Rye, Cognac, sweet vermouth, Bénédictine, and dual bitters — New Orleans 1938. Possibly the most complex stirred cocktail.
The Vieux Carré was created by Walter Bergeron, head bartender at the Hotel Monteleone in New Orleans in 1938. The Hotel Monteleone had opened in 1886 and its bar — the Carousel Bar, which literally rotates — is one of the great cocktail institutions in America. The name means 'Old Square' in French, referring to the French Quarter.
The Vieux Carré is the most complex of the great stirred cocktails — more so than a Manhattan, more than a Negroni. It combines two spirits (rye and Cognac), a fortified wine (sweet vermouth), a herbal liqueur (Bénédictine), and two bitters (Peychaud's and Angostura). Each ingredient represents a different tradition: American whiskey, French Cognac, Italian vermouth, French Bénédictine, and New Orleans bitters. The drink is the entire cocktail history of New Orleans in a glass.
Replace one of the bitters with orange bitters. The citrus note lifts the heavier base.
Replace Cognac with bourbon. A more accessible version that loses the French-American duality but gains a richer caramel note.
Replace the rye whiskey with mezcal. The smoke plays beautifully against the Cognac and Bénédictine's herbal complexity.