Entertainment and clubs
222 Club
In the 50s and 60s this used to be a famous jazz club called the Blackhawk. Today it is a cutting edge underground venue with DJs and live music. The Blackhawk was actually at 200 Hyde St, which is now a parking lot.
Aunt Charlie's Lounge
If you haven't already guessed from the name, "Aunt Charlieâs" is a transvestite dive bar. It hosts a wide variety of entertainment shows and drag shows that are popular with gays, lesbians, transsexuals, and indeed straight patrons. Cheap, stiff drinks accompanied by endearing, harmless, and vocal co-drinkers, provides for fantastic people-watching.
Divas
This colorful transexual nightclub/bar has three floors of bars, drag shows, and erotic dancing. It attracts a lot of transgender people and that is what the shows predominantly showcase, but everyone is welcome. It advertises itself as "the premiere transgender nightclub on the West Coast."
Element Lounge
Progressive, upscale Tendernob Hip-Hop and dance club with a modern earthy decor. It features live music and DJs, and executive table service if you can afford it.
Ruby Skye
Ruby Skye is one of the premiere clubs in the area and has become a "place to be seen." Some of the top DJs in the world have played here including Paul van Dyke, Pete Tong, and Sasha. It's 15,000 square feet of Hip-Hop, House, and Techno over multiple floors; one of the floors at the top has a private smoking lounge and cigar bar.
Mitchell Brothers O'Farrell Theater
Tourists have flocked here for live, nude girls and dirty movies since 1971, when porn star Marilyn Chambers followed her performance in a Mitchell Brothers' film by becoming an Ivory Snow model. The venue is large, clean, and the biggest rip-off in adult entertainment this side of Paris. If possible, avoid this over-priced, over-hyped tourist trap for the Crazy Horse on Market next to the Warfield or any of the clubs on Broadway in North Beach.
Suite one8one
Another large 16,000 sq feet, swanky nightclub in the heart of the gritty 'Loin. This modern club has resident DJs that spin hip-hop and house music. It definitely attracts a more upscale crowd and there is a strict dress code in effect... so if you've got sportswear on you probably won't get in!
Bars
Hanaro
Just across from the Edinburgh Castle is a shadowy hole-in-the-wall festooned with Korean lettering: Hanaro. Though the bar is wallpapered with "No Smoking" signs as California law demands, you need only loiter outside the bar for a few minutes with a cigarette before you are beckoned inside and offered an ashtray. In fact, Hanaro's great charm is it that it's accommodating in every respect; stay for a bit and you will be offered various bar snacks, and there is usually a hostess on hand whose only job is to chat with the patrons. This is done, however, with taste and tact; if you wish to drink in silence, you won't be disturbed. The jukebox is stocked with Asian pop singles.
21 Club
Old time dive bar that has been around since the time the neighborhood was full of sailors. They have a HUGE window that overlooks the Turk/Taylor intersection, and it probably delivers more entertainment than any TV you'll ever buy, showing all kinds of Tenderloin action going down; like prostitutes milling about, ambulances flying around, and Vietnam Vets just looking for a break. They serve cheap drinks and the patrons range from surly full time alcoholics, to friendlier neighborhood personalities... but hey, that's the 'Loin!
Bourbon and Branch
This hard to find cocktail/spirit themed bar is a throwback to the prohibition days of the 1920s — this address used to be an thriving illegal "speakeasy" known as the "JJ Russell's Cigar Shop." Inside it's ornately decorated with dark woods giving the place a real cozy feel. It being a prohibition themed bar, they also have some strange house rules posted on the walls like "no photography" and "Please speak easy" They have an exhaustive selection of spirits and cocktails.
The Brown Jug
Another classic dive-bar in the 'Loin. Again, a friendly atmosphere permeates throughout, and it's got its own set of die-hard locals who come down for a bit of fun and some cheap booze. It has an internet juke box and a small pool table to liven things up.
Deco Lounge
Deco lounge is a gay bar in the Tenderloin that has three floors. It's close to the Civic Center and a good place to go if you're in town to see the Pride celebrations.
Edinburgh Castle
Expatriates from the British Isles are often to be found at this Scottish pub, which on Thursdays through Saturdays becomes a hipster mecca. The interior is warm and shadowy, a comfortable place of dark wood and golden lantern light, and the beer selection is good; you can get pints of Belhaven or Newcastle as well as the ubiquitous Guinness, and it's all available by the pitcher. The Edinburgh Castle also has a relationship with a local fish and chips fryer, so you can order from their menu and have it delivered to you at the pub. The jukebox is well stocked with punk rock, Irish folk/rock, and American roots music, and live bands also play regularly which can unfortunately make it impossible to carry on a conversation. A trivia contest is held on Tuesday nights. And on Burns Night January 25th, the Edinburgh Castle is the place to be, with ribald poetry readings, music, and a public haggis.
The Gangway
This nautically-themed dive bar is home to a group of chatty regulars, mostly gay middle-aged men, who are friendly to newcomers of any age, gender, or sexual orientation. Many of them have lived in San Francisco for decades, and they have great stories.
Blur
Upscale, lush, candlelit bar in the Polk Gulch. It's dark and romantic and they have a good selection of cocktails... try the strawberry margarita. They also have free pizza on Monday nights.
Hemlock Tavern
Situated in the area known as the "Polk Gulch," this ever entertaining little rocker bar has a music room in the back where rock-and-roll bands play. It's nicely decorated wooden interior makes it feel cozy and inviting and they also have a heated smoking lounge.
The Nite Cap
If you are looking for an authentic Tenderloin dive bar experience with cheap drinks, questionable drinking partners, scarey looking bar snacks, in a "no-frills" environment — bingo, the Nite Cap is your thing!
The Owl Tree
A small, quiet upscale bar that's great for conversation and relaxation after a long day of wandering around San Francisco. What used to be a dive bar with walls adorned with tacky owl memorabilia, is now another upscale watering hole in the 'Loin, where cocktails have replaced draft beers as the drink of preference. There's still a mosaic owl on the outside though.
Vertigo Bar
Fun and trendy bar in the Polk Gulch. It's exotically decorated and attracts mostly partying twentysomethings looking to get enebriated on strange cocktails. They have DJs, dancin, a smoking patio, and are known for their lengthy happy hour which runs until 9PM.
Olive SF
Stylish cocktail bar in the Tenderloin. It has reasonably priced drinks and food pizza,tapas and the like in an informal yet trendy atmosphere. Not surprisingly they specialize in martinis, like the "Ultimate Olive Martini."
Coffee
farm:table
Very tiny spot with one large "farm table" thus the name and limited outdoor seating/standing bars. They serve coffee from nearby Santa Cruz roaster, Verve and have their own delicious sweets and other foods that they make daily. Very popular with the locals.
Jebena
Nicely decorated modern spot along the Polk corridor with good coffee and tea selections.
Soluna Cafe and Lounge
Just a stones throw from the performing arts buildings, it's a great place to grab a cappuccino just before the overture.
What a Grind
Decent, but basic spot for a cup of coffee where a lot of locals in the neighborhood go, especially while using the laundromat next door.
Hooker's Sweet Treats
Great spot to pick up handmade chocolate caramels, bread pudding, and coffee from local roaster, Sightglass. Very cute interior decorated in an antique style and owned by a Louisiana native.
Starbucks
Ubiquitous Starbucks set just behind the Civic Center Plaza, so another convenient place to enjoy a coffee pre or post performance.
These days the Tenderloin is on the "up-and-up," and with this urban gentrification has come a surprisingly eclectic and artistic nightlife scene. It now has a decent selection of trendy lounges and hip clubs, as well the musical venues many of which are listed under Performing arts above, strip-clubs, and "dive bars" that were the more traditional staples of the area. In fact, many of the modern "faux-dive" and "dive bars" used to be illegal speakeasies during the prohibition era of the 1920s. Given the areas long and storied association with the Gay, Lesbian, Bisexual, and Transgender community the "Polk Gulch" was the city's first openly Gay neighborhood, before the emergence of the Castro in the 1970s, many of the bars, clubs, and entertainment are geared toward this crowd, although typically everyone is welcome.