The Painkiller was created in the 1970s at the Soggy Dollar Bar on Jost Van Dyke in the British Virgin Islands. The inventor was Daphne Henderson, and the drink originally used Cruzan Rum before Pusser's Rum trademarked the name in 1989.

Hot Buttered Rum dates to colonial America in the 1650s when New England distilleries began producing rum from Caribbean molasses. Colonists added rum to hot drinks like toddies, incorporating butter and spices to create this warming winter beverage.

The Rum Old Fashioned is a variation on the classic Old Fashioned cocktail, substituting aged rum for whiskey. The Old Fashioned formula dates back to the early 1800s, and rum versions appeared in cocktail guides including Trader Vic's 1947 Bartender Guide.

The Mary Pickford cocktail was created in 1920s Havana, Cuba during Prohibition. Named after silent film actress Mary Pickford, it was credited to either bartender Fred Kaufman or Eddie Woelke and first appeared in print in Basil Woon's 1928 book.

El Presidente originated in Cuba during the 1910s and appeared in the 1915 Manual del Cantinero. Named after a Cuban president—either Mario García Menocal or Gerardo Machado—this elegant cocktail became popular during Prohibition when Americans traveled to Havana.

The Hemingway Daiquiri was created at El Floridita in Havana by bartender Constantino Ribalaigua Vert for Ernest Hemingway. Originally called the "Papa Doble," the drink featured double rum and no sugar to accommodate Hemingway's diabetes.

The Cuba Libre originated in early 1900s Cuba following the Spanish-American War. The name means "Free Cuba," the battle cry of Cuban independence fighters. Distinguished from a simple Rum and Coke by the essential addition of fresh lime juice.

Planter's Punch originated in Jamaica and first appeared in print in September 1878 in London's Fun magazine. This classic rum cocktail follows the famous rhyme "one of sour, two of sweet, three of strong, four of weak," referring to lime juice, sugar, rum, and water.

The Hurricane was created in the 1940s at Pat O'Brien's bar in New Orleans' French Quarter. Born from necessity when bar owners were required to purchase large quantities of rum to obtain whiskey, this sweet, potent cocktail became an iconic symbol of New Orleans.

The Zombie was invented in 1934 by Donn Beach at his Hollywood restaurant Don the Beachcomber. This legendary tiki cocktail combines three types of rum with fruit juices and secret ingredients, becoming so potent that Beach limited customers to two per visit.

The Dark 'n' Stormy was created in Bermuda shortly after World War I when British sailors combined Gosling's Black Seal rum with ginger beer. This trademarked cocktail is one of only a handful of legally protected drink recipes worldwide.

The Mai Tai was created in 1944 by Victor "Trader Vic" Bergeron at his Oakland, California restaurant. This tiki cocktail features aged rum, fresh lime juice, orange curaçao, and orgeat syrup, named after a Tahitian phrase meaning "out of this world."

The Piña Colada was created in 1954 by bartender Ramón "Monchito" Marrero at the Caribe Hilton in San Juan, Puerto Rico. This tropical cocktail combines rum, coconut cream, and pineapple juice, becoming Puerto Rico's official drink in 1978.

The Daiquiri was invented in 1898 by American mining engineer Jennings Cox near the Cuban village of Daiquirí. This classic cocktail features just three ingredients—white rum, fresh lime juice, and sugar—creating a perfectly balanced sour.

The Mojito is Cuba's most famous cocktail, with origins tracing to the 16th century drink "El Draque." This refreshing highball combines white rum, fresh mint, lime juice, sugar, and soda water, gaining worldwide fame through Havana's bar culture.

The Brandy Sangaree is a historic drink dating to at least 1774. Named from the Spanish word "sangre" (blood), this colonial-era cocktail features brandy, sugar, and nutmeg, and was included in Jerry Thomas's influential 1862 bartending guide.

The East India Cocktail first appeared in Harry Johnson's 1882 Bartender's Manual. Named after the British East India Company, this elegant brandy cocktail originally featured raspberry syrup before evolving to include pineapple syrup by 1888.

The Baltimore Bracer is a classic cocktail first appearing in Jacques Straub's 1913 manual. Named after Baltimore, Maryland, this bold drink combines brandy with anisette liqueur and egg white for a distinctive licorice flavor and frothy texture.

The Japanese Cocktail is a classic brandy drink first published in Jerry Thomas's 1862 How to Mix Drinks. Created to honor Japan's first diplomatic mission to the United States in 1860, this cocktail combines brandy, orgeat syrup, and bitters.

The Coffee Cocktail is a classic drink from Jerry Thomas's 1887 Bar-Tender's Guide that contains no coffee despite its name. This rich, creamy cocktail combines brandy, port wine, egg, and sugar for a coffee-colored flip.