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After Mayor Rob Ford's appearance on Jimmy Kimmel Monday night, Doug Ford told a friendly newspaper columnist, Joe Warmington of the Toronto Sun, that his brother was "a little upset" over the questioning he got on the show.

Which makes you wonder: what did he expect? Mr. Kimmel is a comic. Mockery is his stock in trade. He has been making fun of Mr. Ford regularly and gleefully for months.

Mr. Kimmel himself couldn't help but wonder why on earth the mayor had agreed to subject himself to the comedian's tender mercies. "Why are you here?" he asked. "What good could come of this? Have you ever seen the show?"

Mr. Kimmel ended up devoting what was, by TV standards, an extraordinary amount of time to our man – three full segments of air time. He mocked him thoroughly, but not in a mean way. He asked some tough questions, tougher than Mr. Ford sometimes gets from interviewers back home. He ended with a serious suggestion for an embarrassed-looking, red-faced Mr. Ford – you might want to get some help.

It was an impressive performance from the late-night guy, who managed to be probing, funny and sympathetic all at once. Mr. Ford, on the other hand, missed a chance to show a frank and human side. After managing to laugh his way through most of the jokes in an aw-come-on, gimme-a-break sort of way, he went straight into his campaign pitch, repeating familiar boasts about how many calls he has answered and how much money he has saved taxpayers.

He didn't hesitate to trot out his discredited claim about a billion dollars in savings to a skeptical Mr. Kimmel. "I've got a proven track record of success," he told his host. He even offered the address of his campaign website, as if he were on a North York cable show instead of a North American broadcast.

Mr. Kimmel was unrelenting. He suggested that it might not have been the cleverest thing for Mr. Ford to dare the chief of police to arrest him. He read out a list of angry things that people in Toronto were saying about the mayor, including the suggestion that he was homophobic (Mr. Ford denied it).

He took Mr. Ford over to a video screen and got him to watch a few of his greatest hits, including the Steak Queen video, the Pam McConnell tackle video, the death-threat rant and even the one where Mr. Ford throws great heaping handfuls of candy at kids watching a parade. Mr. Kimmel seemed to enjoy that one most of all, with the possible exception of the one where Mr. Ford play acts at drunk driving to make fun of a city councillor. (Mr. Kimmel: "Were you classically trained in pantomime?")

Mr. Ford had little to say. When Mr. Kimmel asked who he was threatening to kill in the rant video, he said, implausibly, that he simply didn't know.

The moment of truth came in the last segment when Mr. Kimmel, turning earnest, said that Mr. Ford seemed like a nice guy and gently suggested that he needed someone to talk to. "If you're drinking enough that you can try crack in your 40s and you don't remember it, maybe that's something that you might want to think about."

But Mr. Ford simply threw his head back to laugh when Mr. Kimmel used the word "alcoholic" and deployed one of his standard deflections: "I wasn't elected to be perfect Jimmy. I was elected to clean up the mess I inherited."

A different man might have made something out of this appearance, as risky as it was. Many viewers would have given him some credit in the first place for being a good sport and stepping into the firing line. A little candour, a little contrition would have gone a long way. Just some sign of awareness about his position and his own role in putting himself in it would have been welcome. But Mr. Ford seems beyond that.

He seemed to think Mr. Kimmel was his buddy and that buddies don't ask hard questions. Real buddies do, of course, and Mr. Ford shouldn't have been surprised to find himself the subject of this friendly but forensic late-night grilling.

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