There's something very grown up about a Whiskey Sour. It reminds me of that amusing moment in Whit Stillman's "The Last Days of Disco" when Chloë Sevigny, trying to be sophisticated and avoiding the "preppy girl's cliché of the Vodka Tonic" orders a "Whiskey Sour" at a thinly disguised Studio 54.
Incidentally, for all you Scots out there, it is a Whiskey Sour with the e. The drink's based on Bourbon, rather than Scotch Whisky, so I'm going to keep to the authentic American spelling for now. But according to wipkipedia, the Whiskey Sour was invented by an Englishman, one Eliot Stubb, who opened a bar in the port of Iquique, Peru. He added lime juice and sugar to a glass of whisky and was pleasantly surprised by its refreshing taste.
There's another theory that the earliest mention of the Whiskey Sour can be traced to a newspaper recipe in Wisconsin in 1870. I've got a sneaky feeling that the authentic recipe is more likely to be American; it might even have the whiff of Prohibition about it. The slightly sweet taste of Bourbon balances out well with the acidity of lemon.
Like all the great and classic cocktails, a genuine Whiskey Sour is simplicity itself. No chunks of pineapple, no silly umbrellas or fussy ingredients. You fill up your cocktail shaker with ice, pour in 2 oz of Bourbon Whiskey, the strained juice of half a lemon and two and a half teaspoons or so of powdered sugar. The cocktail is shaken and then strained into a cold glass, and garnished with a slice of orange peel and a cherry. If you follow these proportions you will make just enough to fill up a Martini glass- and I think that would work well.
You could also serve it on the rocks, and some people also add a splash of soda. Personally, I prefer it straight up, but as ever, it's a matter of personal choice, isn't it?