Not a particularly frequent poster here, but thought I'd share a good mating with you cigar fans.
Many cigars do not have enough body to stand up to a high-proofed beverage and retain all of their character. Those that do, are exceptional sticks deserving a great bourbon pairing. Provided you do not need to do any driving or operate any heavy equipment afterward, I have an excellent pairing for you provided you can get around the Trading with the Enemy act. A neat Knob Creek and a Montecristo No.5. Not an all evening affair with the tres petit corona-sized Monte No.5, but a pleasant 25 minutes, just perfect for a nice pour. Don't let the small size of the No.5 prejudice you against this cigar. As with many small ringed Cubans, this packs quite a wallop. Very straight-forward peppery cigar that has no subtleties to be covered up, it shines through the sweetness (to my palate) of the Knob Creek. Unlike some of the more highly desired Cuban models, the No.5 can be had for around the $4 or $5 mark provided you can find them.
However, if you're looking for a good afternoon pairing for under $2 for the pour and the cigar, you can't beat a Jim Beam and a Consuegra #7 (Consuegra is the factory second to the Villazon factory in Honduras, for brands such as El Rey del Mundo, Punch, Belinda, and JR Ultimates) corona in maduro. Great living at a low price.
Life's too short for bad music!!