Lush Life

Frankie loves the clink of ice in well-filled glasses

Time magazine, August 1955.

There are more than several Classic Bourbon Cocktails, with sub-genres such as Highballs, Collins and Sours; the following drinks are undoubtedly amongst the aristocrats of good cheer. 

Manhattan

                                   2     measures of Rye/Bourbon or Tennessee Whiskey

                                 1/2   measure of Sweet (Red) Vermouth

                                 2-3   dashes of Angustura Bitters

                                   1     Maraschino cherry

Pour the liquid ingredients into a mixing glass filled with ice. Stir well, ensuring the drink is properly blended and chilled and then strain into a chilled cocktail glass. Garnish with the cherry before presenting. Several recipes suggest using orange bitters rather than Angustura and employing a strip of orange zest as an additional garnish. A 4-1 Manhattan (with double the whiskey) eschews orange or cherry in favour of a lemon peel twist, while a Dry Manhattan  and is simply chilled whiskey and  dry (white) vermouth sans any garnish.

At one time dubbed the King of Cocktails, this smart aperitif was at one point second only to the Martini as America's most widely sipped pre-dinner drink. One popular myth about this cocktail was that it was originated in New York's Manhattan Club sometime in the 1870's at a party hosted by Winston Churchill's mother Jenny, Lady Randolph Churchill. Combinations of bourbon and vermouth however were already popular in at least one Broadway bar a decade earlier.

Dry Manhattans were popular with all the members of The Rat Pack (excusing Joey of course) and Dean Martin in particular enjoyed them. There is also a story involving Sinatra that appears in several biographies that involves him arriving at a hotel in San Francisco and placing an order with room service for 88 Manhattans. Not that he was particularly thirsty, but he was annoyed that RKO had insisted he attend a premiere for a film of his that was not being particularly well received. He exacted revenge by abusing RKO's expense account - the trays full of cocktails stayed on trolleys in the hallway; he didn't even bother to drink one. Instead he took an entourage of 22 people to four different nightclubs; eventually returning to his room at 7am. Everything was charged to RKO. Sinatra never could stand being told what to do.