VIDEO: A look back at the day a celebrity tried out for the Leafs.

It takes a very unique skill set to play hockey at any level, the skating alone is rather difficult for some people to get used to. That's why it was no surprise that when Conan O'Brien skated with the Toronto Maple Leafs back in 2004 he looked like a fish out of water. Literally evvery aspect of his game was horrendous, from the shooting, to the skating, to even just basic balance on his feet looked terribly awkward. To be fair as a comedian he may have been playing it up for the camera a little, one has to wonder though, with the Leafs recent struggles could we one day see Conan O'Brien back for another try-out?