Rye is that quintessentially American whiskey. It's Rye that Humphrey Bogart drinks in The Big Sleep in part because it's so very American. Here, watch it yourself:

In the roaring twenties, before Prohibition, and in the speakeasys during Prohibition, American Rye flowed freely. OK, patrons paid for it, but Rye was abundant, widely available and a uniquely American spirit. As cocktails became popular, the distinctively savory flavor of Rye whiskey became a base ingredient for a wide range of cocktails in part because it is individual enough that contribute to the overall flavor, without being drowned by too much sweet. Rye is also especially lovely with citrus; the two flavors enhance each other and something marvelous emerges. There are three cocktails in particular that are intimately associated with Rye; the Manhattan, the Old Fashioned, and the Sazerac.

The Manhattan, while currently most likely to be made with Bourbon, was traditionally, and initially, a Rye cocktail. As Rye returns to popularity, the Manhattan is doing much the same. There are a variety of creation myths around the birth of the Manhattan; the truth is most likely something that lies between them. I'm quite willing to believe that the particular recipe that lies at the core of all Manhattans was established long before the name Manhattan was given to the drink. But, so legend has it, a famous American socialite and hostess named Jenny Jerome, later better known as Lady Churchill, the mother of Sir Winston Churchill, threw "the" party in 1870 at The Manhattan Club in New York City, in order to celebrate the victory of Samuel J. Tilden, then the Governor Elect of New York. She wanted something special to drink in honor of the occasion, and the bartender offered up a concoction of Rye, Sweet Vermouth, and a dash of Bitters. The cocktail was dubbed "The Manhattan" in honor of the club. Back then, the Manhattan called for two parts Vermouth to one of Rye, and two or three dashes of Orange Bitters. Today, most Manhattans are made with two or three dashes of Angostura Bitters.

There are now a number of Manhattan variations; the most common version uses far less vermouth (as in sometimes a capful or less) and an ounce and a half to two ounces Rye. There's a version called the "Perfect Manhattan" which calls for equal parts Sweet and Dry Vermouth, over ice, stirred gently, and then served in a chilled Martini glass. The Perfect Manhattan is typically garnished with a lemon twist, rather than the customary Maraschino cherry. For my part, fond as I am of a Rye Manhattan, keep the Maraschino far far away; an orange slice will do very nicely, thanks. For those who want the specifics of Manhattan creation, look here.

If the Old Fashioned was not the first cocktail, it was one of them (some point to the Sazerac as the very first) there are recipes for this drink (whiskey, sugar, a splash of water to dissolve a teaspoon of sugar, a dash or so of Angostura Bitters, muddled together with an orange slice or cherry if you wish) under the name "Whiskey Cocktail" in the late 1800s. Recipes call for the drink to be made with either Rye or Bourbon. The water is sometimes soda water; sometimes a bar will use simple syrup instead, to save time, and, perhaps, to avoid a tiny mound of undissolved sugar at the bottom of the glass. The more modern trend of using more than a teaspoon or so of water to dissolve the sugar is a bit of a religious issue for some; if you like to top the glass off with soda water, then by all means, you should. If you don't, then don't. I note that that "Drink Boy" has a fabulous article, with fifteen or so recipes for Old Fahioneds, going back to the late 1800s. That said, I like an Old Fashioned made with Bourbon, but there's something very nice about Rye's ability to stand up to the sugar and citrus and contribute a complex element of its own flavor that makes a very special Old Fashioned. I also note that it's fun to try a lemon twist, instead of orange, but that best of all for my mind is a splash of orange-essence flavored soda water, and kumquats. Kumquats are cute, small, round, taste good, and you can skewer them on a toothpick, without the nasty, syrupy cherry taste.

The Sazerac is as closely tied to New Orleans as chicory coffee and beignets. The Sazerac was the creation of one Antonine Amadie Peychaud, an apothecary from the West Indies who moved to New Orleans and set up his shop in the early 1800s, in the French Quarter (the site is still marked today). Among other sorts of medicines, Peychaud created and sold aromatic bitters from a family recipe. Sometime during the 1830s he began making a toddy for friends based on brandy, sugar and his family's bitters, with a bit of water to dissolve the sugar. The fame of the toddy spread, and, in 1853, one Sewell Taylor, owner and operator of the Sazerac Coffeehouse ("coffeehouse" back then meant "bar"), began to serve the Peychaud's toddy, with a few differences. First, he made it with Sazeral-du-Forge et fils cognac, a cognac which he imported. In fact, Taylor was the only importer, and, in short order, the toddy was renamed the Sazerac. One or more of the bartenders began to coat the serving glass with a few drops of absinthe before adding the cocktail. In 1870, a new owner took possession of Sazerac Coffeehouse. The new owner, Thomas Handy substituted Rye for the Cognac, and, from that point on, the Sazerac was firmly tied to Rye. Over time, the Sazerac House bartenders also began to add a dash of Agnostura Bitters in addition to Peychaud's, and, when Absinthe was no longer safe or readily available in the U.S., New Orlean's Herb Saint, an anise flavored liquor was substituted. Absinthe is now legal, or at least some of it is, in the U.S. but Herb Saint is more readily available, still. I urge you to read this page for all a more complete discussion regarding the ultimate Sazerac.