Mad Men Inspired Chocolate Bourbon Cherry Cookies

Warning- This post may contain spoilers… but only if you never saw the very first episode of the very first season of Mad Men. If you’ve seen that you’re probably good.

In a way, I’ve always associated Mad Men with baking cookies.

When the first season started, in 2007, I was preparing for Ellie’s first birthday party. It was, more or less, the first time I had made decorated cookies. Then every year after, the first episode of the season fell around the time of her birthday (for the first three seasons, at least). So I spent many late nights watching Don pathologically cheat on Betty while decorating birthday cookies and packing up party favors.

To celebrate the premier of the sixth season on April 7th, naturally I wanted to make cookies. Just not the decorated kind. The cookies I wanted to make reflect Don’s recurring downward spirals  a drink that was popular during the era. An Old Fashioned. Only, instead of bitters, I used chocolate- for obvious reasons.

Chocolate Bourbon Cherry Cookies (Ellie's Bites)


  • 1/8 cup plus 2 TBSP bourbon
  • 1/8 cup maraschino cherry juice (or grenadine)
  • 1 stick of unsalted butter (room temp)
  • 1/3 cup brown sugar
  • 1/3 cup granulated sugar
  • 1 egg (room temp)
  • 1 tsp vanilla
  • 1/4 cup cocoa powder (I use Hershey’s Special Dark)
  • 1/4 tsp baking power
  • 1/8 tsp salt
  • 1 1/2 cups flour
  • 30 maraschino cherries (roughly one per cookie- I can usually get about 2 1/2 dozen out of a batch)
  1. In a small sauce pan, bring 1/4 cup of the bourbon and the grenadine to a boil. Reduce to about a Tablespoon. (About 5 minutes or so- keep an eye on it) Let cool.
  2. Preheat oven to 325F and line two- three baking sheets with parchment.
  3. In the bowl of an electric mixer with a paddle attachment, blend the butter and both sugars.
  4. Add the egg and mix well.
  5. Mix in the vanilla and the other 2 TBSP of the bourbon.
  6. Sift in the cocoa powder, baking powder, salt, and flour. Mix until combined.
  7. Mix in the cooled cherry/ bourbon mixture
  8. chocolatecherrybourbon cookies (Ellie's Bites)
  9. (Apparently the picture is the 8th step so don’t worry that there is something missing…..) Using a tablespoon sized cookie scoop, scoop the dough onto the prepared cookie sheets.
  10. Use the back of a spoon to make a little indentation in the ball of dough, place a cherry in the indentation.
  11. Bake for 10-12 minutes. Cool for five minutes or so then remove from pan to cooling rack. These are really good warm from the oven. There isn’t too strong of a bourbon taste. If you let them cool completely, you’ll taste the bourbon a bit more.

You can definitely soak cherries IN bourbon, but I have small children with sneaky cookie stealing hands so, for the time being, I tend to avoid recipes where the alcohol doesn’t bake out.

So, make these and pour yourself a Canadian Club and tune into AMC Sunday night to watch with me. (I’ll be putting my obsessive Netflix Dean Winchester Supernatural viewing on hold for the night.)

I’m linking these up to Simply Sweets Saturday at Simply Sweets by Honeybee.

 Simply Sweets by Honeybee 

Also, don’t forget to check in at The Cookie Puzzle for a month of posts in honor of Autism Awareness Month. Please take the time to tell Kim what an incredible thing she’s doing!


2 thoughts on “Mad Men Inspired Chocolate Bourbon Cherry Cookies

  1. wow! i really like your blog, and me and my husband we love mad men…this is a wonderful recipe, i can not wait to prepare, thank you….

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