The Brandy Alexander is a well known retro cocktail, but…
Cynar is a bitter amaro that tends to be pretty polarizing at the bar. People either love it or hate it (and if they haven’t heard of it, they tend to have a strong reaction one way or the other after they do). It’s bittersweet, herbacious and strongly flavored enough that it can be difficult to work into a cocktail. This drink solves that problem by pairing Cynar with a couple of other very potent liqueurs: Campari and Luxardo Maraschino.
The base of the cocktail, The Italian Job, is actually bourbon and the three other ingredients are added in equal measure. When combined. you end up with a cocktail that has the vanilla smoothness of bourbon, the orange of campari and an interesting hint of cherry. While the herbacious Cynar is still present, it actually serves to temper the maraschino more than dominate, yielding a nicely balanced drink. If you’re a Manhattan fan or if you simply enjoy amaros, this should make a nice change of pace.
For me, the orange twist is what really makes this cocktail. The aroma of the fresh orange brings out the sweetness of the Campari and rounds out the drink. If you don’t have a fresh orange, consider going to pick one up before making this. Fresh grapefruit juice also brings in a nice note, if you happen to have that on hand, but it gives the drink an entirely different (though also very pleasant) finish.
1 1/2-oz. Bourboun
Pour all of the ingredients into a mixing glass and fill with ice. Shake and strain into a chilled martini glass. Squeeze an orange twist over the drink, then rub the peel around the rim of the glass. Drop the twist into the drink before serving.