The nominees for Best Supporting Actor have tackled diverse roles that cross gender, religious, racial and even ethical lines.
Debates about religion, sometimes entering uncomfortable territory, are explored in roles such as Ahmad, the Muslim funeral director who confronts a lesbian in Hatch Theatrics' Hawa. He is played by Saiful Amri Ahmad Elahi.
Ghafir Akbar's Abe, in Singapore Repertory Theatre's explosive play Disgraced, also confronts this in the light of a religious awakening in post-9/11 New York.
Lian Sutton breaches gender lines in Cake Theatrical Productions' Electra - playing both a murderous woman and her heroic son.
Rei Poh's multiple roles in Grandmother Tongue by Wild Rice bring to the fore the struggle to communicate with one's elders as the use of Chinese dialects wanes.
And, lastly, seasoned actor Adrian Pang strikes up an ethical debate in the medical field in Pangdemonium's staging of a love story set in a research facility, The Effect.
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Best Supporting Actor nominees
Adrian Pang, 51
Nominated for: The Effect (Pangdemonium)
Previous nominations: 11 nominations for Best Actor, including for Frozen (Pangdemonium, 2015) and The Full Monty (Pangdemonium, 2011); two nominations for Best Supporting Actor, including for Forbidden City (Singapore Repertory Theatre, 2003)
Previous wins: Four Best Actor wins, including for The LKY Musical (Metropolitan Productions; Singapore Repertory Theatre, 2016) and Rabbit Hole (Pangdemonium, 2014)
It is hard to imagine, but Adrian Pang is terrified of giving speeches when it is not part of a role. "I am very uncomfortable standing in front of an audience speaking as myself. It makes my skin crawl. It fills me with terror."
This was one way in which he differed from his role of showboating doctor Toby Sealey in pharmaceutical play The Effect. In one scene, he gives a highly crafted speech and relishes the audience's reaction when he wields a human brain in front of them.
The play was staged by Pangdemonium, the theatre company he set up with his wife, Tracie Pang. It is written by British playwright Lucy Prebble.
Pang says he is "very surprised" with the nomination, as he felt the character was more of a plot device for Prebble to open up the debate about whether depression can be medicated away.
In the play, actors Linden Furnell and Nikki Muller play a couple who fall in love while on medication. Playing opposite Pang was Tan Kheng Hua as Dr Lorna James, who worries about the ethical aspects of their medical study.
"In the bigger scheme of things, his function was to offer that side of the debate about the ethics of big pharma. The beauty of the writing was that the debate was so fiery and emotional, yet intellectual at the same time."
Saiful Amri Ahmad Elahi, 39
Nominated for: Hawa (Hatch Theatrics/Wild Rice's Singapore Theatre Festival)
Previous nominations: Two for Best Ensemble including for Ziarah (Teater Ekamatra, 2010)
Previous wins: One for Best Ensemble for Bilik Ahmad (Teater Ekamatra, 2009)
Saiful Amri Ahmad Elahi plays Ahmad, a business- minded funeral director in Hawa by Hatch Theatrics, written by Johnny Jon Jon. In the play, Ahmad meets Siti (played by Koh Wan Ching), a Muslim convert who is holding a funeral for her loved one, but he is more interested in the money-making aspects of the transaction.
"I hope not to meet a character like him," he says with a laugh. "But there are such people in real life."
Saiful reprised the role from a 2015 staging, alongside actor Al-Matin Yatim, who plays religious romeo Zaki. Siti was played by Isabella Chiam in that staging.
Saiful had to learn to perform the Muslim funeral rites for the play. In it, he demonstrates, using Zaki as a model, how to wrap the body in a kain kafan, or white cloth used in funerals.
To learn to do this, he consulted a friend who performs such rites.
The scene had a profound effect on the audience. Some cried and Saiful recalls one person walking out in the 2015 staging, which he said affected him quite a bit.
"Playing that role and discovering the beauty of it, of wrapping the body - although it's just a body and the soul has already gone, you still have to prepare the body properly. It's a big responsibility."
Rei Poh, 36
Nominated for: Grandmother Tongue (Wild Rice/ Wild Rice's Singapore Theatre Festival)
Previous nominations: Five for Best Ensemble, including for Home Boxes (Paper Monkey Theatre, 2011)
Previous wins: One for Best Ensemble for Twelve Angry Men (Nine Years Theatre, 2014) Grandmother Tongue by first-time playwright
Thomas Lim is about a young man (Tan Shou Chen) who has trouble communicating with his Teochew-speaking 84-year-old grandmother (Jalyn Han).
But actor Rei Poh's take on seven minor characters in the play - including a doctor, the man's late grandfather and a schoolmaster - was not lost in translation.
Of all these, he says it was most challenging to portray a Filipino nurse, who takes care of the grandmother when she has a fall, because he is "bad at accents".
He had to keep practising to be convincing, but more importantly, he did not want to play a stereotype. "I made sure I wasn't just putting on an accent. It wasn't a caricature of the character, but about her actions," he says.
The Teochew dialect also tripped him up. All three cast members took Teochew lessons with a teacher as part of rehearsals, but Poh is the only Hokkien speaker.
Hokkien has similarities to Teochew. Poh describes himself as having a "Hokkien baggage" and at times falling back on the Hokkien pronunciation of words. But, thankfully, his teacher saw the practical side of this.
"He was, like, 'Okay, never mind, nowadays there's a lot of mixture in the use of the two dialects. It's okay to use the Hokkien intonation sometimes.'"
Ghafir Akbar, 35
Nominated for: Disgraced (Singapore Repertory Theatre)
Previous nominations: Three nominations, including Best Supporting Actor for Public Enemy (Wild Rice, 2016) and Best Ensemble for Another Country (Wild Rice, 2016)
Previous wins: Best Ensemble for Hotel (Wild Rice, 2016)
Kuala Lumpur-based actor Ghafir Akbar plays Abe in Disgraced, a Pulitzer Prize-winning play by Pakistani- American playwright Ayad Akhtar. The Muslim youth, nephew to protagonist Amir (played by Gaurav Kripalani), goes through a religious awakening in the story. The Starbucks-drinking New Yorker changes his name from Hussein to Abe in the name of assimilation, but later turns into a religious fundamentalist.
Religious fervour aside, Ghafir says he could relate to Abe's feelings of being an outsider. He lived in the United States between 2004 and 2012 - in Michigan and Florida for school and then New York for work.
"When I first moved, I felt I needed to be American because it was the only way people would accept me," recalls Ghafir.
Even in cosmopolitan New York, he was racially profiled as an actor. "I was always seen as 'Terrorist No. 5'. It got me thinking about how I was being perceived."
He is proud of the play for its unflinching take on prickly issues about race and religion. He says: "I look at the nomination as recognition not only of my work, but also of the play and what it's trying to say."
Lian Sutton, 25
Nominated for: Electra (Cake Theatrical Productions)
Previous nominations: None
Previous wins: None
In Cake Theatrical Productions' re-imagining of the classic Greek revenge play Electra, Lian Sutton played both a villain and a hero.
He was Clytemnestra, Electra's mother who plots to murder her husband and has a strained relationship with her daughter. At the same time, he was also Electra's brother Orestes, the prodigal son who is brought up to exact revenge for the murder and ends up murdering his mother.
Sutton recalls that it was challenging to play two roles who were so different from each other.
"It was like a juggling act. There would be times when I would be close to (portraying) Clytemnestra, then I would start to lose Orestes," he says.
"Then we had to bring that machismo, that angry young man out again."
Actress Edith Podesta played Electra, while Sutton and fellow actors Sharda Harrison and Andrew Marko took on multiple roles in the production directed by Natalie Hennedige.
This is Malaysia-born Sutton's first nomination at the awards and he gives credit to Hennedige for casting him in the show.
He says: "There's no one else who would put so much faith in a millennial foreign talent like me to play a mother from a completely different generation - one of the strongest female roles in theatre."