This Secret Tiki Cocktail Tastes Like a Tropical Vacation in a Cup

As a full-blown tiki fanatic, the Painkiller was my favorite cocktail for a long time. It’s a delicious combination of dark rum, pineapple juice, orange juice, and cream of coconut. 

Then I tried my first Soggy Dollar. 

I was at New York’s Lullaby Bar one night when former general manager Daniel O’Grady, who shares my fondness for the Painkiller, surprised me with this latte-colored concoction topped with grated nutmeg. 

It was love at first sip. It tasted like coffee, coconut, pineapple, baking spices, and like any good tiki drink, a tropical vacation in a cup. It wasn’t on the menu, but O’Grady told me that the Soggy Dollar was created by Brother Cleve, the Boston bartending icon who had helped open Lullaby before he passed away in 2022.

Brother Cleve, who started out life as Robert Toomey, was a musician, DJ, record producer, and bartender widely regarded as the godfather of the Boston craft cocktail scene.

“Back in the ‘90s, there were all these different branches of loungecore,” says Jeff “Beachbum” Berry, tiki historian and co-owner of New Orleans’ acclaimed bar Latitude 29. “There was tiki, rockabilly, lounge, Vegas Rat Pack, swing, hot rod culture — all these things were part of the whole retro alternative music scene, and the king of all that was Combustible Edison.”

Cleve was on keyboard for the brand, and part of its act was making classic cocktails on stage. 

Brother Cleve’s Soggy Dollar is a riff on the Painkiller. Even its name is an ode to the place where the Painkiller was invented: The Soggy Dollar Bar, located on Jost Van Dyke in the British Virgin Islands. Due to the beachfront bar’s specific location, most customers access it by boat. And since there is no dock, beachgoers either get to shore by dinghy or by simply swimming ashore — hence the bar’s cheeky name. 

An Improved Painkiller

Looking at Cleve’s recipe, the drink shouldn’t work, since it's anchored by two-and-a-half ounces of Cruzan Black Strap Rum. “Cruzan Black Strap is a very unique rum,” says Brian Miller, head bartender at New Jersey’s Stockton Inn. “There’s kind of a maple syrup flavor going on and a little bit of coffee.” 

The remainder of the drink’s recipe calls for ingredients that appear in a classic Painkiller, including pineapple juice, orange juice, coconut cream, and a grated nutmeg garnish. As well as some falernum (a rum-based liqueur with lime, ginger, almonds, and baking spices) and Fee Brothers’ Whiskey Barrel-Aged Bitters.

But the Soggy Dollar ingeniously doesn’t balance sweet and sour, but, thanks to the black strap rum, balances sweet and bitter. 

“The cocktail has this iced coffee vibe, and the rich, earthy notes of the black strap help balance the drink’s sweetness, which I think is why it works so well,” says Harrison Snow, co-owner and beverage director of Lullaby. “Black strap is also a really bold ingredient that can hold up to a lot of dilution.” 

As for the additions of falernum and bitters, Snow claims that they both bridge the gap between the base spirit and fruit components. Falernum brings a bright nuttiness and floral notes into the equation, and lifts the black strap’s profile to better complement the coconut cream, orange, and pineapple. Meanwhile, the barrel-aged bitters add another bump of spice and a bit of dryness from the tannins in the whiskey barrels. 

“It’s really a microcosm of Cleve’s legacy,” he says. “It's such an incredible, mind-boggling experience of a cocktail. Every time I put this drink in front of anybody, they've just been blown away by it.”

Brother Cleve’s Soggy Dollar

Ingredients

• 2 ½ oz Cruzan Blackstrap Rum
• 2 oz Pineapple juice 
• 1 oz Orange juice
• 1 oz Coco Reàl (or Coco López)
• ½ tsp Velvet Falernum
• ½ dash Fee's Whiskey Barrel Aged Bitters
• Garnish: grated nutmeg

Directions

1. Add all ingredients to a cocktail shaker with three large ice cubes.
2. Shake until chilled
3. Double strain into either a double rocks glass or tiki mug over crushed ice.
4. Garnish with grated nutmeg.