Grit and Grub in San Francisco’s Tenderloin

Grit and Grub in the Tenderloin (cont.)

Any discussion of the Tenderloin would be null and void if one failed to pay respect to the neighborhood dives. Everybody has his favorite, and the names are as colorful as the people inside: the Ha-Ra Club, Cinnabar, the Gangway, the Brown Jug. Here are three more casual joints we like.

There are also a couple of great high-end cocktail lounges in the neighborhood, for when you’re feeling fancy. They are listed below.

CASUAL

  • 21 Club
  • 98 Turk Street
  • 415-771-9655
  • Open daily 10 a.m. to 2 a.m.

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Recently outed by Esquire magazine as one of the best bars in America (a bit of an overstatement), the 21 Club is still the most classic dive we can think of. It offers no beer on tap, and you will not find a microbrew or even a midtier whiskey like Jameson’s on the menu. You will find, however, Miller High Life in bottles, plus an altar to Spam behind the bar. Slip a dollar into the jukebox, put on some Merle or Mick, and zone out on the two big picture windows as seedy life in the lower ’Loin goes by. (It’s definitely best to come during the day, and if you’re a woman, bring a male escort.) You’ll have plenty of company: There are always lots of people drinking here, even before lunch.

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  • 222 Club
  • 222 Hyde Street
  • 415-440-0222
  • Open Tuesday through Saturday 6 p.m. to 2 a.m., closed Sunday and Monday

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A little grimy, with exposed brick and glowing red lights, the 222 Club is where the twentysomethings come to dance and get their drink on. At the packed, narrow bar, house-made pizzas are served until midnight alongside $2 PBRs and stiff mixed drinks. If you can make it through the crowd and down the stairs, you’ll find an underground dance floor reminiscent of high school parties in someone’s basement. The music varies on any given night, from hip-hop to grime to drum ’n’ bass, with electro, house, and booty funk thrown in. It’s not unusual to hear lyrics yelled in unison and see arms in the air and a sea of bodies morphing into one giant undulating mass. Yes, hookups abound. Two of the most popular parties held here are “Lights Down Low” (second and fourth Friday of the month) and “No Fucking Requests Ever” (third Friday of the month). Don’t worry too much about what you wear—it’s so damn hot downstairs that most of it’s bound to come off anyway.

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  • Whiskey Thieves
  • 839 Geary Street
  • 415-409-2063
  • Open daily 5 p.m. to 2 a.m.

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Whiskey Thieves is not a real dive, because real dives don’t have 25 Irish whiskeys behind the bar and plenty of Scotch and bourbon to boot. But it’s got that grungy rock ’n’ roll feel: Bob Dylan’s Desire blasts from the speakers, and a blanket of cigarette smoke envelops you as you enter (it’s one of those few owner-operated joints where you can still smoke inside). You’ll have to squeeze around a frenzied pool game to curl into a back booth. Attracting a neighborhood crowd of night owls in their 20s and 30s with expensive haircuts and thrift-store clothing, the bar’s hopping even an hour before closing on a Tuesday night. People are in it to win it: tables of kids doing shots, draped all over each other, fedoras askew, gleaming with a faint sheen of sweat in the weak light.

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FANCY

  • Bourbon & Branch
  • 501 Jones Street
  • 415-346-1735
  • Open Monday through Saturday 6 p.m. to 2 a.m., closed Sunday

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A modern-day speakeasy with a real former Prohibition-era speakeasy beneath it (the owners found it—brass bell alert system and secret exits intact—when they bought the bar), Bourbon & Branch looks like a Hollywood depiction of the 1920s. It’s all red velvet flocked wallpaper and antiques, including a working gramophone. The rooms are ultra-ultra-dark, lit only by flickering candles, and Jelly Roll Morton plays softly in the background.

This is where many an ambitious “bar chef” comes to launch his or her San Francisco career. The drink selection borders on overwhelming, with page after page of cocktails, including classics like the Sazerac ($11), new creations, and daily specials like the Rum Crawl ($11), consisting of rum, house-made Falernum (lime liqueur), ginger syrup, lime juice, whiskey barrel–aged bitters, and a seared orange peel garnish. There are also 50—yes, 50—different bourbons, all served with linen napkins.

The main room works on a reservation system, accessible via the website; when you go online you’re given a password to use when ringing the locked front door (ours was “viper”—the password changes nightly). This practice keeps out Tenderloin riffraff and creates an air of taboo. There’s also a no-reservations-required room in the back, known as the Library, for which you utter the password “books.” (You may be wondering why you need another password when you could just say “books” every night and get in. Well, yeah—there are some things about this bar that are a little precious.) To enter the Library, you pass through one of those revolving bookcases that you see in the movies. Oh, and there’s no sign out front saying “Bourbon & Branch.” Instead the sign reads “Anti-Saloon League.”

Reservations are often booked a month in advance, particularly for Friday and Saturday nights. But Bourbon & Branch is best avoided on these nights anyway, when the crowd can get a little bridge-and-tunnel (boys on dates pounding Red Bull before entering, with popped collars and majorly buffed upper bodies). Better to come on a weeknight, when you and a few gay guys and restaurant industry types can have the undivided attention of the bartender as he tastes, pours, shakes, swivels, and incinerates, like a boozy alchemist.

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  • Rye
  • 688 Geary Street
  • 415-474-4448
  • Open Monday through Friday 5:30 p.m. to 2 a.m., Saturday and Sunday 7 p.m. to 2 a.m.

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You would walk right past Rye if you weren’t looking for it: Only a discreet wood-panel wall announces its presence on the block. Inside is a relaxing lounge, with exposed brick walls, concrete floors, low seating, and tasteful, modern paintings: a little bachelor pad–like. Cocktails, $9 each, are the centerpiece: standards like the Dark ’n’ Stormy (dark rum and ginger beer); twists on classics, like the signature basil gimlet (vodka or gin, lime juice, fresh basil, and raw sugar); and new inventions like the Flash (gin, kiwi, cucumber, and lemon).

One Monday a month, Rye hosts an Iron Chef–style competition for local bartenders, in which they see who can make the best drink out of a specific spirit. Patrons taste and pick the winner—for free.

The crowd can get a little cheesy later in the evening: uninspired partyers looking to pick somebody up, and on weekends, big, big crowds. But Rye is mellow and perfect for an early classy cocktail.

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