I don't like to drink anything when I smoke a cigar, I tend to concentrate on the cigar itself. I usually wait until I have time to fully relax and immerse myself in a cigar, rather than smoke while I do other things. Maybe one day I'll get a little more into wine, like I'd like to do...maybe then I'll try to pair wine with cigars. For right now, I really enjoy a cigar by itself. I guess I'm in the minority on that one.
Cigars deserve their own space, when they're good, but even loners enjoy a bit of company now and then. Dark beers do nicely, if you like them, with a hearty smoke, as they harbor a subtle sweetness.
But the ultimate classic complement to a good cigar is a nice glass of port. FICKLIN'S California port won't let you down, nor will myriad Portuguese editions. Easily acquired are: WARRE'S Warrior; COCKBURN'S (Pronounced CO-BURNS -- there may be ladies present); SANDEMAN; DOW'S; FONSECA (Yes, like the cigar -- I don't KNOW if they're related, but I suspect so)... The list goes on and on. "Tawny" or "Ruby" (these are basically color designations) and 10 year old offerings are very nice, while 20 year old (and older) are even nicer, but tend to be pricey. "Vintage Character" ports, like Warre's Warrior for instance, are good values and will get you there comfortably.
My experience with spirits, i.e., Cognac, Bourbon, Scotch, etc. is that they usually overwhelm the palate leaving it numb and dry, tending to kill the taste of your cigar. Port, on the other hand, soothes the palate and leaves a slight sweetness, which will complement and round out the flavors of most good cigars.
Dry red wine, stick with a steak. Dry white, filet of sole, get the idea?
IMHO
Sorry to be so wordy, but take heed. I do know whereof I speak. :yes: