Transgender people in Singapore
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The history and subculture surrounding transgender people in Singapore is substantial. Not immediately apparent to Singapore's mainstream society is the fact that the gay community sees itself as a totally separate entity from the transgender communities (often also referred to as "transvestite and transsexual" communities). They are individual subcultures with many different priorities and concerns.
National service was implemented in 1967, whereby all 18-year-old males were required to train full-time for two or two-and-a-half years, depending on their educational attainment. Transgender was listed as a condition in a Singapore Armed Forces (SAF) 'Directory of Diseases' and recruits who outed themselves to the examining doctors at the Central Manpower Base (CMPB) at Depot Road had their 'deployability' denied in sensitive positions. They were classified as Category 302 personnel, downgraded to a Physical Employment Status of C or E and assigned only non-combat roles at military bases.
"Transgender individuals who have undergone sex reassignment surgery (SRS) are able to skip National Service entirely. However due to the difficulty of transitioning early, only a very small percentage of transsexuals in Singapore are actually able to obtain SRS before having to enter National Service. In rare cases, it's possible for transgender people to be exempted from National Service despite not undergoing sex reassignment surgery. However this is mostly up to the medical-officer in charge and varies case by case. In general, transsexuals that look like cisgender females have a much higher chance of being exempted." 
Early sex reassignment surgery
As Singaporean gynaecological surgeons became more skilful, leaders in the field like Prof. S Shan Ratnam were authorised to perform Sex reassignment surgery male-to-female (SRS) at Kandang Kerbau Hospital. The first such operation in Asia took place in Singapore in July 1971. However, before patients could go under the knife, they first had to subject themselves to an exhaustive battery of tests and be given a clean psychological bill of health by chief academic psychiatrist Prof. Tsoi Wing Foo.
"In 1973, Singapore legalised sex-reassignment surgery. A policy was instituted to enable post-operative transsexual people to change the legal gender on their identity cards (but not their birth certificates) and other documents which flowed from that. There was no specific provision in the statutes which allowed the Registrar to do this, so it existed probably only at the level of a policy directive. However, for over 20 years, this policy seemed to have operated smoothly."
Further developments in sex reassignment institutions
Later, the more technically demanding sex reassignment surgery female-to-male was also offered at Kandang Kerbau Hospital and at Alexandra Hospital, performed by gynaecologists such as Dr. Ilancheran. A Gender Identity Clinic (GIC) and Gender Reassignment Surgery Clinic were set up at the National University Hospital two decades later. It was headed by Prof. S Shan Ratnam until his retirement in 1995, after which leadership passed to his nephew, Dr. Anandakumar. In fact, for 30 years, Singapore was one of the world leaders in SRS, performing more than 500 such operations. This gave a new lease on life to the many transgender individuals whose bodies did not match their gender identity. As one consequence of this, Bugis Street and Johore Road started to become populated with a range of transgender people from transvestites to iatrogenic intersex individuals to fully transformed women.
Legalisation of transgender marriage
Since the mid-1970s, post-operative transsexual people had been discreetly lobbying to be given the right to marry opposite-sex spouses. In 1996, a bill was presented before the Parliament of Singapore and the Women's Charter amended to read:
- Avoidance of marriages between persons of same sex.
- (1) A marriage solemnised in Singapore or elsewhere between persons who, at the time of the marriage, are not respectively male and female shall be void.
- (2) It is hereby declared that, subject to sections 5, 9, 10, 11 and 22, a marriage solemnised in Singapore or elsewhere between a person who has undergone a sex reassignment procedure and any person of the opposite sex is and shall be deemed always to have been a valid marriage.
- (3) For the purpose of this section
- (a) the sex of any party to a marriage as stated at the time of the marriage in his or her identity card issued under the National Registration Act (Cap. 201) shall be prima facie evidence of the sex of the party; and
- (b) a person who has undergone a sex reassignment procedure shall be identified as being of the sex to which the person has been reassigned.
- (4) Nothing in subsection (2) shall validate any such marriage which had been declared by the High Court before 1 May 1997 to be null and void on the ground that the parties were of the same sex.
The minister moving the bill argued that since 1973, the government's intention was for people who had changed gender/sex to live a life according to their new gender, including the right to marry. Through an oversight, the law relating to marriage had not been re-aligned with the official policy to recognise sex reassignment surgery. Now that the courts had illuminated this inconsistency after a landmark case in which a woman sought and won the annulment of her marriage to a trans man (Lim Ying v Hiok Kian Ming Eric), it was necessary to amend the Women's Charter to ensure that the original intent was not undermined. Transgender people were officially granted their wish on 24 January 1996 via an announcement by MP Abdullah Tarmugi without much public fanfare or opposition.
Closure and reopening of the GIC
The Gender Identity Clinic (GIC) at the National University Hospital quietly closed in 2001. The official explanation was that the gynaecologist in charge had left for private practice, and without him, the clinic did not have the skills to perform SRS. However, as early as 1987, the Ministry of Health had been directing hospitals to stop doing such operations on foreigners. It also discouraged them for Singaporeans, saying 'the increased danger of AIDS with such patients poses unnecessary risk to hospital staff'.
This dismayed transgender people seeking to have their operations performed locally. The online edition of the now-defunct newspaper Project Eyeball carried out a survey in June 2001 asking, "Should sex-change operations be resumed in Singapore?" 39% of respondents said, "Yes, they are people with valid medical needs, like infertile couples" and 35% said, "Why not? It is legal here, as are transsexual marriages". The results showed that Singaporeans were generally quite supportive.
The transgender community petitioned for the GIC to be reopened and were successful, with the clinic discreetly resuming its services in 2003, helmed by Dr. Ilancheran. However, owing to the discrimination against transgender people in Singapore even within some segments of the medical community, the high financial outlay involved and the necessity for psychological clearance, many preferred to have their operations performed sans the hassles in Bangkok, which had by then become the première centre for SRS.
One of Singapore's most famous tourist meccas since the 1950s, renowned internationally for its nightly parade of flamboyantly dressed trans women, Bugis Street attracted hordes of Caucasian gawkers who had never witnessed Asian queens in full regalia.
The latter would tease, cajole and sit on visitors' laps or pose for photographs for a fee. The amount of revenue that they raked in was considerable, providing a shot in the arm for the tourism industry. Veterans recall that the notorious drinking section began at Victoria Street, and proceeded west to Queen Street. Halfway between Victoria and Queen Streets, there was an intersecting lane parallel to the main roads, also lined with al fresco bars. There was a well-patronised public toilet with a flat roof of which there are archival photos, complete with jubilant rooftop trans women. The earliest published description of Bugis Street found by Yawning Bread as a place of great gender diversity was in the book "Eastern Windows" by Ommaney, F.D. (1960. London:Longmans. pp. 39–45). Ommaney did not date specifically his description of the street, but his book made clear that he was in Singapore from 1955 to 1960.
In the mid-1980s, Bugis Street underwent major urban redevelopment into a retail complex of modern shopping malls, restaurants and nightspots mixed with regulated back-alley roadside vendors. Underground digging to construct the Bugis MRT station prior to that also caused the upheaval and termination of the nightly transgender sex bazaar culture, marking the end of a colourful and unique era in Singapore's history. Tourist and local lamentation of the loss sparked attempts by the Singapore Tourist Promotion Board (STPB) to attempt to recreate some of the old sleazy splendour by staging contrived "Ah Qua shows" on wooden platforms, but these artificial performances failed to pull in the crowds. They were abandoned after a short time.
Bugis Street was immortalised in an English-language film of the same name, made, ironically, by a Hong Kong film company which did employ some local talent in its production.
Formerly located between and parallel to Queen Street and Victoria Street, and bisected by Ophir Road, Johore Road was the less well-known cousin of its glamorous counterpart, Bugis Street, just a stone's throw away. It was the seedy haunt of transgender sex workers who solicited sex from locals, away from the glare of Western tourists. No photographs or media attention were focused on this street of ill-repute; only a no-frills approach to an economic exchange.
It was one of the few roads to be completely erased from the map of Singapore after a fire in the late 90s, to be replaced by an unnamed park next to the Bugis MRT station and the Victoria Street Wholesale Centre.
Boom Boom Room
Boom Boom Room was Singapore's only drag queen cabaret nightclub and thought by many also to be Singapore's only real national institution in the same uninhibited spirit as the original Bugis Street. It is the namesake of John Lee Hooker's legendary blues club in San Francisco, shooting to international fame when the postmodernist magazine Wallpaper called it "our top pick for a good night out in all of Asia!"
Originally established by owner Alan Koh in 1993 at 4 New Bugis Street in Bugis Village, it later relocated on 2 April 2000 to the second floor of the old 2-storey Chui Eng Free School schoolhouse at 130–132 Amoy Street, Far East Square (10 min walk from the Raffles Place MRT station). The new venue, which was reputed to have the best Singapore Sling in town, had a restaurant downstairs for informal and outdoor dining.
Its overwhelming attraction were the risqué comedy routines by local drag superstar Kumar who took no-holds-barred digs at topics close to the hearts of Singaporeans. He was aided by his coterie of flamboyant, dazzlingly costumed, cross-dressing backups, nubile toyboys and other straight stand-up comedian friends.
The first performance debuted on 18 August 2000. There were 2 shows each night and outrageous wisecracks, in raw Singlish which made the banter difficult for tourists to understand, were interspersed with DJs playing the latest chart tunes. Members of the audience sitting next to the stage ran the highest risk of being drawn into the performance. It was patronised by a largely heterosexual audience who danced wildly during the intervals, but Tuesday nights were gay with access only granted to password holders.
It closed after 12 years on 15 January 2005, reportedly to enable its artists to move on to fresh creative pursuits. However, many thought other reasons were that the shows were getting stale, the drag queens were getting old (Kumar was 36) with no fresh blood to carry the torch and the existing ones not having what it took, and the club's poor location. It spawned a spoof version called the Bang Bang Room at Changi Village which held late night performances every weekend.
Desker Road vicinity
A well-known area for men seeking the services of cisgender women sex workers in the Serangoon or Little India area for decades, it attracted many transgender sex workers from nearby Johore Road after the latter was erased from the map by a fire in the late 1990s.
Unlike their cisgender female government-regulated counterparts who are on display, usually seated on armchairs or sofas in well-lit rooms, reminiscent of a low-class back-lane version of Amsterdam, the trans women of Desker Road, in contrast, cruise while standing or strolling. This is done to render their activities, which are considered illegal, less vulnerable to vice squad raids. The seedy atmosphere of the whole vicinity has largely disappeared due to massive redevelopment around Mustafa Centre.
Changi Village has been popular with trans women since the early 1990s and the straight men who go there to ogle at them, chat them up or use their services.
Located on level 2 of the rear block of Orchard Towers along Orchard Road, it is Singapore's second drag queen cabaret nightclub, a joint venture between Kumar, and partner Gwen Khoo, who also owns the 3 Monkeys Restaurant in Orchard Towers. Together, they spent $50,000 to open the venue in July 2005, six months after the closure of Boom Boom Room.
Aiming for the high-end market, Gold Dust boasts professional dancers with flamboyant mardi gras-type costumes, and women dancing alongside drag performers. Kumar's trademark provocative jokes are still the main focus, but now framed in a classier and more streamlined show. Kumar aims to capture the cozy feel and stylish look of New York City-style theatre bars. Thus, the 3,000 sq ft (280 m2) club has no dance floor and all the chairs and tables face the stage. It can hold 180 people, and has the feel of a 1970s glam disco, updated for the new generation. Instead of young National Servicemen and students, who formed a significant part of the Boom Boom Room clientele, Gold Dust intends to target a slightly more upper-crust crowd.
The main aim of the theatre bar is to showcase talent. In addition to the cabaret dances and stand-up comedy staples, it is considering expanding the shows to include mime, monologues, plays and singing. Partner Kumar decided to open the venture because he needed a steady income stream, as well as a home base for his stand-up performances. Although the bar is located in the back block of Orchard Towers where Harry's Bar and Jason's supermarket reside, some felt that the idea of a bar next to the infamous '4 floors of whores' may not appeal to some patrons. However, Kumar felt that Orchard Towers was always known to be a controversial place, and since he was also a controversial performer who pushed the boundaries, it made sense for the bar to be based there.'
For the first time, Kumar's show incorporates two female professional dancers, Samantha Kan and Aslinda. There were only male dancers at the Boom Boom Room. He always felt that the latter was lacking something and now he realised that it was girls.
Chinatown Caberat is a drag queen cabaret opened in 2006 by entrepreneur Max Lim at Ann Siang Hill.
- SgButterfly ,  – Singapore's first and largest transgender web portal and support group founded by a heterosexual man, Daniel Kaw.
- SgGurls ,  – Singapore's second trans woman support group which seeks a higher social profile and aims to reach out to mainstream society.
- Sisters in Solidarity  – a trans woman support group formed by Marla Bendini and Tricia Leong in 2009 to combat discrimination against transgender women in Singapore.
- The Sons – Singapore's first trans men's support group, founded by Joe Wong, "The Sons" shares information, resources and advocates for the well-being of trans men in Singapore.
There is far less information available on trans men in Singapore.
- See also, A first-person account of Bugis Street in the 1950s by Bob, a visiting Australian sailor:
- "Singapore gay films". Archived from the original on 22 June 2006. Retrieved 28 September 2005.
- Sisterhood by Leona Lo (Select Books, 2003, ISBN 981-04-7198-X)- a personalised emotional exposé of the local transvestite and transsexual community by an intellectual trans woman herself.
- My Sisters: Their Stories by Leona Lo and Lance Lee (Viscom Editions Pte Ltd)
- Cries from Within by S. Shan Ratnam; Victor H. H. Goh and Tsoi Wing Foo- a tome on sex-reassignment surgery and its attendant psychological considerations by two eminent gynaecologists and a psychiatrist.
- "The Mak Nyahs: Malaysian Male to Female Transsexuals" (Singapore: Eastern Universities Press, 2002, viii + 175pp., ISBN 981-210-209-4) – a large body of information on the Malay transgender, transvestite and transsexual communities amassed by sociologist Teh Yik Koon from the School of Social Development, University Utara Malaysia.
- Transgender SG: a homegrown resource for transgender people in Singapore]
- Yawning Bread's account of Singapore's transgender and sex-change history: 
- Transgender People In Singapore