This cocktail is unusual in that both the drink and the word originated during Prohibition. The drink came from Paris (birthplace of the Boulevardier) and the word came from Boston (birthplace of the Ward 8). 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.
2 ounces rye (Rittenhouse or Bulleit work nicely)
1 ounce dry vermouth (Noilly Prat is top notch)
Juice from 1/8 a lemon
.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.
Thanks to Herbs & Rye, a great off Strip bar and restaurant in Las Vegas, for introducing me to this cocktail. I knew I would like the place as soon as I saw that it listed its cocktails by era.
Just remember -- cocktail history is part of American history. So appreciate history and have a Scofflaw!