Categories: Broke-Ass City

Speakeasy and carry a stiff drink

We approached a woman in an orange hat standing near the corner of Broadway and Columbus Avenue and asked, “Do you know where to get a good slice of pie?” Her answer was something innocuous, maybe about the weather, but signified that, indeed, she was our contact. We were in the right place.

The lady pointed us in the direction of our next contact. Speaking in the kind of mid-Atlantic accent you only hear in old movies, our second contact double-checked our identities and sent us toward the entrance of an old Chinese laundry. Descending the stairs inside, we weren’t simply entering a basement — we were actually going back in time and, when we hit the landing, we were in 1923.

This was The Speakeasy, San Francisco’s wonderfully immersive theatre experience and the only way in town to properly time travel.

Taking place on a single evening during Prohibition, The Speakeasy follows 35 characters, and just as many storylines, as they navigate the ups and downs of love and loss in the time of jazz and illicit booze. When we got our tickets online, we were instructed to dress in time period-appropriate attire. (Not making any attempt to dress up ruins everyone else’s ability to suspend disbelief, which is the entire point of the show.) Once we entered and were seated at a table in the barroom, it was hard to tell the difference between the cast and audience. And that’s where the magic really lies …

Immersive theatre is just what it sounds like: There is no stage and there are no rows of seats. The show happens all around you, and the experience is based on choices. You can follow one particular character throughout the evening or hop around checking out what different ones are up to. We started the evening in the barroom; others begin in the casino and in a room with a vaudeville-esque stage show.

While drinking strong Prohibition-era cocktails at our little table, a loud drunk at the bar started heckling other patrons while a two-man comedy troupe performed a back-and-forth punch line routine. Suddenly, a couple guys burst through the door talking a little too loudly about their bathtub gin operation, and we were able to divine who was an actor. After 30 minutes or so, we were invited to wander the grounds and explore.

We ambled into the casino and, after playing some craps, were told of another hidden bar with more tables to play at. But on our way, we got sidelined by the chorus girls shimmying and singing onstage. We met Sal, the joint’s proprietor, and listened to him lament the headaches of running a speakeasy, and then got caught up in the longing of the waitress who desperately wanted to be onstage.

We met fiery feminists, lapsed teetotalers, degenerate gamblers and sassy chanteuses. But we could’ve just as easily spent the entire evening chatting up the sharp-tongued bartender as he poured stiff drinks. There were multiple times throughout the night when someone we thought was a patron suddenly became the center of attention and pulled an audience member into their story. One of the best parts of this immersive theatre experience is getting roped into one of the character’s shenanigans because it keeps the rest of the crowd wondering if you were actually a cast member all along. On this trip, I was pulled onstage to help with a magic trick; on a previous visit, Sal took me into his office and gave me a delicious cannoli because he said I looked like a guy who could appreciate one. (Spoiler: I am!)

Part of the wonder of The Speakeasy is that it’s a different experience every time you visit. I’ve been three times, and have been completely caught up in it each time. With the right amount of booze and the perfect companions, The Speakeasy has the ability to make you almost believe you really are in 1923.

Wanna visit The Speakeasy? Check it out at

Stuart Schuffman, aka Broke-Ass Stuart, is a travel writer, TV host and poet. Follow him at Broke-Ass City runs Thursdays in the San Francisco Examiner.

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