Photos by Sharon Steele – Down with Webster originally started as an instrumental jazz band that was formed in a music class at Glen Ames Senior Public School in 1998 by band members Patrick Gillett and Tyler Armes. They, along with the original members of the band, quickly named the group toward the end of class after the beloved titular character from the 80s sitcom Webster, who is played by Emmanuel Lewis. Following a victory at their school’s “Battle of the Bands” competition, the group was joined by Andrew Martino and Martin “Bucky” Seja, students from Cardinal Carter Academy for the Arts, and other members who attended Malvern Collegiate Institute. As a jam band, they made reggae, funk and jazz inspired music in Armes’ father garage. Hip-hop elements were incorporated into their music once Seja became a part of the group and rapped along with Gillett, who also brought an influence of blues rock to the band.

The band released a six-track CD-R EP titled The Reverb Session July ’03. This release was primarily sold at concerts in 2003 and 2004. Hype man Kyle “Kap” Fairlie, a former actor whose voice work includes roles in the Nelvana series Redwall, Franklin, Babar and Rolie Polie Olie, and the film The Little Bear Movie, and rapper Cameron “Cam” Hunter would later join the band’s lineup. In 2007, the band released their debut independent self-titled album.