Last night I was able to mellow out with a Don Bienve 1981 Limited Reserve. Very impressed with it. Not as mild as I had expected (very nice pre-light smell too) and it generated a decent amount of smoke. Really rolled over my tongue and exhaling through the nose definitely brought out more character. Once my palate is more developed, I'm sure I'd be able to describe it better. All I know is that it was a good smoke.
Started off with a Penn Dark beer and it matched very well - I love how a good beer can enhance a good cigar and I really noticed how the cigar made the beer taste different as well - masked the bitterness and enhanced the sweetness.
Halfway through I switched to an A&W Root Beer - also very good, but I think I prefer the regular beer. The root beer was already very sweet and the cigar seemed to make it a bit too sweet. But that may just be me...