Historically, scotch and whiskey cocktails are an American invention. In Europe, traditionally, most spirits are drunk with a little water or straight up. The tradition of mixed drinks started with American pharmacists who began mixing a brew of alcohol with carbonated drinks and syrups to make medicine taste better. The idea caught on and bartenders started mixing spirits with carbonated drinks and juices for their clientele. The cocktail culture took off in 1806 when a New York newspaper reported mixed drinks for the first time! According to the New York Times, the first cocktail recipe book was published in 1862 and authored by Jerry Thomas. It was called The Bartender's Guide: How to Mix Drinks: A Bon Vivant's Companion. Bartenders tried all manner of mixtures to determine what creations the public would drink, and some of these cocktails are still popular today like the Rob Roy.

According to Drink Magazine, after a keg of Dewar's was delivered to the White House in 1891, Americans' demand for authentic Scotch increased. There was a rush to import more of this amber Scottish liquor despite protests from U.S. distilleries. This is around the time when the newly created Rob Roy cocktail was created by replacing bourbon or rye with scotch.

One of the ways to stay ahead of the pack as a hotelier and restaurateur in NYC in the 1890s was to create a new cocktail sensation and name it after a popular production to draw clients in the door. That said, most folks believe that the birthplace of the Rob Roy cocktail was at New York City's infamous Waldorf Astoria in 1894. At that time, the Waldorf was located where the Empire State Building now stands. Just down the block from the Waldorf, The Herald Square Theater, was producing Reginald De Koven's operetta called "Rob Roy," based on the life of the Scottish folk hero. The bartender at the Waldorf decided to create a new drink, the Rob Roy, to promote the hotel and the opening of this performance. Similar to a Manhattan, the bartender prepared his new Rob Roy creation with scotch instead of rye whiskey. It was a sensation and became popular across the country.

Historian David Wondrich's recent research led him to conclude that the Rob Roy cocktail was a creation borrowed from Duke's House in Hoboken, New Jersey. The story goes that a salesman for Usher's Scotch was invited to join a table of men drinking Manhattan's at Duke's and he said he would only join them if a round of drinks were made using his company's scotch. The bartender, Henry A. Orphal, created the Rob Roy using Usher's Scotch and it was a hit. Another historian claims that the birthplace of the Rob Roy was the swank Fifth Avenue Hotel, just up the street from the Waldorf.