It must be a pretty depressing time for your average movie mogul or bank president. Despite the fact that business in general appears to be doing well the world over (give or take the odd country), they have managed, inadvertently, to lose control of that most potent symbol of rampant capitalism, the cigar. A decade ago it was the preserve of the great, the good and the downright disgustingly wealthy. Fat cats in pinstripes could be seen chomping down on their huge stogies, content that they were, literally, chewing on the butt of a Communist country. Ten years on, and not even Castro could have dreamed of such a widespread appreciation of his most endearing habit. And how has this come to pass? It’s the fickle hand of fashion yet again. Spurred on by supermodels such as Kate and Naomi – who have appeared, robusto in hand, their faces ringed in a haze of blue smoke – cigars have become the latest thing. To add fuel to the fire, we are increasingly encouraged by an ever-growing number of bars and restaurants to indulge in our filthy habit. Delightful. Fidel, and countless of his ex-countrymen in Miami and the Dominican Republic, must be laughing their heads off. The problem with cigars, however, especially if you are a relative newcomer to this thoroughly anti-social habit, is where do you start? Like wine or whisky, there is a staggering choice available, and it gets bigger every day. Do you, for instance, go for Cuban (expensive but great quality)? Do you opt for the less purist option, the Dominican Republic (more affordable) or Honduras (increasingly better quality)? Or do you go for Jamaica, Mexico or even Nicaragua? And then of course there is the question of size. This matters, though not necessarily in terms of bigger is better. Finally, and this, like whisky, is where the great enjoyment comes in, there is the question of style and flavour. Each cigar has its own distinctive style and each has its own unique combination of flavours. The latter is particularly appropriate when you are trying to judge what to smoke, when to smoke it and with what. For example, the Bolivar Corona Gigantes is one of my personal favourites, but if I wanted an early evening smoke with a nice light dram it wouldn’t be the one for me, for a variety of reasons. First and foremost, the Corona Gigantes is, as its name suggests, a bit of a whopper: seven inches to be precise. By the time I’d managed to work my way through it, it would be nine o’clock, I’d have missed my supper and would probably be slumped in the corner, pickled. Second, it’s also one of the most intensely flavoured of Cuban cigars, demanding serious concentration and a strong constitution. Third, for exactly the same reason, it would overpower – some might say annihilate – the flavour of the whisky, which sort of defeats the overall intention, which was to enjoy the two together. So what are the guidelines, if any, for choosing the right cigar and, if the mood takes you, matching it with the right whisky? Well the first thing to do is cut down your options. Your wallet may well disagree, but your tastebuds will certainly thank me for it when I say stick to Cubans. Why? Well, Cuban cigars – when bought from a reputable retailer and stored correctly – are, quite simply, the best. Other countries, most notably Honduras and the Dominican Republic, make some superb cigars, but in terms of quality and complexity Cuba nearly always has the edge. Now, Cuba alone produces some 35 different brands of cigars, the most famous of which is probably Monte Cristo, and within each brand will be a number of different sizes. The world’s most popular Cuban cigar, for example, is the Monte Cristo No. 4, but there is also a Monte Cristo Churchill, Monte Cristo No. 1, No. 2, No. 3, Monte Cristo Pyramid – the list goes on. It’s the same for Cohiba, Romeo y Julieta, Hoyo de Monterey, Partagas and so on. The thing to do is choose the size that fits best. For early evening something like a petit corona (five inches) or a robusto (five and a half inches) is best, purely from the time element. A cigar takes time to smoke properly and there’s no point in hurrying it. For the end of the evening the sky is pretty much the limit, but something like a double corona is going to take you a good hour and a half - maybe longer - to smoke, so make sure you’ve got time. A panatela (thinner and about an inch shorter) or a lonsdale is much more manageable. In terms of style it obviously depends on personal taste. If you prefer a medium-to-light cigar, something smooth but with complexity, you could opt for something like a Monte Cristo (No. 4 or No. 3) or a perhaps a Romeo y Julieta Vintage No. 1. The latter is quite creamy and spicy but not too overpowering, whilst the former displays all that Monte Cristo has become famous for, a very smooth, almost sweet smoke with a nice nutty, herbal character. For something a little heavier, you need to move on to the likes of Bolivar, Cohiba or Hoyo de Monterey, where the richness of flavour is more intense and you get much greater spice, nut and cedarwood characteristics. The important thing is to experiment, gauge what your personal style is and, most importantly, don’t be afraid to ask the advice of a specialist – it’s their job. So far, so good. But it’s when it comes to matching cigars with drinks that things get more complicated. The classic cigar drink is often thought to be Cognac, with the odd nod towards vintage port. However, most cigar lovers quite openly profess that whisky is about the best match you can get. There is something about the smoky, peat-laden flavours of fine single malt that marries particularly well with cigars. One of the most important things to remember about cigars is that they dry the mouth. With this in mind it’s nearly always best to choose a whisky (or whiskey) that has a touch of sweetness to it. Single malts, for instance, that have been aged in sherry or port casks have that edge of sweetness that helps cut through the drying flavours of the cigar. Likewise with bourbon, whose sweeter nature often makes it ideal with a good cigar. It’s also worth bearing in mind that most crucial of elements in good malt whisky – peat. Malts like Ardbeg, Lagavulin or Laphroaig are a good match with some of the richer, nuttier, more highly spiced styles of cigar, like the Bolivar and Hoyo de Monterey. By contrast, lighter whiskies, like Aberlour, Glenfarclas or Cragganmore, go better with medium-bodied cigars, perhaps a Romeo y Julieta Cedaros. Likewise, there can be a regional distinction. Many Islay whiskies, such as Bowmore 17-Year-Old or Ardbeg 17-Year-Old, have slight orange peel and marmalade notes to them as well as flavours of cigar box and vanilla. These would both go quite well with something like a Hoyo de Monterey Epicure No. 2, which has notes of cedar and quite heavy spice that would marry well with the orange peel flavours. Similarly a whisky from the Campbeltown area, such as Springbank or Glenkinchie Amontillado Finish, would suit a medium- to full-bodied cigar. By contrast the lighter, more floral notes found in many whiskies from the Central Highlands – Glengoyne or Dalwhinnie 15-Year-Old – would be better suited to a medium-bodied cigar that has less spice and a little more nuttiness. In the end, of course, it’s all personal choice. And you don’t even have to be a fat cat.