The classic cocktails are a lot of fun to make, but ordering them usually results in disaster. Unless it's a bar that cares about mixology history, you're likely to get something very strange. If it's purple and involves Sake and Chambord, don't call it a Martini. If you order a Sidecar and the bartender reaches for a can of Dr. Pepper, walk away.
The Rob Roy hails from New York in 1890, and is a variation on the popular Manhattan cocktail that was only 20 years old at the time. Whereas the Manhattan calls for rye whiskey or Bourbon, the Rob Roy incorporates Scotch as the primary spirit. The two drinks end up very different. A Manhattan is smooth and even a little sweet. A Rob Roy is bone dry and almost medicinal. The Scotch really amps up the aromas and flavors of the vermouths, and the whole thing just smells old, like opening up a chest that hasn't been touched in fifty years, or walking into a building that has lots of wood paneling, some cigarette smoke permanently bound to the walls, and the lingering presence of old products like St. John's Bay Rum aftershave or Vitalis hair tonic.
The Perfect Rob Roy Cocktail
1½ oz. Blended Scotch Whisky
¼ oz. White Vermouth
¼ oz. Red Vermouth
Dash of Angostura Bitters
Combine ingredients in a cocktail shaker with ice. Stir and strain into a cocktail glass and garnish with the cherry or a strip of lemon peel. I used Black Bottle Scotch for this--please don't use your good single malts. A blended whisky like Dewar's White Label is great for this drink (and appropriate, since the cocktail was pushed by the recent arrival of Dewar's in New York). This version is "perfect" because it incorporates both sweet red and dry white vermouth. The standard Rob Roy just uses red, a dry one just uses the white, but I think you get a more balanced beverage with both.
I'd suggest this one on its own for an afternoon cocktail or as an after dinner beverage. It's got such a strong flavor that you're likely to mess up your palate for food or wine during dinner.
Thanks to Bella who found the scent of the drink fascinating but was not permitted to sample it during her modeling duties.