The original group was formed in 1995 in Toronto by four high school friends, Julian Taylor (JT), David E.G. Marshall, Dan Black and Jeremy Elliott. The group quickly gained a local following in North Toronto with frequent performances at the Corner Café and Mad Monty’s. They recorded their first EP, Mold, in 1996 with Toronto musician and producer Darrell O’Dea.
In 1997 Marshall left the group. They re-formed the line up by adding producer/multi-instrumentalist Darrell O’Dea and guitarist Bruce Adamson after they met at the Rose & Crown open stage hosted by Doug Courtice and the Crown Jewels. Staggered Crossing built their reputation in venues such as Lee's Palace, the Horseshoe Tavern, Reverb, the El Mocambo and countless others Toronto establishments.
In 1997 record executive Frank Davies—a Canadian industry legend who launched the careers of Tom Cochrane, Crowbar, A Foot in Cold Water and dozens of others— signed the group to The Music Publisher (TMP) after his daughter had given him a copy of Mold. Between 1997-99 almost 40 songs were written and demoed by the group.