The Scofflaw is unusual in that both the word and the cocktail originated during Prohibition. In 1923 a Boston newspaper sponsored a national competition to create a term defining a lawless drinker, and the word "scofflaw" was the winning entry. It immediately entered the popular vernacular and has been with us ever since. One year later Harry's Bar in Paris created the Scofflaw.
2 ounces rye
1 ounce dry vermouth
.25 ounces lemon juice
.75 ounces glorious grenadine syrup
2 dashes orange bitters
Combine in a shaker with ice, shake like you're running from The Untouchables (your choice about whether Robert Stack or Kevin Costner is Eliot Ness), and strain into a chilled glass.
Combining rye and vermouth in the Scofflaw works well because the vermouth tempers (historical pun intended; the temperance movement was a driving force behind Prohibition) the strong, spicy flavors of the rye. The lemon juice and orange bitters give the Scofflaw a little acidity. The grenadine brings some sweetness to the equation, and in turn keeps the Scofflaw from burning your insides like a gangster would burn their rival’s stash.
Just remember: cocktail history is part of American history. So appreciate history and have a Scofflaw!