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The Commodore is a Prohibition-era cocktail that shouldn't work as well as it does — and yet it's completely brilliant. Bourbon, crème de cacao, lemon juice, and grenadine shaken into a tart, chocolaty, fruity sour that keeps you guessing. The combination of chocolate and lemon sounds improbable until you taste it and realize they're doing exactly what salt and caramel do: each makes the other taste more like itself. The grenadine adds color and a berry sweetness that rounds the edges. It's a playful drink from an era when American bartenders were experimenting their way through Prohibition, and one of the better results of that experimentation.