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I was thinking of Terence Corcoran, but he's easily surpassed by some of the names mentioned in the past few posts.

Believe it or not, Terry Corcoran is actually a really nice guy. I worked with him for a few years, and he's nothing like the character he puts on for his columns. He's kind of quiet, very funny and considerate/respectful of other points of view, even when he doesn't share them. There are a lot people around who scratch their heads over the difference between the man and the columnist. But, oy, some of the columns. Yikes!
 
Top Ten Assholes:

1: Rob
2: Doug
3: Frank D'Angelo
4: Mammo
5: Sue Ann Levy
6: Wormington
7: Denzil Minnan-Wong
8: Brad Lamb
9: ....

I'm drawing a blank on the last two. Any suggestions?

While he deserves a higher spot than 9 or 10, the list is not complete without Ezra Levant.
 
Believe it or not, Terry Corcoran is actually a really nice guy. I worked with him for a few years, and he's nothing like the character he puts on for his columns. He's kind of quiet, very funny and considerate/respectful of other points of view, even when he doesn't share them. There are a lot people around who scratch their heads over the difference between the man and the columnist. But, oy, some of the columns. Yikes!

He does a very convincing impression of a condescending asshole in his columns. He should have been an actor, by the sound of it.
 
I recall Robbie saying his favourite band is Triumph which is far more egregious than the crack smoking.

Triumph's drummer Gil Moore is known for owning Metalworks Studios in Mississauga, as well as for being pals with such right-wing luminaries as Tim Hudak and the FoFam.

ETA: The video in the second link below is worth watching just for the fact that "Hudak repeatedly dodges the question, eventually giv[es] up and awkwardly walk away from the event", and for the reporters' chatter right at the end, after the walkout.

~~~

"Triumph Drummer and Metalworks Founder Gil Moore joined Toronto Mayor Rob Ford and Councilor Doug Ford to help rock out on the first birthday of The City with Mayor Rob Ford , their weekly Newstalk 1010 Radio Show."

http://triumphmusic.com/blog/gil-moore-visits-the-city-radio-show-with-mayor-rob-ford/

"Tim Hudak blunders campaign kick-off over music funding track record."

"Global News has posted a video of Ontario PC leader, Tim Hudak’s campaign kick-off which took place at the legendary Metalworks Studios in Mississauga, Ontario. The irony was not lost on the reporters, who recalled his voting against the $45 million Ontario Music Fund in last years 2013 budget, describing it as "corporate welfare"."

http://www.musicaltoronto.org/2014/...ign-kick-off-over-music-funding-track-record/
 
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While he deserves a higher spot than 9 or 10, the list is not complete without Ezra Levant.

How about top ten Asshole Toronto Families?

1. The Fords
2. The Nunziatas
3. ...

And a top ten Annoying Toronto Families (not necessarily jerks but waaay overexposed)

1. The Olivers
2. The Lastmans
3. The Wright Sisters
4 ...
 
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He does a very convincing impression of a condescending asshole in his columns. He should have been an actor, by the sound of it.

No kidding. I get especially peeved/enraged about his "junk science" schitck (like his climate arguments have any merit. Sheesh!) On the other hand, I always have a good time when I talk to him. I remember a Sunday afternoon a few years back. Terry and I were both at the office and having a bit of chat about writing columns and how columnists take on a persona that may only have the barest connection to their actual personality. Terry said that he had no idea what he'd do with himself if he wasn't writing his column. I told him the answer was simple: he'd been one of those ranting cranks who spends all day writing letters to the editor. Terry got a good laugh out of that.
 
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