The 50-room Hotel Cairns at 36th and Fulton opened in 1907 as a high-class hotel on the (then) far outskirts of town. Originally constructed in 1896, the building was redesigned by Armitage & Rowell, and was heralded in newspapers as one of the classiest joints in the country. The popularity of automobiles soon made the hotel far more accessible than Cairns imagined, and it quickly turned into a rowdy roadhouse.

Originally opened in the middle of Golden Gate Park near the Conservatory of Flowers in 1882, the Casino Roadhouse instantly got a bad reputation for spoiling the virtues of the park by inciting people to drink. Though successful, it closed for a few years and served as a small museum and park offices. By 1896, the building was relocated to Fulton between 24th and 25th avenues as a roadhouse—outside the boundaries of the park in an area uninhabited enough that the patrons could be as loud as they wanted.

The Barbary Coast has a raucous history, full of saloons, brothels, and shanghaiing. When the Barbary Coast was essentially shut down in 1917, the Hippodrome remained, along with its plaster casts of, uh, very friendly nymphs and satyrs.

John J. Ford and Emil Holje opened a saloon in what is today the Bayview, catering to the workers who lived in the area—immigrants working at shipyards, tanneries, bakeries, butchers, and more.

Gold Rush San Francisco was a dirty, dusty town, and no place personified that better than Warner's Cobweb Saloon. Literally covered with curtains of cobwebs hanging from the rafters, the saloon, run by eccentric Abe Warner, was filled with oddities from around the world, along with a menagerie of animals that ran free around the bar.

Duffy's Bar was formerly located at the corner of Beach and Baker streets. It was torn down around 1915 to make way for the Panama Pacific International Exposition. In its place went a little something called the Palace of Fine Arts.

The Road to Mandalay was a West Portal cocktail lounge that operated from 1940 to 1961. Designed to feel like a luxury liner salon, this is definitely 1940s kitsch at its peak. Inside, the nautical theme continued, with ship wares decorating the place. The exterior featured iron rails and ladders, portholes through double doors, and even a uniformed steward to open the door for you. It stayed in business until 1961.

For almost 150 years, the Cliff House has sat upon the precarious cliff overlooking the Pacific Ocean. Originally built in 1863, it eventually became a favorite spot for frequenters of the Barbary Coast, and became infamous for "scandalous behavior." Adolph Sutro bought it in 1881 with hopes of turning it back into a family place, but the original building burned down in 1894.

Founded in 1867 by George Mayes, the restaurant had a very different past, including a separate entrance to the bar before ladies were allowed, a speakeasy downstairs, and rooms upstairs for, uh, working girls. Mayes' son transformed it into an Italian seafood joint, and since then a few other eateries have been housed in the space.