Tony Katz and Fingers Malloy light up the Dunbarton Tobacco & Trust Year of the Duque and immediately get stuck on the most important question of all: how exactly do you pronounce it? Along the way, they break down the cigar’s rich, low-maintenance smoking experience, talk through notes of wood, char, cocoa, and spice, and debate whether a 5x48 stick at nearly eighteen bucks earns a place in the humidor.

On the drink side, they crack open Jack Daniel’s Sinatra Select and ask the big question: Is the presentation, the pedigree, and the price tag worth it? There’s plenty of talk about banana on the nose, cherry, brown sugar, oak, and whether this Tennessee whiskey is a true splurge bottle or just a handsome box with a famous name on it.

Also in the mix: birthday freebies at chain restaurants, the madness of modern tipping culture, mystery hotel fees, sleep advice from the internet, Fingers’ mullet era, and the kind of lounge conversation that somehow goes from cigars and whiskey to transcendental meditation and international politics without ever losing the thread.

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