The most expensive cigar I've ever had was the Zino Platinum Crown line. They run from $35-$42 apiece, but after smoking a few, they are well worth it. It's almost like realizing that no cigar you've ever had can measure up to this beauty.

They smoke perfectly, and have not a hint of bitterness or harshness. Very smooth, but full of flavor, and they shift on you at least twice. That's the effect you get from lovingly cared for, 5+year aged tobacco. I buy them about once a month, that's all I can afford, but I would smoke them a lot more often if I could afford more.