Classic Cocktail History: The Rusty Nail

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We've all got a favourite drink to order when we're under pressure at the bar. Having a go-to drink is a source of comfort in an outrageous world of fat-washed cocktails and pear infused espresso martinis. A go-to keeps you steady when you're overwhelmed by options.

Being comfortable is nice, but sometimes it's even nicer to throw caution to the wind and take a risk by trying something new. We say risk it, and risk it with The Rusty Nail. This classic Drambuie cocktail was the go-to drink of the Rat Pack boys (that's Sinatra, Dean Martin, Sammy Davis Jnr. and chums if you didn't know) in the '60s. It's a combo of Scotch whisky and spicy, syrupy Drambuie (which is made with herbs, honey and scotch) served with a twist of lemon.

The cocktail first appeared in 1937 at a British Industries Fair held in New York, and consisted of Drambuie, scotch whisky and bitters, uninspiringly dubbed the B.I.F. The cocktail then disappeared, but mysteriously popped up in the 1950s USA post-war boom. At the time, and for decades after, it was one of the hottest cocktails going around. The Rusty Nail as we know it today appeared under a variety of different names such as the Mig 21 (in Vietnam), and the D&S (in Manhattan).

There are several stories as to how the name 'Rusty Nail' came about. One story mentions rusted nails on the wooden cases of Drambuie that were dropped off in the Hudson and East Rivers in NYC during the Prohibition era, while another cites a bartender stirring the cocktail with a nail. It's most likely that the name has to do with the golden hue Drambuie gave to young Scotch whisky when it was mixed. All good stories, so we don't mind which one is true, and we've probably told all three as gospel after we've indulged in a few Rusty Nails.

The cocktail has been given the modern treatment by a fair few bartenders. It's not unheard of to mix Monkey Shoulder with Drambuie for an interesting flavour combination, or to mix tequila or mescal with your Drambuie for an extra kick. Drambuie is a top-notch way to pimp up your cocktails – you can skip using other syrups because the liqueur adds a splash of richness to your experience.

The story of Drambuie originates in 1740s Italy. A Scottish prince was sentenced to exile in Rome (doesn't sound too bad, really), and brought his personal recipe of mixing saffron and honey with Scottish whisky with him when he came back over to Scotland in an ill-fated attempt to reclaim the British throne for his father. Prince Charles Edward Stewart's name sits on the shoulders of the bottle as a reminder of how far this recipe has come.

Like a cocktail with a little bit of history? Suss out whether there's a bottle of Drambuie skulking around in your liquor cabinet. If there is, call your mates – it's Rusty Nail time.

Head down to A Night With the Nail at Sydney jazz club The Swinging Cat every Thursday for three months from September 7. It's your chance to try the Rusty Nail, and to see the bar decked out prohibition-style.