In the history of Singapore gay theatre, it was only in the second half of the 1980s that gay writers started to explore the hitherto taboo area of homosexuality in their works. The licencing authority, however, was not quite ready so that in 1988, 3 plays with gay themes were banned from being performed. These were Eleanor Wong's "Jackson on a Jaunt", Chay Yew's "As if He Hears" and Russell Heng's "Lest The Demons Get To Me". The first two plays were subsequently staged in 1989/1990 after negotiations with the authority. The third was staged in 1992 after Singapore's culture policy was liberalised by its new Prime Minister, Goh Chok Tong.
The following are some of the local theatre productions which have featured cross-dressing or LGBT themes:
M Butterfly is an internationally acclaimed theatre piece by Chinese-American playwright David Hwang about a transvestite male opera star’s deceptive seduction of an unsuspecting French male diplomat in China. It was staged during the 1990 Singapore International Arts Festival in the wake of the proscription of 3 gay plays just 2 years earlier, probably to symbolise newly-appointed Prime Minister Goh Chok Tong's vision of a "kinder and gentler Singapore". It also marked the first instance of total nudity in Singapore theatre. The impact was heightened by the local media which, habitually sensitised to the political climate, highlighted members of the political élite seated in the front row taking in the spectacle with cultured nonchalance. 
The Gunung Sayang Association's Peranakan playsEdit
Kenny Chan is a comedic performer from Melaka who has also played the matriarch role and is known for what some consider rather crude stand-up comedy acts. Chan was most recently seen as Romeo in the TV12 series, "The Ways of the Matriarch".
- Menyesal- Regret
- Buang Keroh, Pungot Jernih- Let bygones be bygones
- Zaman Sekarang - These modern times
- Jackson on a jaunt
- As if he hears*
- Lest the demons get to me*
- Emily of Emerald Hill*
- An Occasional Orchid*
Invitation to treatEdit
Invitation to treat (play) is a month-long trilogy of plays performed at the Jubilee Hall, Raffles Hotel in April 2003. They were penned by acclaimed playwright and academic lawyer Eleanor Wong and produced by W!LD RICE, a professional theatre company founded by well-regarded Artistic Director Ivan Heng. 
The three plays of Invitation To treat spanned 20 years in the life of their protagonist, Ellen Toh, following her journey towards self-discovery and self-actualisation. She was a smart, ambitious and hardworking lesbian lawyer who married her best friend in a 'marriage of convenience' that presented her with the best of both worlds– a socially respectable position, and a husband who accepted her sexual orientation.
The plays swept the audience along a unique and enjoyable journey, an Odyssey of insights which recounted the story of one member of an invisible minority who struggled with her sexuality and, over time, grew increasingly confident and self-aware, with more than a little help from her friends. Heng hoped that the LGBT community would relate to the plays which included 'insider' jokes and references that could only be fully appreciated by the gay community, with scripts that were not dumbed down to accommodate a straight audience. Owing to its lesbian theme, the producers experienced great difficulty in securing a corporate sponsor.
- Mergers & accusations. Examined personal choices and living in transition while dreaming of, hoping for, and wanting, the 'perfect' future. 
- Wills & secession. Explored the corridors of the past, and unravelled the bonds of family and faith in the face of disease and death. 
- Jointly & severably. World-premièred from 9 to 26 April 2003, the play laid bare the struggle for commitment, exploded the meaning of family, love and friendship, and the right of a minority to live and love honestly and fearlessly. 
The play Private Parts was premiered at the 1992 Singapore Arts Festival, generating a buzz that lasted well past its two sell-out seasons, both during the festival and its immediate rerun, when it played to an estimated audience of 20,000.
Many felt that Private Parts was popular playwright Michael Chiang’s best play to date; definitely, it was his most politicised. The man who defined Singapore comedy with runaway hits like Army Daze, Beauty World and Mixed Signals, surprised many with this pointed yet poignant piece of writing.
Pushing the envelope the way no other local production had ever done, Private Parts was a play many agree was ahead of its time. One gets involved with a talk-show host who soon finds out the true meaning of reality TV. One gets a glimpse of the brutality of media competition: how far would one go for higher ratings? Plus, for a nation of gawkers weaned on the night-time beauties of Bugis Street back in the 60s, here was an up-close peek into that mysterious world of drag queens. What more could one want from theatre in the rigid, pre-RA days of Singapore?
Hype aside, Private Parts made news because it was able to engross even the most conservative of audiences with its bittersweet (and unexpectedly moving) story about 3 transsexuals trying to find their place in life. Way before Hollywood was fêted for daring to do the same by putting Terence Stamp, Guy Pearce and Hugo Weaving in heels and makeup for Priscilla, Queen of the Desert (1994). Not to mention Patrick Swayze, Wesley Snipes and John Leguizamo donning even bigger bouffants and bosoms in To Wong Foo, Thanks for Everything (1995).
The story: Briefly, a Star Search winner fronts a current-affairs talk show to improve ratings. His life turns upside down when he ends up in a sex-change clinic with 3 transsexuals. After befriending them, he tries to get them on his show.
Private Parts proved to be such an audience favourite that it was revived in 1995 for another run, this time including a Mandarin version (which starred Edmund Chen and the late comedian Hua Liang) as well!
And 12 years on, Michael Chiang’s much-acclaimed play returned to the Singapore stage for a limited season, to wow new audiences, and hopefully bring back some of its old supporters. The new, updated production had its run at the Esplanade Theatre from 28 July to 1 August 2004. 
- Mardi Gras
- Top or bottom
- Asian boys Vol. 2
- Autumn Tomyam
- Beautiful thing
- White sails over blue blue sea
- East Side story
A unique one-woman show on 17 and 18 June 2005 by Parinya Charoenphol, also familiarly known in Thai as Nong Thoom. The famous former Muay Thai (kickboxing) champion who stunned the world with her gender change invited the audience into her colourful world where strength meets beauty, fight meets dance and heart meets mind. 
Spirits 'Yao Jing'Edit
It world-premièred on 3 June 2005 at the Victoria Theatre and Concert Hall.  Written as a special dedication to Toy Factory's 15th anniversary and directed by award-winning director Goh Boon Teck, it recounted once upon 5,000 years ago when 5 ill-fated beauties were impeached for their tramped existence. Spirits unveiled 5 untold stories of Sai Jing Hua from the Qing dynasty, an infamous prostitute, Bao Si from the Zhou dynasty, the concubine who never smiled, Lu Hou from the Han dynasty, the revengeful empress, Ya Zuan Ji from the Tang dynasty, a poetic priestess and Ke Shi Ming from the Ming dynasty, the Great Madam, all of whom were despised and condemned by Chinese historians.
Goh collaborated with playwright Xu Sheng Liang (China) and music composer Saidah Rastam (Malaysia) to reinterpret Chinese opera and its heritage in a different ensemble. Together, they breathed contemporary life into traditional Chinese opera whilst retaining its beauty.
It was crafted as a musical, infusing 5 different forms of Chinese opera, namely Yue, Jing, Li Yuan, Huang Mei and Yu, with contemporary funk. No traditional opera musical instruments or props were employed in this unconventional fusion. Instead, there were 4 actors, 5 martial artistes, 7 musicians, 1 saxophonist and 5 genres of opera in this creative mix.
Spirits advanced Chinese opera a step forward, creating a new theatre platform for the younger generation. Multimedia effects and high-tech neon swords replaced traditional props. An outrageous wardrobe dazzled and a fascinating mobile stage transported the audience to another world.
The constantly challenged notion of masculinity in Asia has unfortunately led to the near extinction of opera female impersonators. Toy Factory proudly featured 5 of these professional 'Nan Hua Dan' from Singapore and China, which made the musical drama all the more gripping.
A project by Richard Chua, after Lover's Words, about heterosexuals in a homosexual society. It was an extension of Chua's belief that life should be led honestly and truthfully. In his quest to further meditate on love between people (in this case, among 3 boys in their 20s), Chua embarked on this project to push his collaborators to work in a space where they had nowhere to go, but to clean.
Cleaning was an essential task that would bring these boys to the next phase of eternity. The story was about love - love that seemed to be defined differently by different people, with different perspectives, resulting in different outcomes. Each boy had a love story to tell.
The following theatre companies have been active in staging plays which examine LGBT issues:
- The Necessary Stage.  A major theatre company which produced Mardi Gras  and Top or Bottom .
- It has existed for more than a decade, its history recently documented in the book Ask Not: The Necessary Stage in Singapore by social activists Dr. Tan Chong Kee and Tisa Ng.
- Action Theatre. Straits Times' Life! theatre award winner for gay-affirmative plays such as Autumn Tomyam , and producers of the movie Beautiful Boxer. 
- Toy Factory Theatre Ensemble. A leading Chinese-English bilingual drama company and another Life! theatre award winner, tremendously and publicly gay-affirmative. It produced Bent , staged and translated Beautiful Thing  , wrote the original script for White Sails Over Blue Blue Sea  and East Side Story on the love between two ah beng gangsters. Its recent offerings were Porcelain by acclaimed Singaporean playwright Chay Yew and Spirits 'Yao Jing', a novel interpretation of Chinese opera. It provided assistance to Threesixzero Productions in its production of a well-balanced documentary for MediaCorp TV on Channel U entitled 'Do homosexuals have space for their activities?' as part of the 'Very Penetrating Insight' series in 2005.
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