I'd agree with Kuzi - go to http://www.cigar.com and look around a bit. Then call them (800.357.9800) and talk to them. The guys on the phone really know cigars and can help you put together the perfect gift.
Or, you could take that $100 and buy a few months subscription to the cigar-of-the-month club. That way he'll get the cigars spread out over a few months and he'll be assured to get some excellent cigars with a nice variety.