At a very fancy dinner, everyone ordered cocktails. I enjoy simple drinks, like a Jameson, neat. I ordered a sidecar, because it sounded like something Frank Sinatra or James Bond would order. I received a tall sugar-rimmed cocktail glass with a bright orange drink and a pear slice balance delicately on the rim. I began a deep and contentious internal crisis for the rest of the evening, as to how I felt about this dainty pear drink, why I felt how I did, and how I could be fooled by such a sly waiter and so treacherous a cocktail menu. This crucible left me angry, confused, and buzzed. I look back on this experience with reverence towards the Pear Sidecar, and wisdom for similar adversaries which are sure to present themselves in my future.
Word to the wise: any cocktail that is popular is going to be bastardized by "mixologists" who somehow think they're entitled to a career for sloshing two or three fluids together. I was on a show once where the "secret" to their new cocktail was three drops of saline. See, it releases the flavor compounds... Thus we end up with this mess: Martini - used to be gin, vermouth and bitters. Is now "vodka and whatever the fuck we feel like adding." Cosmopolitan - used to be vodka and cranberry juice. Post sex-and-the-city is now whatever the fuck juice mixed with whatever the fuck white liquor they feel like. Margarita - used to be tequila, triple sec and lime. Is now a tequila slushy made with whatever the fuck they feel like. Daquiri - used to be rum, lime juice and maraschino. Is now a tequila slushy made with rum. Dollars to donuts you will never even meet a bartender that knows what maraschino is. There are cocktails you can order that are going to be exactly what you expect because they have never been inside a tedious HBO dramedy and because they're made with strong flavors that are hard to mask, which makes them more difficult to market to drunk sorority girls. They also likely will baffle the fuck out of your average "mixologist". Start with a Manhattan. This is bourbon and sweet vermouth. They will have bourbon, they will have sweet vermouth, so while they might ask you what goes into one (I have been asked "what's in a Manhattan?" by servers at Michelin Star restaurants) they will be able to make it. If they know what a Manhattan is, they probably know what an Old Fashioned is (bourbon, bitters and a sugar cube). they probably don't have sugar cubes. Because the only thing they're good for is Manhattans. This is why Mojitos ceased to be mojitos. It's a bitch keeping the mint leaves around. If they have a whiskey list they will probably be able to make you a Rusty Nail. This is scotch and Drambuie. Drambuie is another single-purpose ingredient; it's useful pretty much for Rusty Nails and nothing else. If you really want to shoot the moon, you can go for a Sazerac. This is rye, a sugar cube and absinthe. It will probably cost you a lot because only hipsters drink absinthe. For future reference, you likely won't go wrong with a scotch and soda. Specify a blend. Johnny Walker, for example. Also, if you want to annoy people drink Bushmill's instead of Jamison because it's "protestant whiskey."
I feel like Old Fashioneds have been a more and more common occurrence on drink menus lately. In the hipster universe I live in, "classic" cocktails are really making a comeback. But most often you're either at a cocktail bar where you're better off trying one of their house mixes (that's gonna set you back 18$ if your friends drag you to a trendy speakeasy) , or you're at a non cocktail place where you gotta play it safe with a gin tonic or a tom collins if feeling adventurous...
Every other time I order a Rusty Nail, the bartender either has to ask me what it is or wonders if they even have Drambuie. I've already spotted it, because goddamn what's more annoying than people ordering a drink that the bartender can't make? They then reach way back behind some goddamn nut liquor to pull it out. You can see the dust trailing off the bottle as it crosses to the pour station to fill me up. I don't love it as a drink but I like one once in a while. I always put the bitters on the sugar cube for an old fashioned. drop a quarter of an orange wheel and cherry in with half the ice you'd put in a regular bucket and muddle the shit out of it. Shake and pour the whole thing in the bucket. Rinse the shaker with a sprits of soda and dump it into the bucket. It's my favorite old fashioned, no garnish.
We have reached an era where you're better off knocking the "mixologist" off his equilibrium than you are trusting him. Case in point - you're no longer tending bar, I'm no longer working in bars, and nobody aspires to be a "bartender" anymore. It's "mixology" now.