Review:

Scotch whisky's answer to the Manhattan. The Rob Roy is classically made with Angostura Bitters, but in his 1948 The Fine Art of Mixing Drinks, as a footnote below his recipe, David Embury attests "Peychaud, somehow, seems to blend better than Angostura with Scotch."

I find Abbott's Bitters combines more harmoniously with the whisky in this cocktail. Or if not to hand, I use one dash Angostura-style aromatic bitters and one dash Peychaud's/creole bitters. Whatever bitters you use, their inclusion is essential to the balance and complexity of this cocktail.

Variant:

Made with orange bitters this becomes a Highland or Highlander cocktail.
White Rob Roy

History:

Named after the Rob Roy operetta about the Scottish folk hero and outlaw Robert Roy MacGregor, which debuted on Broadway near where New York's Waldorf Astoria Hotel used to stand. (The Empire State Building occupies the site today.) Hence, it's not a stretch to believe this cocktail was created at the hotel to serve operagoers and that scotch whisky was appropriately swapped for the usual American whisky in the popular cocktail of the day, a Manhattan.

The New York Times 30th October 1894 review said "the latest work of Harry B. Smith and Reginald De Koven" was "clean, frank, manly, bright, and winesome." The same words could have been used to describe the cocktail, and before David Wondrich uncovered more about this cocktail, then the above was a neat, concise origin story.

It turns out there was a Rob Roy cocktail created some 20 years earlier by New York bartender Edward F. Barry, and this is documented in an interview he gave for the New York Sun 22nd August 1873. "The Rob Roy cocktail is made with a little gum syrup, two dashes of Angostura, a few drops of oychette cordial [orgeat], in a tumbler filled with fine ice, strained." - New York Sun. Sadly, the interview doesn't record what the base spirit was. This earliest known reference is just the first not to confirm or even cast doubt as to the original base spirit in a Rob Roy.

It's worth noting that the first recipe for a scotch whisky-based Manhattan, which appears in Charlie Paul's American and other Drinks, published 1884 in London, bares no reference to the cocktail also being known as a Rob Roy.

MANHATTAN COCKTAIL.
Fill tumbler with chipped ice; put in three or four drops of angostura bitters, ditto of plain syrup; and half a liqueur glassful of vermouth, half wine glassful of scotch whiskey; stir well with spoon and put a small piece of lemon on top.

Charlie Paul, 1884

The earliest Rob Roy recipe based on scotch whiskey that I've found appears in James C. Maloney's 1900 The 20th Century Guide For Mixing Fancy Drinks (published in Chicago, USA), but with lemon juice and other estranged ingredients it is far from the modern-day scotch whiskey-based Sweet Manhattan.

ROB ROY COCKTAIL.
Fill mixing glass two-thirds full fine ice.
¼ teaspoon of lemon juice.
1 teaspoon of syrup.
2 dashes of orange bitters.
1 dash Peychaud's bitters.
12-3 wine glass Scotch whisky.
1-3 wine glass French Vermouth.
Stir well and strain into cocktail glass and serve.

The Cocktail Book a Sideboard Manual for Gentlemen, 1901

Just a year after that recipe, another Rob Roy, based on scotch whisky and a Manhattan with orange bitters, appears in the anonymously written 1901 The Cocktail Book a Sideboard Manual for Gentlemen published in Boston, Massachusetts, USA.

Rob Roy Cocktail.
Use Mixing Glass.
Two dashes orange bitters; two-thirds Scotch whiskey; one-third Italian vermouth. Fill with ice, mix, and strain into a cocktail glass. Serve an olive in the glass.

The Cocktail Book a Sideboard Manual for Gentlemen, 1901

The 1909 edition of the same book (published in London, England) gives an updated recipe which calls for Angostura bitters in place of orange bitters. The only thing in this 1909 recipe that differs from modern renditions is the olive garnish rather than the modern preference for a cherry.

Rob Roy Cocktail.
Use Mixing Glass.
THREE dashes Angostura bitters; two-thirds Scotch whiskey; one-third Italian vermouth. Fill with ice, mix, and strain into a cocktail glass. Serve an olive in the glass.

The Cocktail Book a Sideboard Manual for Gentlemen, 1909

In Paul E. Lowe's 1909 Drinks : How To Mix And How To Serve (published in London, England) the base spirit question is once again raised by his stipulating apple brandy.

Rob Roy Cocktail
2 dashes gum syrup.
½ jigger apple brandy.
½ jigger Vermouth.
Stir; strain into cocktail glass and serve.

Paul E. Lowe, 1909

Also uncovered by David Wondrich, in a 24th March 1941 edition of the New York Sun, is a letter to G. Selmer Fougner's Along The Wine Trail column. The writer is the brother of Henry August Orphal, a bartender at the Duke's House in New Jersey. The letter describes how his brother was put on the spot by a representative of Usher's to create a cocktail using his blended scotch whisky. Appreciative of the new cocktail, the salesman named it the Rob Roy.

To conclude, a version of a cocktail named Rob Rob appeared before 1873 and took its name from the 1817 historical novel by Walter Scott rather than the operetta based on that novel, which didn't premiere until 1894. The popularity of the operetta in New York must have helped to promote Rob Roy as a cocktail name.

Scotch whisky-based Manhattans were being made before 1884, but they were as likely as not, or even more likely, to be called Manhattans.

The first recipe for a scotch whisky-based Rob Roy appeared in 1900 but is far from being the Manhattan-style cocktail we know today. The first recipe for such a Rob Roy appeared a year later in the 1901 The Cocktail Book a Sideboard Manual for Gentleman.

Also see: Manhattan cocktail history

Nutrition:

One serving of Rob Roy Cocktail contains 179 calories