Rock quintet The Great Spy Experiment and singer-songwriters Inch Chua and Charlie Lim are the artists who have the honour of fronting this laudable bold move made by their record label, House Of Riot.
The gambit throws down the gauntlet to indie musicians to aim big.
"Watching the House Of Riot show shouldn't be any different from watching, say, The xx at the Esplanade Concert Hall," says House Of Riot founder Mike See, referring to the Mercury Prize-winning British band which played at the venue in 2010.
He adds that the show is the company's biggest undertaking to date and that no expense has been spared to ensure the audience gets a high-quality show.
See started the company as Riot! Records with The Great Spy Experiment in 2007, and it has now expanded to a trio, with See's wife Eugenie Yeo and Sarah Sim helping in marketing and other roles. The label added Chua and Lim to its roster in 2012.
Lim, Chua and The Great Spy Experiment are no strangers to massive concerts, having cut their teeth on local gigs as well as regional and international music festivals such as South By Southwest (SXSW) in the United States.
They have also performed at the Esplanade's other venues, both ticketed (the 245-seat Recital Studio and 220-seat Theatre Studio) and free (the 600-capacity Outdoor Theatre and music festival Baybeats' makeshift, open-air Powerhouse stage).
But the Esplanade Concert Hall, with its 1,600 seats and world-class acoustics, is a different beast altogether, having hosted stellar acts from jazz luminary Wynton Marsalis to classical star Joshua Bell.
Home-grown indie acts who have played sets there have done so only as supporting acts to foreign ones. One such group is roots-rock band Cheating Sons, which opened for Irish indie band Two Door Cinema Club in 2011.