It’s fascinating how the history of cocktails has been deeply embedded (much like other food traditions) within the fabric of society and its interplay of gender dynamics. With each generation, the narrative has changed, sometimes evolved and often regressed beyond recognition, but has been in a constant state of flux. 

Rail and road communication systems between Malaya and Singapore underwent significant upscaling in the 1990s. Such enhanced infrastructure bolstered traffic into Singapore on the weekends, mostly of palm oil and rubber plantation owners. 

Nestled in Cad's Alley, Long Bar was famously dubbed the 'Rendezvous of Planters' during its heyday. Operating more as an informal gathering spot than a conventional bar, it featured tables arranged along Bras Basah Road, providing a strategic viewpoint for male patrons to observe the passing parade of ladies.

Drawing inspiration from Malayan life in the 1920s, the two-story Long Bar boasts an earthy decor with deep, vibrant colours and abundant greenery, evoking the ambience of a tropical plantation. Embracing a laid-back vibe, visitors are encouraged (till date) to casually discard peanut shells onto the table and bar counter, creating a unique atmosphere where littering is not just tolerated but actively promoted.

Crafted in 1915 by Raffles bartender Ngiam Tong Boon, the Singapore Sling holds the esteemed status of the national drink in the island country. Comprising gin as its primary base, this iconic cocktail harmoniously blends lime juice, curaçao, pineapple juice, and Bénédictine. Infused with a charming pink hue, thanks to the addition of grenadine and cherry liqueur, Ngiam intentionally selected this rosy blush for the cocktail.

At the onset of the 20th century in colonial Singapore, Raffles served as the hub for the community, with Long Bar as its favoured parlour. Gentlemanly patrons were often spotted savouring glasses of gin or whisky. However, societal norms restricted ladies from public alcohol consumption, leading them to opt for teas and fruit juices to maintain a sense of the age ‘ol Victorian modesty.

A smart cookie, Ngiam decided to capitalise on this unfortunate disparity. He then decided to create a drink that would have an outer appearance of innocuous fruity splendour, all the while hiding potent (and most importantly, colourless) spirits within. And that was believed to be the origin story of the Singapore Sling. 

In another fascinating version of the drink’s origin, the tale unfolds with an army officer entering the bar and becoming captivated by the enchanting Lady Chin. As the youngest daughter of a prosperous silk merchant, her resplendent beauty and ruby lips held the man spellbound.

“With painted lips of crimson red that curled up in the slightest hint of a smile, and eyes that glittered with bemusement as she looked about her, the young woman sat by herself at the furthermost corner of the room as if content enough amidst the boisterous chatter that surrounded her. She was the most beautiful woman he had ever seen in his entire life.”

Hardly able to contain his awe, the officer walked up to Ngiam and asked the latter to whip up something for her. When Ngiam asked if the officer would like to send over the patent scotch, he reacted with shock. “Goodness no, old chap. A scotch is simply not the right drink for a woman of her bearing!”

Thus he asked the bartender to make “A cocktail. Something alluring. Something red. Something which will match her totally!” Thus, the Singapore Sling. 

In no time, the drink gained popularity and acquired the moniker "Commander's Drink" (maybe a hat tip to the officer's infatuation). The Hainanese term for "Commander," pronounced as "si ling," led to the name "Sling." It is believed the officer's enchanting encounter with Lady Chin culminated in a joyous wedding, adding a happy ending to the tale.