The suit that Rob Ford wore was heartbreaking. All black but for a lurid, cartoon red tie and hanky, it was the sort of thing that a 16 year-old boy– a not very popular or savvy 16 year-old boy– might wear when he wanted to make a splash at an event in which he was over-invested and nervous. The suit did not evoke thoughts of the sophisticated big city that the mayor was purportedly promoting, but instead suggested an owner/greeter at an affordable, franchised steak house somewhere in between other places.

It’s actually hard to imagine what was going through Rob Ford’s mind when he chose that suit. Did he think it embodied west coast cool, was perhaps iconoclastic, or did he just really, you know, think it was happening?

Regardless, what was written in the shiny need of that suit and the doomed narcissism that propelled him onto the show, was just how much Ford wants to be accepted. He’s dying to be liked by Kimmel and be a part of that elite, celebrity crew, to finally be a cool kid.  Ford wants to have a bold personality and to lead a big, American life free from compromise or mediation, but he doesn’t have the tools to achieve this dream of myth. On the show, this big try-out for the team, Ford was rejected and mocked. Kimmel, the school alpha, ran easy circles around him as if teasing the slow boy– who would always be wearing the wrong clothes– at recess.

In the rigid late-night format where irony trumps earnestness, it was easy to take Ford apart. Removed from the political arena, where nobody knows what the hell to do with him, and putting Ford under the burning lights of show biz, stripped him of whatever institutional defenses he might have. It was fascinating to watch Ford immobilized beside a video monitor as a host of embarrassing and surreal clips of him played as if from the Ghost-of-Christmas future. After each segment Kimmel would make a witty observation or ask a simple, yet penetrating question, and it was clear just how insufficient, ridiculous and craven each one of Ford’s stammering responses were. Right there, in vivid contrast, there was what we were seeing and what we were hearing, and it simply could not have been clearer that the emperor had no clothes.

Ford didn’t come across as fun, unpredictable or larger than life, just dim, even small, like the guy trying unsuccessfully to join a conversation at the bar. Ford needs attention and desperately wants the seal of American celebrity, to step out of parochial Toronto and live amongst giants, but his aspiration is damned. He’s the kid who will never be accepted, and that hunger of his will always circle back to anger and self-annihilation. The man, dense and frustrated, is a charisma free zone, and there’s no better place than Hollywood to make something like that abundantly and mercilessly clear.