorak. He's the perfect (and necessary) balance to Leo's personality.
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John Dvorak is the best guest! His does not hold anything back and his blunt comments are needed when the show jumps off track.
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I was a guest 2 or 3 times, so I'll say myself :)
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John C. Dvorack and Jason Calicanis, they both are highly charged with good insight. They both offer balance and contrast to Leo. Oh and Ryan Block.
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