I wasn’t much of a whiskey drinker until I moved to Chicago, where a regular administration of brown liquor is pretty much a necessity to make it through the winter. At first, my whiskey drinking was strictly utilitarian; one of the bus stops where I’d regularly switch to a different line was also right in front of a bar, so on particularly cold nights I would get off one bus, run inside, shoot some cheap bourbon, and run back across the street before the next bus came, feeling slightly more fortified against the single-digit weather.
It wasn’t long, though, before I truly fell in love with the stuff—particularly the peppery bite of rye—and ever since my first Chicago winter I’m automatically drawn to any cocktail that includes it. So when I was flipping through a copy of the 1956 edition of the Esquire Drink Book, the first page I bookmarked was the opener to the “rye and bourbon” section, full of variations on the Manhattan. My favorite was a vermouth-heavy twist called a Horsecar: Instead of the Manhattan’s 2:1 ratio of rye to vermouth (in a “Perfect Manhattan”, half the vermouth is dry and half is sweet), the Horsecar is equal parts rye, dry vermouth, and sweet vermouth. The result is a sweet-but-not-syrupy cocktail that goes down nicely on a chilly day. Even if you’re not trying to make it through a Chicago winter (and if you are, I feel for you), it’s the perfect drink to keep you company while you wait patiently for spring’s return.