David Wondrich is a little ticked. An expert mixologist and the author of Esquire Drinks, Wondrich is relating a Maxim article from last year suggesting that lads “retire” the manhattan cocktail and replace it with a bourbon drink mixed with Gatorade Ice Orange and grape jelly. We enjoy a collective gag: Gatorade? Lucky for Liquid City, Wondrich has agreed to take manhattans with us, discussing the pros and cons of their various incarnations (the standard is two parts rye whiskey, one part sweet vermouth, and two dashes of bitters, topped with a maraschino cherry or orange twist), and why he calls it “a more affectionate cocktail than the stand-offish gin martini.”

The tasting begins at the WHISKEY WARD (121 Essex Street, 212-477-2998), the inexpensive but handsome Lower East Side drinking hall specializing in bourbon and brew. According to Wondrich, rye whiskey is the most important factor in making a good manhattan. The problem is, rye can be incredibly difficult to find: It was traditionally made in the Northeast until the industry virtually vanished during the last century, although a few boutique distilleries have recently sprung up. Good thing Van Winkle rye is on offer at the Ward, so we forgo the bar’s manhattan made with Maker’s Mark bourbon and spiked cherries ($8)—a frivolous confection that’s as laughable to a hardcore manhattanite as a cosmopolitan is to a martini man. But Van Winkle is such good rye, it’s almost a shame to dilute it with vermouth and such. We do so anyway, and the drink ($9.50) is like a prizefighter who’s taken one too many punches—the mellowed toughness betraying a sweetness that leaves you just a little sad.

A younger and therefore less concentrated and syrupy rye would have yielded a preferably spicy potion, says Wondrich, so it’s off to the tony BEMELMANS BAR (Carlyle Hotel, 35 East 76th Street, 212-744-1600), famous for its fanciful murals and for shaking some of the stiffest (and most expensive) cocktails in town. Audrey Saunders, the Carlyle’s new beverage director, who’s helping the classic bar shed its stodgy image, is on hand to greet us. A self-professed “cocktail geek” with boundless energy, Saunders informs us she’s out of Sazerac rye, and after some heated discussion, it’s decided we’ll have Booker’s bourbon, bottled straight from the barrel by Jim Beam’s grandson. The benefit of hanging out with cocktail geeks is that you get to try out all sorts of inventions: Saunders happens to have Gary Regan’s Orange Bitters behind the bar; Regan, a noted cocktail writer, has convinced a distillery to bottle the defunct recipe. The resulting manhattan ($18.75)—its dividends (the extra that’s left in the shaker) poured in a glass and set to ice—seems more grown-up than the one at the Ward, and at 125 proof, it’s got plenty of bite, not to mention manly orange zest.

Having sampled the work of whiskey experts and high-end cocktail specialists, we were eager to check out what was shaking at the local dive. We set off for Park Slope’s fabled O’CONNOR’S (39 Fifth Avenue, Brooklyn, 718-783-9721), where the hipsters enjoy drinking beer, not martinis. Like most bars, O’Connor’s doesn’t have rye on its shelves, so we asked Bart the bartender to make our manhattans with John Powers Irish whiskey, occasionally referred to as an Angelo & Mike (from the pairing of Italian vermouth and Irish whiskey). It seems an appropriate outer-borough cocktail, and Bart stirs us up a batch, pouring the light, smooth potion ($6) into old-fashioned parfait glasses. “A pleasant tipple,” declares Wondrich. Agreed.