Getai performances are usually associated with the afterlife but five new shows hope to get people looking at death in a new light.
The shows in Mandarin will address topics like end-of-life care and encourage audience members to broach the subject with their families.
"We are all going to die. The question is how we are going to (deal with) it," said Lien Foundation chief executive Lee Poh Wah.
The foundation is one of the organisers of the initiative, which is called Die Die Must Say.
He added: "If we are not able to talk about it, how are we going to deal with it effectively?"
The getai shows start on Sunday in Chinatown's Kreta Ayer Square and move to a different heartland neighbourhood each week.
They will be hosted by getai veterans Wang Lei and Lin Ruping and are expected to draw a crowd of more than 10,000 in total over the five weeks.
"For older Singaporeans, getai has tremendous persuasive power," Mr Lee said. "Through dark humour and by poking fun at it, we hope to dissect the topic for our audiences."
Typically, getai shows feature lively exchanges between hosts that can border on the risque.
The organisers also hope to attract young adults.
"It's not uncommon for children to stop their parents from talking about death," said Mr Ang Ziqian, founder of the Ang Chin Moh Foundation.
The organisation, set up by Ang Chin Moh Casket, collaborated with the Lien Foundation in organising the shows.
"Many seniors actually want to have more information, but their family members just brush them off," added Mr Ang.
He recalled how two brothers agonised over their late father's funeral because they had never asked him about his death wishes while he was still alive.
"I could see the regret on their faces," Mr Ang said.
"But this is something we can prevent if we start to talk about death early."
As part of the campaign, voluntary welfare organisation Care Corner will also extend its phone counselling service to those who need to talk about end-of-life issues, a move that will remain in place even after the getai performances end next month.
"We recognise the depth of need confronting our ageing population today," said Care Corner Counselling Centre manager Jonathan Siew.
"We want to lend a listening ear... to the elderly, caregivers and anyone who is grappling with the possibility of death and wanting someone to talk to."