Enjoying a glass of bourbon while smoking a cigar seems like an average Friday night to some people. However, pairing a bourbon and cigar can be more complicated than you think. We sit down with Jake Glancy and Jeremy Kendrick of Jake's Cigar Bar to get a complete cigar 101 lesson on everything from cuts, types, leaf varieties, and more to understand how the unique flavor of a cigar will compliment different types of bourbon. You will want to rush outside and smoke a cigar after listening to this one! Show Notes: Let's start from the beginning and talk about the types of cuts How do you pick the ring gauge or size of cigars? Talk about the wrappers and what flavors each type release What's the difference between tobacco in Nicaragua and Honduras versus in Kentucky? Talk about hand-rolled versus machine-rolled. Bourbon drinkers have a progression from mixing to neat, what about cigar smokers? What do you mean by tasting a cigar by "thirds"? It's moving from cigars and scotch to cigars and bourbon. What's the initiative? Describe the different shapes of cigars When you're smoking a cigar do your taste buds or receptors change rather than drinking bourbon alone? What's the sweet spot for the third in your opinion? I'm going to throw some bourbons at you and you tell me what cigars would pair well. Talk about higher in proof bourbons like Stagg Jr and barrel proof bourbons and the cigars that pair well It seems like Four Roses pairs well with any cigar Talk about barrel aged cigars What about something super light like 80 proof Basil Hayden Rye whiskey is growing in popularity. How does rye whiskey stand up in cigar pairing? How about something that's super oaky like Elijah Craig 23? How about finished bourbons like Angel's Envy port finished bourbon? The craft market is booming but what do you pair with something that has a grain forward flavor? Talk about the Van Winkle Cigars. Are they good or are they hype? I see a lot more Barrel aged cigars on the market and I am curious for recommendations and also some info on the technique and how it imparts the flavor from the barrel to the tobacco. Are Cubans really that much better? Get 15% off at Jake's by mentioning you heard about them on Bourbon Pursuit! Learn more about your ad choices. Visit megaphone.fm/adchoices