I have been drinking Bourbon and smoking pipes for some two or more decades. May I suggest to my fellow pipe smokers or those interested in trying out smoking some pipe tobacco to give the following a shot.
I do not know why but the Corn Cob pipe seems to handle Burley type tobaccos the best and Burley type tobaccos seem to develop flavors in the Corn Cob pipe that do not come out in Briar pipes. Depending on the maker a wonderful nutty, chocolate, Café Cubano, creamy flavor comes from the combination. Please allow me to suggest a trio of Cob Pipes, Burley tobaccos and Bourbon to those who may be searching for the right pipe, tobacco and liquor to pair with each other. These suggestions are for products easily available in most of the USA or easily obtained via on line sources and the best part is that the prices are fantastically modest.
Pipes: Unless you own older cob pipes the only remaining maker in the USA is Missouri Meerschaum. These can be ordered from them for ,under $20. Most are under $10. I recommend their "General" pipe which is the medium sized pipe you see in the photo below of my arsenal of Cob pipes. I have a few older pipes from defunct firms that smoke just fine, but please be careful to choose MM made pipes as the ones made in China today are crap. Buying estate cobs is your choice but I almost always start out with a new fresh Cob and reject estate Cobs. I will smoke an estate Briar, Meerschaum, clay, etc but the old timers' cobs usually did not get cleaned right and were often smoked hard/hot so I usually pass on used or estate Cobs. I have found pipes will last me many years with proper cleaning, although I tend to make a purchase of a dozen or so, once a year to replace ones I have lost or broken. I will honestly admit that I do things to Cob pipes I do not do to more expensive Briar pipes. I bite their bits, I smoke them hard, I tend not to clean them that often, I jam them in my pocket, I leave them in cars, I travel with them. They are so modestly priced I feel justified in doing these things. Do not confuse cheap price with poor performance. Buy the Corn Cop pipe and you will not be displeased.
Tobaccos: So what to smoke in your Corn Cob pipe? I strongly suggest you try some Burley based tobaccos. I believe the products of Kentucky somehow work together on the palate in a wonderful way. Kentucky is famous for its superb quality Burley tobaccos. Call me crazy but I feel these tobaccos work so very well with Bourbon that I would be not surprised to find that the flavors were made, by the old boys, to work in conjunction with each other. This is good news for many folks, as these may well be the only pipe tobaccos available in your area. As well, these tend to be cheaper, over the counter type tobaccos. My favored brands for smoking in cobs are Walnut, Prince Albert, Edgeworth, Granger, Captain Black, Kentucky Club, Sugar Barrel, and a few others. Below is a photo of a stash I picked up from JRs this summer to give you an idea of tobaccos I tend to smoke with Bourbon. These may also work with some blended Scotches but tend to wash out some Single Malts.
Bourbons: As all here I have specific likes and very few dislikes when it comes to Bourbon. Below is a photo of some Bourbons that I have found work really well with the Cob pipe/Burley tobacco combination I am suggesting. Please excuse the mini-Rums in the foreground....how'd they get in there! I like the smoothness of Woodford Reserve, Eagle Rare and Maker's Mark as desert drinks with a good pipe. I also like the raspiness of Bulleit, Dickell, etc in the afternoon. Ryes work very well with the combinations I am suggesting too. Since I took this photo I have expanded my collection of Bourbons toward the lower and higher end brands. I have found the older bottling of Bourbons go very well with the tobaccos I have suggested. What you can expect to get out of these parings is an intensity of flavors in the Bourbon and Burley that may have laid in the background, being hard to perceive, in the past.