Mr Kenneth Kwok, assistant chief executive of NAC, says the project is "about the rediscovery of Singapore's rich musical heritage by connecting younger generations with the music of years gone by".
Ten pairs of emerging and established artists were brought together - most for the first time - to rework the original songs. The songs were chosen from a list of 25 by the public, who voted for their favourite Singapore classics in June.
About 16,000 votes were cast, with songs such as Dick Lee's The Mad Chinaman and Humpback Oak's Circling Square among the 10 that made the final cut.
The artists were selected for the range of genres they represented, including indie-electronic, folk, blues, rock, indie rock and pop.
Home-grown musician and producer Tim De Cotta from creative arts curation agency Getai Group worked closely with the NAC to pair the artists and programmeThe Great Singapore Replay.
He says: "The 10 pairs of artists give an excellent snapshot of the diverse and talented local arts scene we have in Singapore. We have a wide range of artists who create music across numerous genres."
When pairing the acts, De Cotta, 31, imagined "how their artist personas and flavours would match the songs we decided to assign them".
"We didn't want to make it too easy and wanted to stretch them artistically, but, at the same time, not making it impossible."
One of the emerging artists, singersongwriter Theodora Lau says the project is a "ballsy move", considering that reinterpreting classics can go "really well or awfully wrong".
"But I was attracted to the challenge," says the 20-year-old, who reimagined Shirley Nair & The Silver Strings' 1960s hit You're The Boy with Ginny Bloop (Eugenia Yip from electronic indie act Riot !n Magenta).
The established acts appreciate the chance this project gave them to connect with Singapore's music history.
Electronic artist Vandetta(who is also known as radio DJ Vanessa Fernandez) is performing the huge 1960s hit Shanty by The Quests with indie band .gif.
She says: "The idea of contemporary musicians looking back at music created by our pioneers is a great process for any musician. There's this solidarity with musicians from where you're from and a connection."
Many of the emerging acts say they also learnt about Singapore's rich music history while working on the project.
Jonathan Pereira, frontman of The Betts, which are performing rock band Force Vomit's cult classic Siti, says: "Before there was the current wave of acts like The Sam Willows and Gentle Bones, there was this entire crazy roster of Singapore acts.
"If not for this project, we would have never heard of a lot of these songs. It's great that now there's a chance for them to be heard all over again."
53A singer Sara Wee, who is performing Circling Square with Joie Tan, hopes The Great Singapore Replay returns next year "with a whole new slate of acts".
"There are so many Singapore songs that deserve this kind of love," she says.
Jason Shahul Hameed, band leader of Gingerbread, whose 1980s hit Roses was reworked by Andrew "Dru" Chen and Umar Sirhan, is humble about his band's contribution to local music history.
The 63-year-old reveals that the song was written by their bass player Moses Vadham after a breakup and admits that it was "a bit cheesy".
"But I know we wrote a good song because it's one that will go on for the next three generations," he quips.
THEODORA AND GINNY BLOOP