There comes a time in every man’s life when he decides he needs to branch out, booze-wise. So it was with me. I wear sophisticated suits. I attend business meetings. I work with large corporations. I have secretaries and assistants. I am Don Draper. I want to drink like Don Draper.

Drinking liquor “neat” is a classic move but boring. So I decided to focus on classic cocktails made with whiskey. I put in my time at Oldfield’s Liquor Room and Seven Grand in Los Angeles to test a series of vintage drinks. Over a few weeks I came up with the five best cocktails that any man can order with confidence.

Order these with my suggested whiskey, and you’ll get the respect you deserve. Want to go the extra mile? Use our cocktail-party facts to strike up a conversation.

 

Sazerac

Sazerac
As America’s oldest cocktail, this is as classic as you can get. The Sazerac was named after Sazerac de Forge et Fils brandy, its original prime ingredient, and is now served with rye whiskey along with sugar, absinthe and Peychaud’s bitters. If you like a combination of sweet and bitter, this is the drink for you.
Order it with: Sazerac brand Rye Whiskey
Cocktail party fact: The Sazerac is New Orleans’ official cocktail but efforts to make it Louisiana’s official state cocktail failed.

 

Manhattan

Manhattan
Some historians say this classic was created at the Manhattan Club in New York City in the 1870s. Traditionally it’s made with rye whiskey, sweet vermouth, and bitters and is garnished with a cherry. I prefer drinking it with bourbon, which gives it a sweeter flavor.
Order it with: Elijah Craig 12-Year-Old Bourbon
Cocktail party fact: The Manhattan is not the only cocktail to be named after a New York City borough. The Brooklyn is a sweeter version of the Manhattan and is made with rye whiskey, dry vermouth, maraschino liqueur, and orange bitters. There are cocktails named for the other New York boroughs, but ordering a Queens or a Bronx won’t get you any respect.

 

Rusty Nail

Rusty Nail
The Rusty Nail is one of my favorite sipping cocktails. You can thank Club 21 in New York City for giving this classic drink its extra-manly name. (It was previously known by more unfortunate names including the Knucklehead.) The Rusty Nail made with just two ingredients: a blended scotch whiskey and Drambuie and is perfect if you like a strong drink with a little sweetness. It is traditionally made with 2-to-1 scotch-to-Drambuie mix, but some like it dryer, using a 3-to-1 or 4-to-1 ratio.
Order it with: Dewar’s 12 -ear Scotch
Cocktail party fact: The Rusty Nail was one of the favorite cocktails of the Rat Pack.

 

Whiskey Sour

Whiskey Sour
The Whiskey Sour is a great option if you’re looking for a vintage cocktail that’s sweeter than a Sazerac. A traditional Whiskey Sour is made with bourbon or rye whiskey, fresh lemon juice, and sugar. Make it more interesting by ordering it with egg white and honey instead of sugar.
Order it with: Jack Daniel’s
Cocktail party fact: The Whiskey Sour is the official drink of University of Virginia’s 189-year-old Jefferson Literary and Debating Society. The society’s members have included poet Edgar Allan Poe and President Woodrow Wilson. Only the best debating societies have official drinks.

 

hemingway-daiquiri

Hemingway Daiquiri With Rye
There may be no manlier drink than one created by literary god Ernest Hemingway. The Hemingway Daiquiri is said to have been born in Havana when Hemingway asked for a daiquiri without sugar but with double the rum. Today the Hemingway Daiquiri is served with sugar to add some sweetness to an otherwise strong drink. It’s usually made with light rum, lime juice, grapefruit juice, sugar and maraschino liqueur. Order it with rye whiskey instead for a drink that is truly mind-blowing.
Order it with: Old Overholt Rye
Cocktail party fact: A drink named after Hemingway begs to be sipped while quoting Hemingway. My favorite Hemingway quote: “I drink to make people more interesting.”