Performing alongside Jason Barr (another holdover from the "Humble & Fred" show where he had worked as producer after also starting out as intern, performing promotional stunts in fake Scottish accent under the Danger Boy pseudonym), Shapiro became one of Blundell's two sidekicks. The station also had Sandra Plagakis periodically coming on throughout the morning to read news and traffic reports and the three show hosts would occasionally engage her in a conversation. Shapiro's primary role on the show entailed coming up with daily content mostly through puerile and occasionally outrageous behaviour; often referred to as ReTodd on the air, his signature segment 'Todd on the Street' involved talking to homeless people on the streets of Toronto in a manner many found to be malicious, offensive, and exploitative. His other notable moments from the show had him visiting his grandmother in her old-age home live on air for a round of juvenile questions about her sex life, walking around Union Station wearing only an adult diaper, and sneaking into Toronto hotels to pound on rival hockey players' doors at 6 a.m. before games against the Toronto Maple Leafs.