This riff on the classic Sidecar is more sultry than sour -- it’s a dream pairing of good cognac with dark creme de cacao along with the nuttiness and caramel of a deep tawny port. Lime juice and chocolate bitters brighten and lighten the richness, making it less of a dessert and more of a dignified, delicious tease.
The History of the Chocolate Sidecar
On one hand, we can look all the way back to the Crusta Cocktail of the 1800s, or the Sidecar of the 1920s, to strip this drink down to its elements: A classic sour cocktail made with cognac, fresh citrus, and a touch of sweetness.
On the other hand, you have the modern legend Wayne Collins to thank for this cocktail. Collins created this 2005 riff on the classic by substituting both creme de cacao and tawny port for the curaçao in the typical Side Car. A discreet amount of lime juice is the perfect bright balancing point for the richness of the chocolate and port, and the complexities of the cognac. (Orange juice would also be an inspired substitute – replacing both the orange flavor and filling in for the citrus.)
The Best Cognac (or Brandy) for this Cocktail
If you’re just starting out with your home bar, you may well have a bottle of brandy on hand, but nothing labeled Cognac. So what’s the difference between the two?
Cognac is brandy -- a distilled spirit made from fermented fruit juice (typically grapes). But cognac is to brandy what Champagne is to sparkling wine: typically better quality, with more complexity and elegance. Its grapes must come from the Cognac region (similar to Armagnac, another fine brandy), and the white wine from those grapes shall have no added sulfites.
Look for VSOP Cognac, a designation indicating it has been aged for at least four years, but still entry-level in price and perfect for cocktails. Remy Martin VSOP and H by Hine VSOP are both great choices.
The Best Port for this Cocktail
Port is a sweet, red, fortified wine typically from Portugal (look for “Porto” on the bottle’s label). Is it typically enjoyed as a dessert wine? Indeed it is. But does its luscious, sing-songy, caramel, spice, and hazelnut notes have to be confined to those late-evening hours, enjoyed alone and never paired up? Not if you have the right match in mind.
We could talk all day about the various types of Port and what distinguishes them, but for our purposes here – what best complements the chocolate and adds to the cognac – look for Tawny and Ruby ports. While they have much in common, tawny ports gain toffee and caramel colors, nutty flavors and hints of clove and cinnamon from their aging in wooden barrels. Take that into consideration and you can just imagine how well it pairs with chocolate.
Graham's 10 Year Old Tawny Port is a personal favorite, with its richness and full, nutty bouquet giving way to a rolling finish. It is rich enough to hold its own with the creme de cacao, without nullifying the finery of the cognac.
An interesting substitution for Port would be Sherry, a kissing cousin from the Jerez region of neighboring Spain. Drier and sharper than sweet port, without the dark berry, a dark Oloroso sherry, like Lustau’s, has more concentrated nutty and dried fruit flavours.
A Word on Chocolate
It’s said that the only time chocolate should appear in a cocktail is in the form of bitters: a few drops at a time as a ... suggestion. That is pretty much how it shakes out, but there might be exceptions made. And this is one.
While nearly every chocolate cocktail you will come across is a monstrous concoction better served as an actual layer cake, this Chocolate Sidecar doesn't play those chocolatey notes so heavily that it’s more dessert than proper drink. The chocolate in the crème de cacao plays well with the port, and together they provide a rich, harmonizing line beside the Cognac.
A dark Créme de cacao like Drillaud, DeKuyper, or Tempus Fugit Crême de Cacao à la Vanille, would play well and keep the right balance of sweetness and richness.
Your last word with regard to chocolate is your dash of bitters. Whether homemade or Fee Brothers Aztec Chocolate Bitters, you’ll be adding more dimension to your other flavors while giving just a bit of edge to your chocolate. It’s a dispensable touch, but just barely – you will be better served by adding it.
Fresh Lime Juice is Best
We’re specifying – outright recommending – fresh lime juice here, but you could go with a bottled lime juice if it’s what you have on hand. There is a difference, but you’ll still end up happy.
If you have a sweetened lime juice like Rose’s on hand and want to give that a try, omit the simple syrup called for.
Variations on the Chocolate Sidecar
- Coco-late Sidecar: Add 1 tablespoon of a house-made coconut cream (4 parts Coco Lopez coconut cream stirred into 1 part unsweetened coconut milk).
- Use a dark, aged rum (or tequila) in place of the cognac.
- Cocorange Sidecar: Replace the lime juice with a freshly squeezed orange juice.
More Cocktails to Try
- Chocolate Lark (Low-Proof)
- Brandy Alexander
- White Russian
- Grasshopper Cocktail
- Brown Sugar Irish Coffee
Take a pre-chilled glass and run a wedge of lime across half of the rim. Wipe off any drips, and then roll the edge of the glass in a saucer containing some combination of chocolate powder and freshly grated dark chocolate.
Make the cocktail
Add all ingredients to a cocktail shaker, fill with ice and shake until chilled. Strain into a chilled coupe or martini glass.