I've always loved novels where characters drink their way around a town from page 1 to "THE END"--a few favorites: "The Pint Man," "A Fan's Notes," and "The Thin Man"--and I wanted to write a drinking-at-bars novel of my own.
Stu Fish does a ton of drinking in my book, the majority of it in New York City, and many of those places are real, or at least based on places that are, or were, real.
Thus, a literary drinking tour of all the places Stu tipples at in "How to Fail: The Self-Hurt Guide":
Le Enfants Magnifique (pg 11) -- The un-hip French restaurant where Stu's successful friends fete him on his 30th birthday and where he has no choice but to drink expensive "Wine Spectator"-recommended wine ordered for him. Based on the bland Cafe un duex trois on West 44th Street.
McManumus's (pg 14) -- A "plastic Paddy pub" Stu is frequently forced to drink at when no other options are available. Based on any number of cookie cutter ersatz Irish bars in Midtown which serve $8 Guinness pints and have bored Irish bartenders who look like they would have never come to America if they knew they'd have to waste their days working at inauthentic pubs that Manhattan's after-work crowd loves for some damn reason.
Marriott Marquis's Bar (pg 44) -- Where Stu and girlfriend Ash have a quick drink before meeting up with Stu's visiting Midwestern parents. Based on the Atrium Lounge which, surprisingly, for a tourist trap hotel bar in the middle of Times Square, is not half bad. Yeah, it's filled with rubes wearing XXL t-shirts of their hometown college team ("Roll Tide!") and sparkling white Reeboks, but if you're in a pinch for a drink before meeting some unadventurous visitors, it's not awful.
FonDo's and Don'ts (pg 49) -- The "14 out of 30" Zagat-reviewed restaurant where Stu, Ash, and Stu's parents dine and Stu drinks a "Staten Island Iced Tea." Completely non-existent in Manhattan (shockingly), it's based on the Melting Pot which is an overpriced chain fondue place located in shopping malls in other cities and, actually, isn't half bad. It's hard to fuck up a hot vat of cheese though.
The Wee Pub (first introduced on page 87) -- The main drinking spot in "How to Fail" with its gimmicky over-sized bar, stools, drinks, and even bartender (the 6'7" Irishman Lynn). Where Stu immediately heads after he gets laid off, where he goes for months straight in a drunken malaise after getting dumped by Ash, where he met his best friend (the "Lesbian Wingman" Bonnie), where he picks up numerous girls (notably, his brief girlfriend Katie), hangs with the guys, gets loaded, and watches his beloved Knicks on TV. Based on a place formally called The Wee Pub on 9th Avenue in Hell's Kitchen (since remodeled, un-Wee'd, and renamed The Snug).
Ruby Tuesday's (pg 123) -- Where Stu has a most unfortunate lunch with Ash's family after she competes in a marathon in New Jersey and is forced to drink giant 32 oz frozen mugs of macro beer. Like any chain restaurant in the middle of the 'burbs it's not awful, just boring, but this author still prefers Chili's personally (delicious margaritas and queso).
J. Monroe's (pg 126) -- The beloved local haunt of Stu and Ash back when the going was good and happy hours always ended up leading to the bedroom. Based on an UWS joint called McAleer's which does indeed have great wings and terrific pitcher deals.
Harry's Conundrum (pg 133) -- Where Ash celebrates her birthday with a party that goes tragically wrong for Stu. Based on an UWS dump called Jake's Dilemma that is always filled with youngish twentysomething bozos bumping into you.
Boffo Bar (pg 158) -- The UWS bar Stu heads to after Ash dumps him and where he picks up an annoying one-night stand. Based on the very cool Dive Bar on W. 75th Street.
"Real" dives (pg 175) -- Stu always finds himself trying to tell people that they don't drink at dive bars, but that they drink at "faux"-dives, places set up to be crappy yet still safe for yuppies wanting to a verisimilitude of "slumming it." The real dives in "How to Fail," though, are based on numerous spots between 10th and 12th Avenue in Hell's Kitchen (most notably J. Mac's Lounge) which you've never been to because you're a pussy.
Times Square Applebee's (pg 213) -- A favorite "bar" of Ash's that Stu was always forced to drink at to appease her. One of the things he most revels in after being dumped is never having to drink at a boring chain restaurant again.
Rudy's (pg 230) -- The site of the bulk of Footchapter 9 ("How to Fail in Bed"), where Stu takes a first date to enjoy cheap pitchers and free hot dogs. The iconic Hell's Kitchen dive (pictured above) is a longtime favorite of this author and is, quite frankly, probably now more of a "faux"-dive itself. Especially considering the bar has a beautifully designed website featuring its own theme song (!).
Different kinds of bars -- From page 245 to 249 Stu lists the countless kinds of bars in this world (from dive to hotel to lesbian to airport bar, etc) and the various kinds of women one will meet there.
Hollywood nightclub (pg 274) -- When Stu visits his successful screenwriting buddy Wesley in Los Angeles, he is taken to a cheesy Hollywood Boulevard nightclub infested with quasi-celebrity douchebags. Based on idiotic places I've only seen on reality shows.
Size 2 Lounge (pg 295) -- An upscale spot "ironically full with a bunch of size 22s." Based on every single lame Meatpacking District bar in Manhattan.
I just hope "How to Fail" is famous enough one day that plaques hang in all the above-mentioned bars and people actually set up their own pub crawls and a giant statue of Stu Fish is erected in front of the site of the Wee, just like the Ignatius T. Reilly statue in New Orleans.