I'll try just about anything as long as it seems like a good smoke that'll go with a bourbon on the rocks. I usually smoke CAOs, Padrons, Monte Cristos, Rocky Patel, etc. I usually keep a bunch of Punch cigars as an "every day smoke" but I need to get some more of them - they are a decent cigar for only $4-5 and I don't mind giving them to friends like I would a $12-15 cigar.
I've always been weary bought cigars online, so I've always bought local. However, Macanudo is selling there new line of premium cigars online for 9.95 shipped for three, so I bought some to see what buying online is all about. I'll have to check out cigars.com
EDIT: Right now I am smoking one of these in a torpedo:
http://www.torano.com/cigar_detail.asp?CatID=15 with a glass of Evan Williams.