From 1999 to 2005 he was a morning host at the highly successful (citation needed) KISS 92 FM and CHFI in Toronto. His first co-host at KISS was Daryn Jones. With Jones' departure to focus on television, he was paired with Billie Holiday. When the plug was pulled on the pop format at KISS in June 2003, their program, eventually renamed Jay and Billie, continued for two years at sister station CHFI. After a year-long absence from the dial, Mad Dog and Billie returned to the Toronto airwaves on August 8, 2006. In 2011 The show was rebranded Mad Dog and Maura.
Michaels was fired from Virgin Radio after hosting his morning show on March 4, 2015.