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."