The oldest bourbon cocktail is the Old Fashioned. Originally called a “cocktail,” as it was about the only one you’d get, so further clarification wasn’t needed. It's my go-to drink.
From here we develop the old fashioned’s slightly more posh descendant: the Manhattan. The Manhattan is more or less the same except turned into a form resembling a martini.
Jumping sideways a bit, we come to another classic simple bourbon cocktail: the Boulevardier. A much less common, but no less delicious, variation of the Manhattan, this drink is something like a Manhattan.
Finishing with the heavier, more cherry-like cocktails and moving into the zesty and lighter options, our first stop should be a Whisky Sour.
Moving on to other frothy, icy things, we have what comes in as an absolute classic and arguably DC native: the Mint Julep. Definitely a favorite of the Kentucky Derby.
The mint julep’s cousin has to be the Bourbon Smash, and a particular favorite of mine, often after I’ve already had one or five.
And finally, one of my absolute favorites that I almost never drink: the sazerac. This historic drink comes from New Orleans.