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The Roaring ’20s are back at this new drinking den in Downtown SF

The Harlequin will specialize in eye-catching craft cocktails. | Courtesy Phil Chen

In the 1920s, Downtown San Francisco shimmered with opulent palace hotels and restaurants that were constructed after the 1906 earthquake. Darkened windows concealed speakeasies where residents hid illicit liquid in their glasses. A century later, Phil Chen plans to open a new cocktail lounge and kitchen called The Harlequin in mid-June that will honor the building’s Prohibition-era origins.

The black marble facade of the corner space at Fourth and Jessie streets dates back to 1913, when it was installed for the Keystone Hotel. Chen said he learned from building owner Charles Mosser that the hotel hosted lavish parties in the 1920s—a tradition Chen said he hopes to carry on at his new bar. 

“We’re reimagining what the place would have been like back in its glory days,” he said.

Most recently, the building was home to the Keystone Social House, a tavern that took its name from the original hotel and which shuttered in 2020 during the first Covid shutdown. Before that, it had been a bar and bistro called Annabelle’s—named after Mosser’s wife.

According to Chen, the new name nods to the building’s living history. When he first walked into the space, he noticed floor tiles patterned after a court jester's costume. Chen said the tiles captured his imagination and inspired an intention for the bar. The Harlequin was born.

“I want the place to be fun—and for people to know that we don’t take ourselves too seriously,” he said. 

Chen told The Standard that we can expect a similar menu of colorful craft cocktails and shareable plates from his other businesses, steampunk bar Alchemist and gastropub Woodbury—both in South Beach—as well as his third bar, Members Only in Lower Nob Hill. Though The Harlequin’s menu is still in development, he said he plans to serve steak, pastas, pizzas and flatbreads. After the soft opening, Chen said he’ll add a lunch menu.

Chen, who immigrated to the U.S. from Shanghai at the age of 6 and moved to San Francisco in 1989, worked in tech before pivoting to hospitality. He used to frequent Annabelle’s after work, and that one day while scouring Craigslist, he noticed the space was up for rent. It was never his long-term plan to open a fourth bar so soon after launching Members Only. 

“My wife says I’m not allowed to browse Craigslist when I’m bored anymore,” he said, laughing.

Located across from the Marriott Marquis and half a block from the Moscone Center, Chen said he expects to cater to conventiongoers but also hopes that The Harlequin will become a neighborhood hangout for folks who live and work nearby. 

“I want this to be a place where people from here will be taken care of,” he said.

The Harlequin