There are cocktails and there are classic cocktails. There are only a handful of drinks that have endured time, reconstruction, and parody to stand above the rest. In my opinion there are two cocktails that remain at the summit: the Martini and its great rival, the Manhattan. The origins of the Manhattan are a little mysterious. The popular view is that the drink was invented at the Manhattan Club in the late 1800s at a banquet hosted by Jennie Jerom, the grandmother of Winston Churchill. David Wondrich in his cocktail history ‘Imbibe’ provides a more appealing, yet imprecise view. Per William H. Mullhall, barman at the Hoffman House in New York City from 1882 to 1915, ‘the Manhattan was invented by a man named Black, who kept a place 10 doors below Houston St on Broadway in the sixties’. Who? Where? When? Fantastic. I’ll go with this delightfully ambiguous origin.
The Manhattan is unpretentious. It’s a simple drink to prepare, yet complex to savour. The backbones of the drink (spirit, fortified, bitter) provide infinite permutations and nuance. It’s a drink one can order in a dive bar in New York. It's a drink one can order in the Savoy in London or the Ritz in Paris with equal confidence. While a Martini signals (or possibly is intended to signal) elegance, class, precision, a Manhattan evokes a different, hi-lo proposition. Sophisticated perhaps. Louche maybe. Above all versatile. It serves well before dinner, but also as a post dinner sipper. Moreover, its rich, unctuous profile flavour can also provide a lovely counterpoint for a cigar. Here then are a few Manhattan options to consider (with a suggested cigar pairing).
Classic Manhattan
Simple as you like. 3 ingredients: bourbon, sweet (red) vermouth, bitters. Chill a cocktail glass on one side. Fill a mixing glass with ice. Add 2 measures of bourbon (Bulleit works well), 1 measure of sweet vermouth (Martini Rosso) and 3 dashes of Angostura bitters. Stir evenly until mixing glass is frosted. Strain into cocktail glass and add maraschino cherry. That’s it. However even this classic is subject to debate and internal preference.
Some purists prefer the drink to be less cloying, and substitute rye to bourbon. Some want more power in the drink, calling for a 3 to 1 whisky/vermouth mix. David Embury in his cocktail masterwork ‘The Fine Art of Mixing Drinks’ proposes a 5 to 1 mix. This is heroic and approach with caution. You can also play with the vermouth. If Martini Rossi is too sweet, consider Punt e Mes, an amaro from Turin. Using orange bitters instead of angostura bitters can provide more brightness and lift. My advice, start with the 2 to 1 bourbon Manhattan and iterate from there until you’ve found your preferred beverage.
Manhattan is a serious drink. Considerations on cigar pairing likely relate more to the timing of your drink. Pre-dinner, consider a smaller, medium strength cigar, for example a Montecristo Especial #2. Post-dinner, select a cigar with more heft and power. The Robusto vitola would pair nicely, say a Partagas D4 or a Ramon Allones Specially Selected. Your post dinner Manhattan has the backbone to stand up to these more full-blooded cigars.
Rob Roy
A Rob Roy is possibly the best known of the Manhattan variants where the underlying spirit is altered. The Rob Roy, which replaces bourbon with scotch, was invented in the early 1900s. According to Willliam Grimes in his work ‘Straight Up or On the Rocks’, the cocktail was named after a Broadway play that was popular at that time. It’s a charming drink. Add 2.5 parts blended Scotch (say J&B), 1 of sweet vermouth, 2 dashes of Peychaud’s bitters to a mixing glass filled with ice. Stir with enthusiasm. Pour into a chilled ‘Nick and Nora’ cocktail glass. Express the oil from a slice of lemon skin, then drop into the drink.
It's a lighter drink than the Manhattan. The peat and smoke of the Scotch whisky provides a little more lift and the spirit less viscous. The Peychaud’s bitters are more aromatic and sweeter than its Angostura counterpart. I would recommend this as a pre-dinner aperitif. It would pair nicely with a lighter profile cigar, say for example a Fonseca Cosaco. The Fonseca’s attractive presentation and dimensions (135mm by 42 ring gauge) might serve very well with the Rob Roy before dinner.
