Whiskey - no question, W.L. Weller Special Reserve (bourbon). White label, seven years old. Better than Jack black label, Maker's Mark, any of them. Either straight with ice, or caffeine-free coke. That's great stuff, but couldn't find it up north (Michigan) a few years ago when I went up for a niece's wedding. Don't know if it's available in TX or not, but if you can get it, it's the best bourbon I've ever found. They make a 12-year old silver-label version, but I almost never buy it; the 7-year is that good.
One of my favorite topics is discussing drinking with someone from church; as they've usually got a reflexive aversion to it. I ask them if they think it's ok to occasionally take nyquil to get to sleep, and they of course say 'yes'. The next obvious comment is that bourbon is at least 'mostly' natural, not concocted up in some 3M or Phillips Petroleum laboratory. Obviously, getting drunk is a different topic, but if I can get the same somnificant effect that nyquil has, using bourbon, it seems like "poor stewardship" to use the Nyquil. After all, the bourbon is more natural, cheaper, and has much fewer harmful chemicals in it; that's objective fact. (Yes, I'm obstinate sometimes...)
Cigars - nothing fancy. Usually mail-order Thompson's house-brand "hand-made Dominican". I buy the 5x50 size (robusto?), usually work out to just over a dollar a cigar in bundles. I've tried quite a few different ones bought individually, (including a few Cubans when on a cruise once; they were noticeably stronger, yet very good), but I'm apparently not sophisticated enough for one to just "grab" me, so I largely stick with the mail-order Thompsons. I can accept that I'm somewhat "low-brow"...
I prefer the taste and smell of a pipe, but not the hassle involved, so the pipe (I have two) is rarely smoked. When I do, it's usually "Smoker's Pride Whiskey Blend" tobacco. That stuff just smells great. (Of course my wife doesn't think so, so out of consideration for her & the kids, I don't smoke in the house or the vehicles.)