>>6902405Macanudo is, I think, the most popular brand in the US, and it's great, if a bit pricey. I'm speaking in terms of a regularly enjoyed cigar; there are assuredly more expensive and higher quality ones, but they're not the type you smoke willy-nilly after a day at the office.
Macanudo as a general brand is good. Drew Estate is perhaps my favorite, they have a wide array of smokes that I really enjoy. Swamp Thang cigarillos are probably my favorite for a daily smoke. Sweet Janes are one of my all time favorite by them, both cigar and cigarillo. Macanudo Cafes (technically ascots, not cigarillos) are phenomenal in the morning with a cup of coffee.
If you're just getting into smokes, I would urge you to find a legitimate cigar lounge nearby and strike it up with the person working there. If you've never smoked cigars regularly - I don't mean at a wedding or some shit - then go real easy. You want something mellow, probably not with a lot of spice. Also I drink a soda or some kind of sweet tea when I smoke, like Dr Pepper, if I'm not having coffee. It's best to have some kind of cold drink. I would absolutely NOT start out with whiskey or any type of liquor your first time; it can be a surprisingly potent combination and really fuck up your stomach. Don't be surprised if you feel like you have to shit real bad the first time you smoke.
There's an absurd amount of cigars out there to try, though. All kinds of websites and apps and shit, it's a huge culture. Take your time and enjoy yourself.