Stroumboulopoulos was born in Malton, Ontario, a neighbourhood in Mississauga, Ontario, to a Greek father from Egypt and a Ukrainian mother. He was raised in Toronto, primarily by his mother and a close-knit extended family. After graduating from Ascension of Our Lord Secondary School, he briefly studied radio broadcasting at Toronto’s Humber College.
In spring 1993, Stroumboulopoulos worked at rock radio in Kelowna, British Columbia for a few months before getting a job offer at the Toronto radio station Fan 590 AM, working in talk radio. He then moved to CFNY-FM to host various shows including Live in Toronto.
From 2000 to 2004, Stroumboulopoulos worked at MuchMusic as producer and host of The Punk Show, then host of The NewMusic, MuchLOUD and MuchNews.

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