“I think this would be a good time for a beer.”
Those were the famous words of Franklin D. Roosevelt when he repealed Prohibition with the 21st Amendment. While he may have ended that era, it also gave us some of our favourite classics. Drinks created between the 1920s and 1933 remain a cornerstone of cocktail culture, and it was an era I was happy to be transported to over the long weekend by the team at the St. Regis Bar during its once-a-month Jack’s Club experience.
How did the Prohibition era come about?
The 18th Amendment banned the manufacture, sale, and transportation of alcohol nationwide from January 1920. Rather than stopping people from drinking, it drove it underground: speakeasies, secret bars hidden behind unmarked doors, password entry, bartenders in suspenders, jazz music, and cocktails designed to mask the taste of poorly made bootleg spirits. At its peak, there were an estimated 30,000 illegal speakeasies in New York City alone. The cocktail culture that came out of this period is still the backbone of every serious bar menu today, including Jack’s Club’s entire menu.
After attending a week-long conference where every panel spoke about AI, it was refreshing to see that the fine art of jazz and speakeasy bars is still firmly human-led. It’s what makes us human and connects us to history.
This bar is easy to walk past, quietly hidden behind a red curtain just past the hotel entrance on Tanglin Road. Behind it, the newly renovated St. Regis Bar is doing something few rooms in Singapore attempt: a full, unironic commitment to an era. The bartenders and staff add to the drama with their Prohibition-era dress. There is a reason the Prohibition-era bar never goes out of style: the low light, the live music, the atmosphere. This is not an everyday affair. It journeys back to the Prohibition era only on the last Friday of each month. For the rest of the week, it is the St. Regis Bar, but on that one Friday it becomes the secret Jack’s Club. The room feels different when people know it will not be there the following week. The scarcity adds to the theatricality.
The room is deep red and candlelit, with eight Picasso prints on dark-panelled walls. We were shown to our table, handed two menus at once, and immediately got excited by the options. We wanted to order everything, but between the two of us we decided to start small, test our appetites, and see how much to indulge. The menu seemed worthy of gluttony, and we ended up trying three of the small plates and four drinks.
The food arrived and vanished within minutes; either we were very hungry or it was genuinely delicious. I’m leaning towards the latter, as tables around us seemed to have the same reaction. The potato churros were finished before anyone suggested sharing: crisp, hot, with a dipping sauce that justified the speed. The Sandfish Bay oysters with caviar turned out to be the most-ordered dish in the room that night. You could tell by how many plates moved through neighbouring tables in quick succession. The Petit Burger arrived next: wagyu, avocado, aged cheddar, caramelised onion. Small enough to feel like a bar bite, yet good enough to make you wish you had ordered two. The Reuben followed on rye with corned beef, sauerkraut, and Swiss cheese, and made a completely convincing case for itself in a room this glamorous. The Chilli Crab Mantou closed out the food order with the confidence of a dish that knows exactly what it is: crispy bun, crab mayo, and chilli heat that builds slowly. Singapore in three bites, dressed up for a Friday night.
The cocktails run to six signatures, all between $28 and $30. The Princess Cut came first, ordered on the strength of Ruinart in the ingredients list. Founded in 1729, Ruinart is the oldest established Champagne house in the world. It brings a particular delicacy to everything it touches: lighter and more mineral than most, less about power and more about precision. In the Princess Cut, it works alongside Planteray Rum, egg white, grenadine, and lemon to produce something frothy and elegant in a coupe, pale as a blush. We ordered it again before the first was finished. The Cloak and Dagger came next: Michter’s Kentucky Straight Rye, D.O.M. Bénédictine, Carpano Antica Formula Vermouth, and Peychaud’s Bitters. It sits in the Old-Fashioned family but has its own distinct character: drier, more aromatic, the kind of drink that makes you lean back rather than forward. The Merlion Sling—Roku Gin with pineapple tepache, Cherry Heering, Bénédictine, and Fever-Tree Ginger Beer—is the menu’s love letter to Singapore, written in botanical ink. The 21 Club Southside, gin with lemon and mint, served as the clean, cold reset between rounds.
At 8pm, the jazz started. The stage backdrop had been waiting for this moment and earned it. This is a good place to come with friends. Claim one of the deep booth seats along the back wall, order a round, and let the music arrange the rest of the evening for you. Conversation drops half a register without anyone deciding to let it. At some point during the set, my friend leaned over to request a song from the singer. Before she could catch anyone’s attention, the band moved straight into it—the exact song. We looked at each other and said nothing, which was the correct response.
The launch had not been widely publicised. That intimacy was part of what made the night feel like a discovery rather than an event to attend. The crowd was a genuine mix: hotel guests, Singapore residents who had caught wind of it, and a few tables who appeared to have wandered in entirely by luck. At 11pm, a DJ took over and the Prohibition-era party continued.
One last thing worth noting: Jack’s Club sits on Orchard Road, and Orchard Road is not what it once was. For years, the neighbourhood meant shopping centres and hotel lobbies, and not much else for anyone who came to eat and drink seriously. That is changing. Between the St. Regis, the Singapore Edition, 67 Pall Mall’s new public opening at Shaw Centre just up the road, and a growing number of serious F&B concepts reclaiming the area, Orchard is becoming a destination again—not a corridor between malls, but a neighbourhood with its own identity after dark. Jack’s Club is part of that story.
It happens on the last Friday of every month. Block your calendar for the next one.
Cocktails $28–$30 | Bar bites $18–$26 | Smart casual
