SINGAPORE – A significant chapter in Singapore’s entertainment history came to a close with the shuttering of nightlife outlets at Orchard Towers in late 2023.

Its vice-tainted location at 400 Orchard Road is a shadow of the sophisticated cabaret performances that played there and made headlines in the 1960s.

But Orchard Road was always destined to be a great street for all sorts of commerce.

In 1968, it grabbed headlines around the world when Singapore’s first entertainment complex called the Tropicana Theatre Restaurant and Niteclub opened in Scotts Road.

It was Orchard Road’s first major attraction, which later paved the way for the thoroughfare’s journey in transforming itself into one of the world’s foremost retail and fashion draws, on a par with Fifth Avenue in New York and the Champs-Elysees in Paris.

The nightspot was the culmination of a series of talks in the 1960s between the Singapore Tourist Promotion Board (STPB), now called Singapore Tourism Board (STB), and the local business community. They were aimed at adding buzz to the street, which in the 1960s was popular as a grocery-shopping haunt, with colonial-era supermarkets such as Fitzpatrick’s and Cold Storage.

There was also a cinema hall called Pavilion, mainly for the British to catch up on Hollywood hit films and drink whisky at the same time.

STPB collaborated with property developer Shaw Sung Ching to come up with early sketches for Tropicana in 1966, which turned out to be a game changer.

The classy Tropicana, with its fine dining and topless European troupes, was a shot in the arm for then-sleepy Orchard Road. International royalty, celebrities and jet-setters downed a mouthful at its sophisticated fine-dining restaurants, then were later in for an eyeful at the nightclub’s nightly shows.

When it was officially opened by then-STPB chairman P.H. Meadows, on March 30, 1968, on a 25,000 sq ft plot, Mr Shaw declared that for the first time, the Republic was on an equal footing with world-class nightclubs with cabaret shows in Asia, such as the Mikado in Tokyo.

“We believe that such a complex will not only meet the needs of the most demanding nightclub-goer, but also become another reason for the international traveller to want to come to Singapore,” said the late Mr Shaw, a Shanghai-trained architect who made his fortune in the construction sector after arriving in Singapore. He died in 2003 at the age of 93.

Tropicana was such a success that it was fully booked every night for its first three years. It closed in 1989 after stiff competition from topless revues at Neptune Theatre Restaurant in Collyer Quay and Golden Million at Peninsula Hotel.

Tropicana’s allure also began to fade after a new music phenomenon called disco swept the world with its throbbing music and catchy lyrics. This new entertainment wave coincided with Singapore’s hotel construction boom of the late 1960s and 1970s.

Hoteliers wasted no time opening discos to capitalise on the rampant demand for cramped spaces with strobe lights, mirror balls and the blaring disco music of Donna Summer, the Bee Gees and the Village People.

From the 1960s to the late 1980s, discos started popping up all over Orchard Road, such as Barbarella at Ming Court Hotel (1970), Xanadu In Shangri-La Hotel (1981) and, later, Top Ten at Orchard Towers (1985).

Building a great street

Between 1999 and 2001, Singapore-based global architectural practice DP Architects (DPA) served as the lead consultant on a schematic planning study commissioned by STB in dialogue with various local agencies, Orchard Road Business Association (Orba) and other stakeholders. The brief: to transform Orchard Road into a globally recognised destination.

Mr Jeremy Tan, 61, a DPA director who was involved in the earliest Orchard Road masterplan then, recalls some of the big ideas that were discussed.

“There was talk about linking the different buildings and districts in Orchard Road and raising the concept for an underground pedestrian network connecting major crossroads,” says Mr Tan, who has been with the firm for more than 30 years.

“We also looked at how to seamlessly integrate malls with the streetscape to draw the crowds out and extend the Orchard Road experience, raising the idea to open up the malls from their traditionally closed facade designs.”

Mr Tan says the team studied internationally renowned retail concepts and experiences in global cities. The benchmark: to see how they could reimagine Orchard Road as a “great street” with the vibrancy and dynamism of the world’s best shopping streets.

He notes that these efforts are evident today in the seamless connectivity that makes Orchard Road pedestrian-friendly and in the green respites along its streetscape with its many cafes, the food and beverage (F&B) kiosks and street performers. “And in the changing faces of the malls with their inviting facades that blend seamlessly with the streetscape to extend the Orchard Road experience beyond four walls,” he adds.

“The exciting part is also the new works and programming that are ongoing and new plans that are envisioned for Orchard Road that will continue to make this one of the most iconic streets of Singapore.”

Since the 1980s, DPA has been involved in the design and reinvigoration of about 10.76 million sq ft of mixed-used commercial spaces and has also helped reinvent 20 buildings in Orchard Road, such as Wisma Atria, Orchard Central, Paragon Shopping Centre and Mandarin Gallery.

Mr Chua Zi Jun, 45, DPA director and design lead for retail typology, cites Wisma Atria as an example of how one building tells the story of Orchard Road’s evolution and progress – from when it was first built in 1986 by pioneer architect Gan Eng Oon, then revamped twice by DPA chairwoman and veteran architect Angelene Chan.

Wisma Atria, Mr Chua notes, was first built in a 1980s American mall typology featuring an atrium in a centred box form, reminiscent of contemporary designs then.

In 1991, the Urban Redevelopment Authority (URA) released a revised concept plan to modernise Orchard Road and Wisma Atria was given a facelift in 2004. Its facade was reconstructed with a glass frontage that changed the building’s elevation into a storefront window with external escalators going to the upper floors, connecting its multi-storey retail shops with the sidewalk.

“This revamp made Wisma Atria the first in the region to reverse its ‘closed’ design into an open one,” recalls Mr Chua, who notes that many malls subsequently followed suit and modernised.

This gave rise to the street-integrated urban mall, which refreshed the face of Orchard Road, increasing its vibrancy with pedestrian and side-street activities.

Wisma Atria underwent another makeover in 2012, when Ms Chan designed a glass facade to further increase its visibility and street engagement.

“These efforts to transform Orchard Road’s buildings and foster connectivity has helped shape its evolution over the decades,” says Mr Chua.

He adds Orchard Road’s rejuvenation and transformation continues today, with one of the largest redevelopments comprising Forum The Shopping Mall, voco Orchard Singapore and HPL House, to form a mixed-use development.

“This redevelopment is set to further revitalise the area and, when built, will feature the first performance theatre and one of the largest rooftop gardens in Orchard Road.”

In 2019, STB, together with URA and National Parks Board (NParks), announced plans to strengthen Orchard Road’s position as a lifestyle destination and to bring back the orchard in Orchard Road.

As a lifestyle destination, it will have sub-precincts with unique identities. For instance, Somerset will have a “youth vibe”, while the carpark in Grange Road near Somerset MRT station will be reimagined as an event space combined with retail offerings.

The shopping belt will also become a lush green urban corridor connecting to historical green spaces, such as Singapore Botanic Gardens and Fort Canning Park. The streets will be enhanced through a curated showcase of vibrant trees and shrubs that depict the colours of the tropics.

Global draw for tourists

Today, Orchard Road is one of the world’s foremost retail and fashion shopping streets. According to the Singapore Tourism Analytics Network, Singapore received more than 12 million visitors from January to November 2023. Orchard Road remains a top draw for tourists here, garnering four out of five stars in 2024 on global travel site Tripadvisor, which rates it one of the must-see local places.

Ms Guo Teyi, STB’s director of retail and dining, says Orchard Road distinguishes itself through its dynamic fusion of shopping, dining and entertainment, catering to diverse consumer preferences. Ongoing rejuvenation efforts, driven by new developments and concepts from both public and private sectors, aim to enhance Orchard Road’s position as a must-visit lifestyle destination.

“The introduction of first-to-market concepts such as Trifecta, Asia’s first snow, surf and skating lifestyle destination; as well as flagship stores such as the Nike one at 268 Orchard; the addition of hospitality and dining offerings, such as the newly opened five-star hotels The Singapore Edition and Artyzen Singapore; and French patissier Cedric Grolet’s first Asia outpost at Como Orchard; all contribute to the appeal,” she adds.

Mr Mark Shaw, chairman of Orba, notes that in the last 25 years, the nation’s economic growth, technological advances and shifting cultural trends have all transformed the retail landscape.

Orchard Road establishments have kept pace with these changes to remain relevant.

“Developers have been steadily reconfiguring older malls and designing new malls to accommodate more F&B outlets as Singapore evolves to become one of the major culinary hubs in the region, drawing not just Michelin-starred chefs, but also young local entrepreneurs who, within a few years, have created an exciting restaurant and cafe culture,” says Mr Shaw, 54.

Retailers have also pivoted with offerings to cater to changing consumer behaviour. Experiential shopping with artificial intelligence-assisted interactive features, omnichannel touchpoints and sustainable products are commonplace in physical stores and online today, he adds.

He has seen tourism demographics shifting significantly towards arrivals from China, Indonesia and India.

“Orba’s retail members are adopting a more differentiated approach,” says Mr Shaw. “Surveys have found that Chinese visitors spend more on shopping and less on accommodation and food. Practical measures include incorporating payment options, such as WeChat Pay and Alipay, that Chinese consumers can use.”

Orchard Road also boasts the biggest collection of international hotels along a 3.1km stretch. In addition, there is a presidential palace, an outdoor park for youth activities and a charming enclave of Peranakan shophouses – Singapore’s finest examples of Chinese Baroque-style shop-and-terrace houses – at Emerald Hill, says Mr Shaw.

“The diversity found in Orchard Road makes it unique, with a character that subtly changes as you delve into its many malls.”

Partying in new ways

Besides retail, lifestyle hot spots and an urban corridor, Orchard Road will offer something new by 2025 at the end of the stretch bordering Penang Road, where Temasek Shophouse now stands.

Temasek Shophouse is expanding to better cater to a growing community of changemakers and social entrepreneurs who are given access to event venues, co-working and community spaces, as well as networking opportunities to enhance and strengthen the impact work they do.

Besides the four shophouses involved in the expansion – No. 16, 22, 38 and 28 (the current Temasek Shophouse) – there are also plans to rejuvenate and activate surrounding outdoor spaces, including Handy Green and Stamford Canal, for the public to enjoy.

“With the transformation and expansion, Temasek Shophouse will be able to support more impact organisations, such as social enterprises, ground-up initiatives, social service agencies, non-profit organisations and charities with access to resources and networking within Temasek Shophouse’s community,” says Ms Yvonne Tay, general manager of Temasek Shophouse.

One person who is misty-eyed to see the last of the red-hot Orchard Road nightlife hot spots fade into the pages of history is entertainer-emcee Moe Alkaff. The 61-year-old was a resident deejay at Top Ten during its heyday in the 1980s before it closed at Orchard Towers in 2005.

“Top Ten was a legendary club where Singapore’s high society went to let their hair down,” recalls Mr Alkaff, who was in charge of the band line-up and deejayed there every night from 1985 to 1989.

“Models, ‘mad men’ from the advertising agencies and international airline crew had to get in line in snaking queues just to get in. Every night was like a Saturday night because the party never seemed to end,” recalls the entrepreneur, who founded events management company Moezik Events International.

But he says it is sad to see the nightlife element dialled down to just a few nondescript bars and pubs.

“Vibrant nightlife makes a place seem like the fun never ends and that is what is missing in Orchard Road. We need to find ways to bring the party back to our Great Street,” he adds.

“Orchard Road was the street to go to for serious partying. Now, people will be drawn to other places, such as Clarke Quay and Marina Bay Sands.”