Toronto's radio landscape is losing one of its most distinctive voices as legendary broadcaster John Oakley prepares to host his final afternoon drive show on AM 640 this Friday, November 26, 2025.
The announcement has sent shockwaves through the Canadian media industry and among loyal listeners who have followed Oakley's career across multiple decades and stations.
A Broadcasting Career Spanning Generations
John Oakley's radio journey represents nearly half a century of dedication to the airwaves. His current position has him hosting the critical 3 p.m. to 6 p.m. afternoon drive slot, but his influence stretches back much further.
Before his decade-long afternoon show, Oakley was a morning show stalwart following extensive experience in nighttime radio across Orillia and Montreal. His Toronto breakthrough came at CFRB, now known as Newstalk 1010, before he made the pivotal move to AM 640 in 2003.
His morning show years began each day at 6 a.m. with his signature opening - the famous bell and Chuck Berry's Johnny B. Goode theme song that became instantly recognizable to Toronto listeners.
The Oakley Show Formula: Controversy and Conversation
What set Oakley apart in Toronto's competitive radio market was his commitment to unfiltered discussion and diverse perspectives. His shows became known for bringing together panels featuring voices from across the political and cultural spectrum.
Regular guests included controversial figures like disbarred lawyer Harry Cupido, sports betting expert Cam Stewart, and commentators ranging from Charles McVety to Pastor Greta Vosper, David Menzies, Susan G. Cole, and Joe Fiorito.
The show also featured unfiltered former Toronto Sun columnist Sue-Anne Levy and Ezra Levant, creating what many described as electric radio that pushed boundaries while maintaining thoughtful discourse.
Behind the scenes, Oakley worked with talented producers including Richard Syrett, Victor "The Machine" Machado, Lyndsey Vanstone, and Michael J. Downey, who helped shape the show's distinctive character.
The Rob Ford Era and Political Impact
Perhaps one of Oakley's most significant contributions to Toronto's political landscape was his role in the rise of Rob Ford. Before Ford became known internationally as Toronto's crack-smoking mayor, he was a grassroots councillor from Etobicoke North who found a platform on Oakley's show.
Ford's weekly Thursday segments became must-listen radio as he detailed what he described as wasteful spending at City Hall. Years of these regular appearances helped build the foundation for Ford's successful 2010 mayoral campaign.
Following his victory, Ford chose Oakley's show for his first interview as mayor-elect, with dozens of reporters and cameras documenting the moment. The relationship continued throughout Ford's tumultuous time in office, with Oakley maintaining a balanced approach that acknowledged Ford's flaws while recognizing his humanity.
Ford once credited Oakley not only with helping him become mayor but also with supporting his eventual journey to sobriety during the final year of his life before his tragic death from cancer in 2016.
Memorable Moments and Lasting Legacy
Oakley's career has been marked by memorable interviews and occasional confrontations. Environmentalist David Suzuki famously walked out of an interview after facing questions about his gas-powered bus idling at events where attendees were criticized for fossil fuel use.
Yet Oakley never held grudges, maintaining an open microphone policy for all perspectives. His ability to expose hypocrisy while maintaining professional relationships became one of his trademarks.
This final week of shows has featured nostalgic looks back at career highlights, including stories from Earl McRae about Elvis supposedly living in Tweed and memorable banter with comedy legend Jerry Seinfeld.
While no specific reason has been given for Oakley's retirement, his approach during this farewell week suggests this is a planned retirement after nearly 50 years of dedicated work. However, as with sports legends like Gordie Howe and Guy Lafleur, retirement may not be permanent, leaving open the possibility of Oakley's return to broadcasting in some capacity.
For now, Toronto media watchers and loyal listeners prepare to say farewell to a broadcasting icon whose voice has been part of the city's daily soundtrack for generations. His final sign-off from the AM 640 microphone is scheduled for 6 p.m. this Friday.
