I think the helmet Messier wears (and Buchburger and McCarthy too I think) is the worst. Looks like someone took an industrial molding from some other type of product, put foam inside it and called it a hockey helmet.
The 80's / mid-90's Jofa "Alien Skull" helmet gets honorable mention. Selanne still wears a Jofa helmet, but it's the newer one that doesn't look as retarded (pretty sure anyway).
Butch's hemet was a "lucky helmet". He'd had it since he was a kid. It was basically useless as a means of protecton. L.A. announcers used to joke about how it was really nothing but layers of paint holding together pieces of plastic. You gotta love a guy with that kind of commitment, even if it is only to a piece of equipment.
I have some old crappy Jofa helmet from 10 years ago that is all beat up and the screws pop out and stuff, it's pretty funny actually. I wear it when I play goalie in street hockey now, except there's a throat protector on it, and I put duct tape on the straps and screws to make sure it doesn't just fall apart on my head like it has in the past.:p