Cigar smoking is a culture in itself, and in order to appear Cary Grant-like, you must know how to cut a cigar, light it and finally, smoke it.
Ask the salesperson whether the cigar consists of 100% tobacco -- that's what you want.
Although cigars are broken down into groups, depending on where they're made and the tobacco leaves used, here are several categories of cigars classified by their shape and size.
Churchill
Measures 7 inches by 47-ring gauge (refers to the measurement for the diameter of a cigar). Named after Winston Churchill himself, who made the cigar one of his trademarks.
Corona (not the beer)
Measures 6 inches by 42-ring gauge. The standard by which other cigars are manufactured, the corona has an open foot (the end you light) and a closed head (the end you smoke), which is usually rounded.
Pyramid
Has a pointed, closed head.
Robusto
5 inches by 50-ring gauge.
Torpedo
Has a pointed head, closed foot and a bulge in the middle.
Panatelas
At 7 inches by 38-ring gauge, these are usually longer and thinner than coronas.
Culebras
Three Panatelas braided together to form one cigar.
Diademas
8 inches or longer, this large cigar usually has an open foot.
Perfecto
Similar to the torpedo, except that it has two closed ends with a bulge in the middle. A rounder cigar.
Now, let's move on to the most effective way to cut the cigar....
Aim of cutting the cap on the head of the cigar: To create enough of an opening to smoke the cigar comfortably, while maintaining the original shape of the cigar.
So how is this done? No, biting the cigar is not a cutting method. Not only is this ineffective since your teeth are not real cutting tools, but you will look nothing like an aficionado while you're spitting out the leftover tobacco in your mouth.
Straight cut (most recommended): Use a single-bladed cutter to horizontally slice off the head in one quick "chop" (a la guillotine). With this single, swift motion, you lessen the probability of tearing the cigar's wrapper.
Before cutting, bring the blade down towards the cigar -- just enough to tap the cigar -- to ensure that your blade is positioned properly and aiming at the right spot on the cigar. The bull's eye is right where the cap of the cigar meets the wrapper, leaving sufficient space to ensure that enough of the cap is left surrounding the wrapper, preventing it from falling off.
With a double-bladed cutter, chances of making a clean cut are increased and you're less likely to tear the wrapper with the blade, since the cigar is being cut from both sides simultaneously.
One reader suggested cutting the cigar by laying the cutter flat on the table, and then placing the cigar flush against the table, through the cutter.
Now that you've come this far after choosing your cigar and cutting it to perfection, you don't want to mess up all that work or tarnish your image by lighting the cigar the wrong way. It's best to light a cigar with a cigar lighter, as the ammonia from matches may spread to the cigar and alter its smell and taste.
You're better off not using matches, a cigarette lighter, and especially not a candle.
If you must use matches:
Use longer ones; short ones make it hard to light a cigar, especially on the first couple of attempts. Try to find matches without sulfur and if you can't, at least wait until the sulfur burns away.
Proper etiquette calls for removing the band at some point whilst smoking the cigar. The reason you need to keep it there before smoking it is to prevent the tobacco from tearing, but once the cigar's lit, you don't need the band anymore.
Enjoy and savor the stogie, but do not inhale! After 12 puffs or so, remove the band, which will probably be falling off on its own thanks to the heat.
So sit back with your cigar in one hand and a glass of port, cognac, bourbon/scotch, or wine (preferably Cabarnet Sauvignon or Mourvedre) in the other. Before you know it, you'll be discussing humidors and habanos all night long.