Once mainly associated with portly, middle-aged men of a certain social standing, cigars – along with single malt whisky, fine wine, decent watches and interesting cars – have become part of the arsenal of interests that anyone who aspires to be a 21st century gentleman is almost required to hold dear. 

But the current enthusiasm for cigar smoking is merely the latest stage in a slow burn of popularity that can be traced back to the so-called ‘loadsamoney economy’ of the late 1980s, when flash city boys saw a top quality Cuban as just another hedonist’s accessory on which to splash a large amount of cash. Although that bubble inevitably burst, it remained airtight long enough for sufficient groups of truly serious enthusiasts to emerge, creating a ‘lifestyle’ around cigar smoking that American publisher Marvin R Shanken quickly addressed with the launch of luxury magazine ‘Cigar Aficionado’ in 1992. 

As the ’90s played out,  interest in cigars flat-lined – yet now cigars are hotter than ever. Why? According to George Frakes, vintage cigar consultant and historian at historic London retailer J.J. Fox, cigars, like so many other ‘hobbyist’ areas, have been given a turbo boost by the internet. “The availability of information combined with the fact that, since the turn of the millennium, Cuba has really brought cigar smoking into the modern age, has really helped, ” says Frakes. “Just as there has been a resurgence of interest in niche spirits, independent wine makers, specialist foods and so on, so smoking, discovering and learning about fine cigars has become a cool thing to do. They are very Instagram-worthy, and social media has enabled the worldwide cigar community to grow enormously because there is so much to talk about. Smoking a cigar is a very personal thing, as everyone’s palate is slightly different.” 

Frakes adds that the ‘ritual’ that is all part and parcel of the cigar hobby also adds to its appeal, along with the equipment and accessories that go with it. And, now that the so-called ‘New World’ producers such as Honduras, Nicaragua and the Dominican Republic have broadened the available selection beyond the products of Cuba and Jamaica, so there are more cigars to try, more to learn about and more information to share.
Indeed, fully ‘understanding’ cigars could be seen as a lifetime’s work – although anyone prepared to put the hours in could try for the gruelling Master of Havana Cigars qualification established by UK Cuban cigar distributor Hunters and Frankau, which culminates in an exam involving 200 questions spread across five categories. 

But if you’re a first-timer who simply wants to discover the almost inexplicable pleasure of a good cigar well smoked, Frakes wisely recommends a gentle start. “Go small, and go light,” he says. “I always suggest a Rafael Gonzalez Perla. It works every time…..” 

Here are some cigar enthusiasts to emulate, past and present – and their chosen smoke:

Sir Terence Conran, Doyen of design

After Sir Winston Churchill, Sir Terence, who died last year at the ripe old age of 88, was possibly the most famous British cigar smoker of the 20th century. He fired-up his first stogie, a Montecristo, to celebrate the opening of the Habitat store in 1964 – and never looked back. The Hoyo de Monterrey Epicure No2 became his favourite, and he is said to have smoked at least one per day for the best part of 55 years. 

Sir Terence Conran loved the Hoyo de Monterrey Epicure No2 (Getty)

Nick Foulkes. Journalist

‘Havana Man of the Year 2007’ and author of ‘Cigars: A Guide’, Nick Foulkes started smoking in his twenties. “I smoked my first cigar at the age of 26, a Monte Cristo No. 4 that was given to me by my father-in-law. It was the beginning of the ’90s, a decade that proved to be a boom period for cigars before they fell out of favour a bit shortly before the millennium, when it actually became quite difficult to find good ones in central London. But I continued to smoke, having fallen in love with the associated paraphernalia – lighters, cutters, ash trays, smoking jackets and so on – as well as the ritual and feeling of well-being. As a non-drinker, smoking cigars is the one thing I do that resembles manly behaviour and, I’m pleased to say, my eldest son, Max, has inherited my enthusiasm. He first visited Davidoff in St James’s when he was just six weeks old. Now he works there and, since the first lockdown, we have been making short films about our mutual love of cigars (Foulkes and Sons) which, to our amazement, have proved quite popular on You Tube and Instagram.” Favourite cigar: Cohiba Siglo VI. 

Sir Winston Churchill

The celebrated wartime leader took-up cigars in 1895 while briefly serving in Cuba and grew to favour La Aroma de Cuba and Romeo y Julieta cigars, the latter preferably seven inches long and of 47 ring gauge. He smoked up to 10 a day, often letting them burn without drawing on them, and is said to have kept a walk-in humidor at his Kent home, Chartwell, stocked with up to 4,000 smokes. He also had a favourite silver ashtray that would accompany him on his travels. 

Winston Churchill like to smoke La Aroma de Cuba and Romeo y Julieta (Image: Getty)

Peter Rosengard, founder of the Havana Room cigar club

Peter is an internationally renowned life insurance salesman; holder of a Guinness World Record for selling a $100m policy to David Geffen; founder of London’s Comedy Store and the short-lived ‘Havana Room’ cigar club. “I had never smoked anything until 1995, when I was 48 and my daughter, Lily, was born. We were booked-in for the birth at the Portland Hospital, where the service was so good that I stayed an extra three days. I had heard that the thing to do when your child was born was to smoke a cigar, so I went out and bought a box of Montecristo No 2, one of he world’s most popular types. 

“I didn’t find smoking them a pleasant experience at all, but then I discovered the Partagas Series D No 4 and fell in love. I have run my business from the same table at Claridges since 1981, always meeting clients there for breakfast. I would often enjoy a cigar afterwards but, when the ban on smoking in public places was introduced in 2007, I gave up cigars for good. After all, being a smoker causes one’s life insurance premium to double….” Favourite cigar: Partagas Series D No 4. 

Fidel Castro, late leader of the Cuban revolution, its prime minister and then president. 

One time king of cigar smokers, Castro was given his first cigar by his father at the age of 15 – and continued to smoke for 44 years, stopping shortly before his 60th birthday on health grounds. The only other time he gave up his beloved Cohibas Esplendidos – which were originally rolled especially for him before he made Cohiba into a ‘brand’ in 1966 – was while leading the revolution. An uprising of plantation peasants had given cigar smoking a bad image in Cuba. 

Fidel Castro (Getty)

Simon Khachadourian. Founder of the Pullman Gallery, St James’s

Specialist in the sale of vintage ‘objets de luxe’ – including luxury smoking accessories. “I smoked my first cigar at the age of 17. I had pinched it from my father to take to a party, where I confidently lit-up and promptly turned a very deep shade of green before failing to finish it. It was a Romeo y Julieta, fairly mild but still far too strong for a first smoke. After that, I didn’t touch a cigar again until I was in my 30s. This time someone taught me how to light it, how to smoke it without rushing and how to really savour it. It was a completely different experience and one that led to me really enjoy and appreciate cigars – but, at the time, I was a cigarette smoker. I was going through as many as 60 Gitanes International per day and realised I had to stop so I had acupuncture – and have never smoked a cigarette since. I do, however, enjoy Cohiba Club cigarillos during the day and, at home after dinner, I’ll often smoke a Cohiba Coronas Especiales. Favourite cigar. Cohiba Coronas Especiales. 

Groucho Marx, comedian and writer

Marx took-up cigars as a teenager while performing in Vaudeville, allegedly using cheap ones as props that, if he forgot his lines, he would light to fill time until the words came back. Later, a cigar became as much a part of Marx’s persona as his glasses, moustache and flamboyant outfits. He is said to have favoured La Preferencias because they were billed as offering ’30 minutes in Havana’. Although when his first lasted only 20 minutes, he demanded a replacement.

Ahmed Rahman, marketing director for an international apparel company

“My father smoked cigars regularly, and I always loved the aroma that wafted from his study. But I didn’t smoke one until after finishing my A’ levels, when three friends and I went for a celebratory dinner at the Goucho Grill. At the end , one of the others pulled out four tubes, each containing a Montecristo. It was an awful first experience – but, instead of deterring me, it spurred me on. I have smoked cigars ever since, and have a basic rule that I have one after every meal – breakfast, lunch and dinner. I may smoke more than that in a day, but rarely fewer. I like very strong cigars and, while I don’t think you can fault the Cuban brands for flavour, character and complexity, I believe many ‘new world’ cigars are better constructed. I’m not willing to name a particular cigar as my ‘favourite’ – instead, I would like to recommend newcomers to try a Trinidad Vigia.”

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