I don't consider the people who own the car to affect the "coolness" as I'm looking at the car not the idiot driving it, in my opinion anyway. I know it does for the TopGear cool wall, but I don't give one about the owner/driver. And that applies to all cars, even if it was the Lotus 7 driven by Patrick McGoohan in The Prisoner. (though Lotus 7's are cool anyway).
I imagine everyone has someone they hate that would potentially drive every car that comes up on the cool wall. There are many unlikable people who drive many of these cars because of the very fact they are cool in the first place.
I could also say that Jeremy Clarkson also owned a Cossie once but then again maybe he's not really "cool".