Mathews formed The Watchmen in 1989 with his Anglo Chinese School classmates Tony and James Makarome.
A track from the EP, "I Love Singapore", was later included on the Mee Pok Man movie soundtrack, with Mathews going under the nom de plume of "The Crowd".
In April 1994, Mathews' Watchmen bandmates Tony and James Makarome wrote an open letter to the press accusing him of failing to acknowledge their contributions.
[2][3] In 1998, Mathews formed Popland, a musical duo between him and British-born bass player, Tim Nolan.
In November 2008, he released the EP watchmen@midnight and his debut solo full-length album Emo FASCISM on 1 August 2013.
Mathews has been a live performer for more than thirty years and has performed at Central Park NYC (for Singapore Day 2007), the Esplanade, *SCAPE, Home Club, Blu-Jaz Cafe, Library @ Esplanade, Library @ Orchard, Timbre @ The Substation, Timbre @ The Arts House, TAB, the Prince of Wales Backpackers' Pub and other venues.