The head of the Negroni family isn’t, it might surprise you, the Negroni. The now-iconic drink is actually more like the third generation of the Campari-laced clan. The Milano-Torino was the first to mix Campari and sweet vermouth (a nod to these products’ respective origins), way back in the 1860s.

The Negroni emerged circa 1920, but doesn’t show up in bar manuals under that name until the ‘40s, when its equal parts mixture of London dry gin, sweet vermouth, and Campari. It was adopted as a favorite of cocktail revivalists in the aughts and 2010s, which has spawned countless variations.

The Americano mightn’t be just a lengthened Mi-To as previously assumed, but rather a genre of drink that combined vermouth with various liqueurs, especially aperitivo and amaro. Fernet-Branca was a popular option, but Campari won out by the ‘30s.

Sbagliato means “mistaken” or “bungled” in Italian. That’s a reference to the apocryphal tale told about why the Negroni Sbagliato features prosecco—and no gin. The resulting beverage is a delightful cross between the Americano and the Spritz.

Rabarbaro is a subcategory of amaro wherein Chinese rhubarb root is a main botanical. This ingredient is naturally smoky, which is a throughline flavor in the category, as is earthiness (roots will do that!). Producers can distinguish themselves through their choices of other botanicals.

A stirred drink from The Hoffman House Bartender’s Guide (1905), the Automobile Cocktail consists of equal parts Scotch, Old Tom gin, and Italian vermouth, plus a little gum syrup and orange bitters. I took this template and subbed in apple brandy for the Scotch, using alpine amaro in place of bitters, and sweetening with fig syrup. It’s Martinez-esque, but feels perfect for November with apple and pronounced piney notes. “Motor wagon” was a term used by some early car makers.

This drink is essentially a Vieux Carré with coffee liqueur subbed in for the Bénédictine, but with a touch of absinthe–influenced by both the Sazerac and Cocktail à la Louisiane. The cocktail bears a resemblance to my After-Dinner Manhattan from a few years back, which I designed for a customer who was craving coffee in her nightcap.

The Sazerac is an institution and I love the rye-based versions dearly. But I also like split-base recipes that recognize the Cognac roots of the cocktail (and Cognac-only versions too!). This version of the Sazerac plays up the cocktail’s “Improved” qualities, splitting the aromatic ingredients between four different products, as well as splitting the base.

Ever since I wrote a piece for PUNCH about the Roffignac, I’ve wanted to develop my own spec. Though we’re taking a bit of a shortcut with this method and not making our own shrub, the à la minute “shrub” works and I love the way the plum and Cognac go together. A great drink for September that straddles summer and fall.

I wanted to demonstrate a fancy application for our Club Pimm’s, and I immediately thought of doing a Pimm’s Cup Royale, i.e. topped with Champagne. I also wanted to integrate some of the traditional fruit and mint that are used in Pimm’s Cups and decided a Cobbler format would be the perfect vehicle. Served over crushed or pebble ice, our Pimm’s Royale is, naturally, garnished with abandon.

Here’s a fun serving suggestion for our homemade Club Pimm’s and our cucumber-lemon shrub: a do-it-yourself Pimm’s bar for your next gathering! I’m happy to say that this concept caters to drinkers and non-drinkers alike, so everyone will feel taken care of at your spring (or summer!) soirée.

I see our Club Pimm’s as a pre-batched cocktail, apéritif, and digestif all in one. It occurred to me that, served in the style of amaro caldo, it would make an excellent, warming beverage for a chilly evening or a rainy Sunday afternoon–both common in April where I live. Adjust the recipe below to suit the size of your serving vessel.

I’ve long dreamt of creating my own homemade Pimm’s. The original Pimm’s No.1 is great, but I wanted to come up with something with pronounced bitterness, more body and oomph. I’m really excited about what I came up with–it is both a complete standalone cocktail and an excellent ingredient in mixed drinks.

There are several pre-Prohibition era drinks that bear the name “Blackthorn,” “Black Thorn” or “Blackthorne,” hence the numeral after the title. This version takes some of the ingredients from the English (gin and/or sloe gin) and Irish (Irish whiskey) versions and applies an equal parts structure. An optional barspoon of peaty Scotch makes this Manhattan cousin slightly smoky, if that’s your thing.

The Martinez and other early “Martinis,” were a lot like the first Manhattan recipes. Many such recipes called for a 2:1 ratio of vermouth to gin–which you are welcome to try! I went with 1:1 here. The gin, of course, would have been in the sweetened Old Tom style or Holland gin, aka genever. Lemon is traditional, but I went with an orange twist, wrapped around a cherry for visual interest.

I’m challenging you all to come up with your own house Manhattan; or a new favorite Manhattan; or your fall 2021 Manhattan! Whatever you’re seeking, I hope these guidelines help you find it.

Apple brandy Manhattans are one of the most delicious (and fall-appropriate) branches of the family tree. We have a great triumvirate here: the dry Star (Harry Johnson, 1900), the sweet Star (George Kappeler, 1895), and the Marconi Wireless (Old Waldorf Astoria Bar Book, 1935).

The Manhattan was a disparate, but powerful, force for the first thirty or so years of its existence. In the years just before Prohibition, and through the ‘30s, the recipe begins to solidify its 2:1 ratio, the bitters overwhelmingly Angostura, and the garnish is usually a cherry.

The earliest versions of the Manhattan resemble quite closely the original Cocktail (spirits, sugar, water, bitters) and feature a split base of rye and Italian (sweet) vermouth. This is an excellent example, taken from the second edition of Harry Johnson’s Bartenders’ Manual.

This is the cocktail I came up with on the spot during our September 2021 video shoot when I realized I hadn’t developed a recipe to use as the example for the Manhattan Challenge. Love it to this day and still make it!