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Whiskey Cobbler

The cobbler is one of the oldest drinks in a bartender’s arsenal, and once upon a time, it was the most popular drink in the United States. It’s fallen from popularity somehow, and other writers (David Wondrich, in his Imbibe!, for example) have tried to resurrect it. I wish more people would try the cobbler. I had a sherry cobbler in Boston while promoting my first book, and I fell in love. The sherry cobbler, in fact, is the oldest version of the drink, arising in the 1830s. It’s a refreshing tipple—low in alcohol, icier than a julep, and very mildly fruity. The whiskey variation is, of course, a stronger, more bracing drink. But sometimes that’s what you want.


  • 4 ounces rye whiskey high-proof, like Rittenhouse
  • 1 tablespoon simple syrup
  • 3 orange slices
  • Berries (optional; ideally fresh, local, and seasonal—so if you’re making this in winter,
  • I wouldn’t bother)


  • Crack a whole lot of ice. You want something like little pebbles. Best bet: Fill a gallon-sized zipper bag with ice, place a towel over it, and wallop it with a rolling pin, meat mallet, or saucepan.
  • Fill a shaker with the cracked ice, as much as you can fit. Add the whiskey, simple syrup, and orange slices.
  • Shake vigorously to combine.
  • Pour unstrained into a collins glass. Add more ice if you want and stir.
  • Garnish with berries, if using.


Recipe reprinted with permission from Whiskey © 2016 by Michael Dietsch, The Countryman Press.