As long time readers should know, though I enjoy inventing new cocktails and having fun with mixology, at heart I adore the classics. My two favorites are the Martini and Manhattan, and which one I prefer at any given moment depends a lot on mood and atmosphere and the ingredients at hand.
A bad but serviceable Martini can be made in pretty dire circumstances: a clear liquor, a shaker of ice, and a brined vegetable or strip of citrus peel, and you can achieve something bracing but able to perform the work at hand. I prefer a Martini as an aperitif, something strong but bracing and crisp that gets you ready for four courses and half a dozen different wines.
The Manhattan is different. It requires a higher degree of civilization. Whiskey/Whisky can be found everywhere, but bitters and Sweet Red Vermouth are a must, and so many bad variations are made in bars that it's often a losing proposition to order one in the first place. I once ordered said cocktail in a bar that shall not be named, and the bartender said, "Manhattan. Got it. Crown Royal and Dr. Pepper. Give me one second." And I said, "Do you kiss your mother with that mouth? Good day, sir!" I swear that the silk ribbon on my top hat positively wilted at that egregious faux pas.
Your worst Martini might have ruined rotgut vodka that spent a few hours in steel tubing, but a bad Manhattan ruins years of barrel aging in oak. Keep these things in mind when you're mixing drinks.
When I'm in the mood for a Manhattan, it's normally with the company of other guys and as a prelude to a dinner of hearty red wines and lots of rare red meat. To do it properly, you need control over your own ingredients. Better, older whiskey will make for a better Manhattan, and quality bitters are essential.
Here I lined up the various components I assembled after a long, hard day at work, and a desire for something relaxing but dignified: