Well, there are more than two. But this article hit on at least two of them:
In popular culture smoking a cigar is depicted as being an activity you engage in when you’re hugely successful or used to the idea of living an upscale lifestyle. It’s glamorized as being a very prestigious thing. Of course for the everyday person smoking cigars is simply about the joy and the flavour of it.
I would guess that for the wildly successful, the enjoyment of smoking cigars would be about the same (I'll tell you when I become wildly successful).
The quality of a good cigar is judged on two things. Number one, the quality of the tobacco inside the cigar. Secondly, the actual construction of the cigar.
Close, but no cigar. :)