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Chill a cocktail coupe by filling it with ice water or placing it in the freezer.

Combine bourbon, Cynar, simple syrup, chocolate bitters, and bitters in a mixing glass.

Add ice to the mixing glass and stir until well-chilled.

Strain the mixture into the chilled cocktail coupe.

Express the oils from a lemon peel over the drink, rub the peel around the rim, and drop it into the cocktail.

For an alternative presentation, serve the cocktail over one large ice cube in an Old Fashioned glass if preferred.