Rusty Nail

Scotch and Drambuie — the heather-honey Scotch liqueur produced in Edinburgh from around 1910, popularized in the 1950s–60s by the Rat Pack.

The Rusty Nail pairs Scotch whisky with Drambuie — the Scotch whisky-based liqueur flavored with heather honey, herbs, and spices whose commercial production the Mackinnon family began selling in Edinburgh around 1910. The Mackinnon family's promotional narrative holds that the liqueur recipe was given to their ancestor John Mackinnon by Bonnie Prince Charles Edward Stuart following the catastrophic Jacobite defeat at the Battle of Culloden on April 16, 1746, as a gesture of gratitude for sheltering him in the retreat across the Hebrides; cocktail and spirits historians treat this origin story as unverifiable romantic legend rather than documented history, as no contemporary evidence supports it. What is documented is Drambuie's commercial development in Edinburgh by Malcolm Mackinnon from 1910 onward. The Rusty Nail's commercial popularity peaked through the 1950s and 1960s when it became associated with the Rat Pack — the informal group of entertainers including Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop — who were reported to favor the combination. The drink's name's origin is uncertain; one account attributes it to an obscure competition during which a bartender called it a rusty nail, though no single origin is documented.