Every banana bread old fashioned I found does it the same way. Bourbon, a pour of banana liqueur, brown sugar syrup, walnut bitters. Nothing wrong with that. It just tastes like banana candy sitting next to a whiskey.
Banana bread doesn't taste like that. The banana goes dark and sticky in the oven, the sugar gets deep, and there's usually a little salt in there keeping it from tasting like dessert syrup.
So this one skips the liqueur. The bananas get roasted in their peels until they go black, then simmered with dark brown sugar, a cinnamon stick, and a pinch of salt, and the syrup carries the banana bread part while the bourbon stays in charge.
Use the ugliest bananas on your counter, the ones nobody in the house will eat anymore.
What you need
For the roasted banana syrup
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2 very ripe bananas, peels heavily speckled or mostly brown
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1/2 cup packed dark brown sugar
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1/2 cup water
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1 cinnamon stick
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1/4 teaspoon vanilla extract
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Small pinch of salt
For one cocktail
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2 ounces bourbon
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1/4 ounce roasted banana syrup
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2 dashes Angostura bitters
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1 dash orange bitters
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1 large ice cube
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Orange peel, for garnish
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Freshly grated nutmeg, for finishing
Directions
Make the syrup
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Heat the oven to 400°F. Put the unpeeled bananas on a lined sheet pan.
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Roast for 15 to 20 minutes, until the peels are black and the bananas feel soft all the way through.
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Let them cool enough to handle. Scoop the flesh into a small saucepan and throw out the peels.
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Add the brown sugar, water, cinnamon stick, and salt.
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Bring it to a gentle simmer and cook for 5 minutes, mashing the banana as you stir.
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Take it off the heat, stir in the vanilla, and let it sit for 15 minutes.
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Strain through a fine mesh sieve. Let it drip. Don't press on it, or the syrup goes cloudy and thick.
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Cool completely, then keep it in a covered jar in the refrigerator.
Make the drink
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Add the bourbon, syrup, and both bitters to a mixing glass.
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Fill with ice and stir for about 30 seconds, until it's very cold and a little diluted.
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Strain into a rocks glass over one large ice cube.
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Twist the orange peel over the glass so the oil hits the drink, then drop it in.
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Grate a little nutmeg over the top. Barely any. Nutmeg takes over fast.
A few things worth knowing
Bourbon. Look for one that already leans vanilla and caramel, since it meets the banana halfway. A very spicy, high rye bourbon will fight it.
Sweetness. Start with 1/4 ounce of syrup. It should still taste like whiskey first. If the banana disappears, go up to a scant 1/2 ounce, because bananas vary and so does everyone's sweet tooth.
Orange, not walnut. Most versions use walnut bitters. Orange keeps it brighter and leaves the banana bread idea to the roasted banana. For the nutty version, swap the orange bitters for a dash of black walnut. My take: try it with orange first.
No brown butter, for now. Brown butter washed bourbon would push this even closer to banana bread. The sources I read don't agree on how to store it or how long it keeps, so it's not in this recipe.
Make it for a crowd
For eight drinks, stir 16 ounces bourbon, 2 ounces syrup, 16 dashes Angostura, and 8 dashes orange bitters in a pitcher with plenty of ice. Stir for about a minute, strain into a bottle, and keep it cold. Pour over big cubes and garnish each glass.
Good with
Anything salty and a little rich. Aged cheddar, spiced pecans, or a slice of actual banana bread.