Cocktail Guide for reference, I texted my friend Tim to…">

Drinking Like a Mad Woman

Do you ever put down the remote after the latest DVR’d episode of Mad Men and think, “I could use a drink?” I do, especially after this week’s installment, in which Don Draper proved yet again that unforgivable cads can brood and charm their way out of anything. After a quick glance at AMC’s Mad Men Cocktail Guide for reference, I texted my friend Tim to…

Do you ever put down the remote after the latest DVR’d episode of Mad Men and think, “I could use a drink?” I do, especially after this week’s installment, in which Don Draper proved yet again that unforgivable cads can brood and charm their way out of anything. After a quick glance at AMC’s Mad Men Cocktail Guide for reference, I texted my friend Tim to meet me in the Palm Court bar at The Drake. The gold-banistered staircase and huge flower arrangements there remind me of the Mad Men Valentine’s Day scene in which Don watches a luminous Betty descend into the dining room of New York’s now-shuttered Savoy-Plaza Hotel. 

In keeping with the evening, I decided to turn on the Draper-inspired charm and chat up our fellow barflies. Two other patrons were cozied up to the bar: Paul, a 30-something suburbanite who was downtown on business and displayed extreme suspicion with regard to my note taking (“This is not a Dateline special,” I reminded him more than once), and Cheryl, a vivacious fashion consultant from Martinsville, Virginia (“We’re known for our NASCAR track and having once been the sweatshirt capital of the world,” she explained). Cheryl and I, it seems, were destined to be friends: “You’ll never believe this, ya’ll,” she told our motley group. “But a psychic told me in June that an Amalie would soon come into my life!”

Tim and I ordered an Old Fashioned and a Tom Collins (both $14) from the smiling bartender, Thawt, who appeared stumped. “An Old Fashioned? What’s that?” he asked. “I come here from Thailand in ’91. I need English 101!” I had a feeling Thawt was yanking my chain, so when he set the perfect pink concoction in front of me, I asked what was in it. “Who knows?” he giggled. “I made it with my eyes closed!” Thawt eventually got serious and ran down the list of ingredients, which included muddled cherries and Jim Beam (the Old Fashioned), and gin with sour mix (the Tom Collins). “Sorry to interrupt,” said Tim, who had spaced out during the shoptalk. “But can we please discuss the new Black Eyed Peas song? I mean. Bam.” Tsk, tsk, Tim: so anachronistic for our 1960s night out.

Paul graciously picked up the tab before disappearing with a lady friend, while Tim, Cheryl, and I proceeded down the street to The Drawing Room at Le Passage, a spot known for its studious approach to classic cocktails. For compare-and-contrast purposes, I ordered another Old Fashioned ($12). Master Bartender Timothy presented me with a dark, potent drink made with Old Overholt Straight Rye Whiskey, which—no Mad Men novice himself—he pointed out made an appearance in this season’s “My Old Kentucky Home” episode. (“There’s no bourbon here,” Don said to Conrad Hilton at a country club Derby party. “How do you feel about rye?”)

As a native Kentuckian, I was especially pleased—but that was nothing compared with what came next, when the man sitting next to me at the bar mentioned he was personally acquainted with Jon Hamm, a.k.a. Don Draper. “I’m on the board of an arts organization in St. Louis, and he was the honorary chair at our gala this year,” he said. With the coincidences piling up at an alarming rate, we decided to ask for the check and call it a night. One more glass of muddled cherries, and who knows? I just might start wearing pointy bras and curling my hair in a flip.

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5 years ago
Posted by DMR

I recently ordered an Old Fashioned in a hotel bar. The bartender assured me that he knew exactly what was involved in said cocktail, then proceeded to ask me what kind of sherry I would prefer. Even Don Draper couldn't make that work.

5 years ago
Posted by Kate Brennan

The Drawing Room is my undeniable favorite for an Old Fashioned or Manhattan. The Bristol in Bucktown also makes a mean Moscow Mule, served in an old-style copper mug and sure to transport you back in time.

5 years ago
Posted by KAC

Hub 51 is a big hot spot for ad execs these days. Maybe the Don Draper of today hangs out there? I wouldn't complain if I spotted his reincarnation...

5 years ago
Posted by Chi-York

Great read.

While MadMen may have captivated a nation to start drinking at 9:00 a.m. and smoke indoors, your article certainly made us all feel a little special for having these drinks and establishments at our fingertips. It is nice to know that I am not the only who feels like wearing pencil thin ties, and going out on the town to slam some classic cocktails of a time since past.
Check out Monk's Pub on Lake right under the L tracks in the loop. A number of modern-day ad execs go there, but they all drink the house beer because budgets in the industry have bottomed out and no one can afford fine spirits anymore.

5 years ago
Posted by Amalie

Thanks, Chi-York! I've always heard about Monk's but have never been there. I'll have to go and order myself a nice PBR in lieu of the golden age-favorite Tom Collins.

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