59 W. 44th St., nr. Sixth Ave.; 212-840-6800
The Legend: William Faulkner said, “Civilization begins with distillation,” but his behavior was far from civilized at this hangout of Sinclair Lewis, H.L. Mencken, and Edmund Wilson. According to Bailey, Sherwood Anderson had to be called to stop the “drunk out of his mind” Faulkner from running around in his underwear.
The Liquor: Imitate Anderson with an old-fashioned, swig mint juleps like Faulkner, or fall in love with a champagne cocktail as Round Table founder Dorothy Parker did.
86 Bedford St., at Barrow St.; 212-675-4449
The Legend: As book covers lining the walls attest, drinkers at this West Village speakeasy have included Djuna Barnes, Robert Benchley, John Cheever, Ring Lardner, Edna St. Vincent Millay, Dorothy Parker, John Steinbeck, James Thurber, and F. Scott Fitzgerald. According to owner Steve Shlopak, the Fitzgeralds topped off their wedding party at the Plaza with a day of drinking at Chumley's and consummated their marriage in one of the booths.
The Liquor: Follow the example of Fitzgerald (who said, “First you take a drink, then the drink takes a drink, then the drink takes you") by ordering a gin rickey. Or get hammered on rusty nails (scotch and Drambuie), the instruments of intoxication favored by Cheever.
57 E. 55th St., nr. Madison Ave.; 212-751-7272
The Legend: If the account in the bartending guide is correct, sportswriter Ring Lardner took full advantage of his time at the Friars Club staying for 60 consecutive hours. “The story went that he went there to drink and just kept drinking,” says Bailey. “His reason for leaving was that someone had come over and started to tell him a joke. He just thought the guy was a bore, and so he got up and left.”
The Liquor: If you find a way into this members-only club, make it a Manhattan in honor of the whiskey-drinking Lardner. But unlike the columnist, know when to call it a night.
915 Third Ave., at 55th St.; 212-317-1616
The Legend: Though it was filmed in California, Billy Wilder’s The Lost Weekend used a bar modeled on P.J. Clarke’s. “While they were shooting it, [actor] Ray Milland said this guy would walk onto the set at five o’clock every afternoon and put down two quarters on the bar and order a whiskey,” Bailey says. “It turns out it was Benchley, who was out in L.A. and was homesick. He just wanted to be back in P.J. Clarke’s.”
The Liquor: James Jones, a frequenter of the actual P.J. Clarke's said, “It is a far, far better thing than we have ever done to be disciples of Bacchus rather than of Christ." Those toasting the sentiment should do so with his signature Singapore sling.
21 W. 52nd St., nr. Fifth Ave.; 212-582-7200
The Legend: “Drinking makes such fools of people, and people are such fools to begin with, that it’s compounding a felony,” Robert Benchley once stated. According to Bailey, the New Yorker drama critic (whose table 3 is marked by a brass plaque) demonstrated this dictum when he asked a man outside of the '21' Club to call him a taxicab. When the man informed that he was an admiral for the U.S. Navy, Benchley retorted, “‘Well, then call me a battleship.’”
The Liquor: At the age of 31, Benchley's first cocktail was an orange blossom (“basically a Screwdriver with gin,” explains H&B's). Another recurrent visitor, John O’Hara, mentions the fruity planter’s punch in his novel Butterfield 8. Perhaps he was under its influence when he literally punched out a dwarf.
White Horse Tavern
567 Hudson St., at 11th St.; 212-243-9260
The Legend: The bar is most associated with Irish poet Dylan Thomas, who reportedly had his last drinks there. But Jack Kerouac, who also frequented Kettle of Fish and Cedar Tavern at their old locations, was said to visit the White Horse as well. According to Bailey, the words "Kerouac, go home" were scrawled above the bathroom urinal, so that he would remember to stop drinking and go home.
The Liquor: The Beat writer advised the following: “Don’t drink to get drunk. Drink to enjoy life.” Do so Kerouac's way by asking for a margarita.