Really simple and really good! Skip the soda, and can also be shaken and served straight up. I built mine over ice as suggested, but subbed flavored soda with seltzer/club soda. Any way you do it, you can't screw it up and it's a crowd pleaser.

Does need a bit of sweetener (e.g. the lemon-lime soda) - tart if this is absent.

Made it with a random cheapo gold rum and allspice dram instead of the bitters. It's good! Would be great over crushed ice.

My variation:

1 1/2 oz Rye

3/4 oz Amaro Nonino

1/2 oz Amontillado (dry)

1/2 oz PX

1 dash Regans'

Very nice indeed.

This can be found on page 206 of the Death & Co book, credited to Alex Day (2009).

Curated to add attribution and reference, thanks!

The Cocktail Virgin post calls for 1/4 ounce of maraschino. That change made a big difference for me.

The Cocktail Virgin post calls for 1/4 ounce of maraschino. That change made a big difference for me.

Curated to change the 1/2 oz. maraschino to 1/4 per link.

OK, but I would half the vermouth. Very sweet with the stock proportions.
I prefer https://kindredcocktails.com/cocktail/black-lodge (which we make with Maraschino) for this type of drink.

Didn’t have 100 proof on hand. Metric shows 1 cl and 1/4 oz closer to .75 cl. (incorrect conversion?)
I put 1 cl of Maraschino and for the others 5/3/2 cl (1oz Cocchi) and still too sweet. Maybe add bitters? I had 2 olives.

The units conversions between metric and English units can be problematic. The idea seems to have been to default to increments available in more conventional metric or U.S. bar equipment, but the result is that the proportions can be altered when using units other than the system the cocktail was entered in (or vs. the source reference.) In this case the source is a U.S. recipe, so the metric conversions are .25 cl high both for the Cynar and the Maraschino. Both are fine in English (U.S.) units, so when in doubt, toggle the unit choice in your account to match the way it was likely entered, and/or check the source. Curation note: I have updated the reference to a direct link to the cocktail.

Chocolate martini without it being some gross, sugary mess like you'd normally get if you asked for that? I'm down

So I went looking for this drink, and it seems to be 1906ish, but it's equal parts Tom Gin and dry vermouth plus some orange bitters. Anyone have the original Imbibe to see if the cocoa is a Wondrich thing? Thanks,  Zachary

FWIW this Wondrich Esquire bit from 2007 makes no mention of cacao in connection to the Racquet Club. (And it also suggests equal parts, and an orange rather than lemon twist.)

Wondrich's book, Imbibe! notes the Cacao discrepancy in Kappeler, and uses as a source the New York Sun, 1893. Without seeing the particular article, it is hard to tell. I haven't seen the 2011 Imbibe article where Wondrich provides the Racquet Club Cocktail recipe either, but the Imbibe! book's recipe is somewhat anachronistic, using Plymouth gin (even it if was gin made in Plymouth, wouldn't an Old Tom be closer to the style at the time or was Plymouth gin dry by then?) It also is a 50:50 (rather than shown in the recipe on this site.) Wondrich's ingredient notes say, "Use an Italian vermouth" rather than dry vermouth as given here and by Kappeler. So I am not sure what has happened but something seems mixed up. Was "French vermouth: intended rather than "Italian?" I dunno, but it makes a nice cocktail with Plymouth, Regan's orange bitters, and Tempus Fugit Creme de Cacao using a mild red vermouth such as Dolin Rouge.