Frank Sinatra drank expensive red wines, and mixed martinis for his friends on the set of "Ocean's Eleven." And, he never forgot a pal's favorite drink (according to Sinatra's old friend Ed McMahon). But his own drink was a simple, but exacting mix of ice, Jack Daniels Tennessee whiskey and water. "This is a gentleman's drink," is how he described it. "This is nice." He called it "The Black Ass of Jack Daniel," on occasion.
Use a leaded crystal glass, if possible. Sinatra was a fan of elegant glassware, and built a voluminous collection. He believed that good glassware brought out the best in any booze.
Drop four cubes—no more—into the glass. Sinatra would pick out any more cubes than four with a spoon, and admonish the bartender that he wanted to drink, not skate.
Pour two fingers of Jack Daniels over the ice—no more. His bodyguards would tell bartenders "Don't try to be his friend by mixing it heavy. He don't like it like that." Sinatra once described a drink too heavy in whiskey as "Sammy Davis in a glass."
Fill the remainder of the glass with a quality still water, like Poland Springs. Sinatra drank water only as a cocktail mixer, never for refreshment, or even as a back to a cocktail. "I'm thirsty, I'm not dirty," he would scowl.
Allow the drink to settle for two minutes. Sinatra would drink martinis right on pouring, but believed that allowing a mixed drink on the rocks allowed it to settle, and brought out its subtleties.
Drink your Black Ass of Jack Daniel Sinatra's way. He did not hold cocktails by the rim, and infrequently set them down. He would cup them in his hand, insulated by a cocktail napkin.