I need a fedora. I recently toured the city's most storied, hallowed halls of gin joints, speakeasies and nightclubs, transporting myself to a different era one sip at a time. Rather than downing another round of choco-tinis, sake-grias or other Frankenstein-esque drinks, I recommend that you too drink something new, er old. Okay, maybe "vintage" works best here. Slinging everything from Old Fashioneds to Manhattans, these keepers of the cocktail flame will give you a taste of another age.
An Old Fashioned at Coq d'Or
Knowing that the Drake Hotel has served a number of presidents, royals, celebrities and other high rollers, going to the Coq D'Or felt more than a little intimidating. Dark, leather-clad and extremely intimate, this one-of-a-kind bar in the super-swanky hotel knows its old-school cocktails.
Sitting at the bar with a number of tourists, I ordered an Old Fashioned on the rocks. When the bartender asked for my bourbon preference (Maker's Mark, thank you), I realized I was in the presence of true professionals. He muddled oranges and cherries with bitters, topping it off with bourbon and soda water for a sweet, tart and smoky concoction. Though the cuisine was slightly more low-brow than I anticipated (nachos and sandwiches), a trip here wasn't cheap: My Old Fashioned set me back $12.
Tom Collins at The Pump Room
It's easy to imagine Sun-Times columnist and bon vivant Irv Kupcinet lording over this grand eatery in its heyday. The large wraparound bar looks out onto the dining area, where you can picture dozens of tuxedo-clad diners daintily chewing on roast pheasant while a jazz combo tootles deep into the night. With walls plastered in black-and-white photos of celebrities, the bar would make Billy Crystal's "Fernando" feel right at home. (Geesh, even the references in this piece are old.) I had a date with a Tom Collins, though, and after shelling out $8, a new appreciation for gin.
The bartender mixed Bombay gin, soda water, lemon juice and simple syrup, and garnished the almost-tropical-like concoction with a lime. It tasted breezy and light, citrusy and sweet, a flavor profile that an enterprising bartender could likely rebrand as a hyper-trendy gin-gria or something. But "Tom Collins" was good enough for me.
A Manhattan at Matchbox
Not every cocktail on this list has to be imbibed in swanky digs. Sometimes a good drink is best consumed in close company, and it's hard to imagine any place where space comes at more of a premium than Matchbox. If you want to try one of its legendary Manhattans, treat the Matchbox, with a legal capacity of just over two dozen, like I did: showing up early. I like to get in during daylight hours, which might be indicative of a problem, but it's often the only way to get a little breathing room for me and my drink.
With a history dating back to the 1800s, the Manhattan, made with bitters, bourbon, vermouth, cherries and a little cherry juice, is classic to the core. To make it even more of a treat, Matchbox adds its signature, brandy-soaked cherries. Imported from France and saturated for five years, these babies have a rich sweetness unrivaled by maraschinos straight out of a jar.
The cocktail had a deep, masculine taste, like the memory of a pipe-smoking grandfather. This libation comes straight up or on the rocks, and it shouldn't be missed, especially since it'll only set you back $6.50 with Jim Beam. My preference, straight up with Maker's, raises the ante to $7.
A Brandy Alexander at Green Mill
On the last stop in my trek through time, I left it up to chance. Jazz and the cocktail culture both came of age during the Prohibition Era, and there's no better stop for recapturing this scene than at one the most famous bars in town—the Green Mill. The bartender presented me with a list of heretofore unmentioned and unconsidered cocktails from a bygone age, like the Stinger, Grasshopper, Gin Fizz and Rob Roy. I settled on a Brandy Alexander, not knowing even what was in it. It certainly sounded old to me, and it dates back to the early 1900s.
As it turns out, it was the sweetest and thickest drink I tried. Made with brandy (of course), Creme de Cacao and heavy cream, this milkshake-like concoction is not a drink you can pound all night. (A so-old-it's-hip-again pint of Pabst is better for that.) Rather, it's a cocktail to sip on the veranda after dinner, maybe over a couple hands of canasta. And at $6, the price was almost as old-school as the cocktail itself.