To me the Ole chant has always been a ''we're having a good time'' chant. Whenever the game is getting exciting, that's when it starts up and obviously that usually coincides with scoring goals and taking a lead. I'll always remember sometime in the mid-00s the chant starting up after an amazing 5 on 3 PK by the Habs after a suspect call from the referees so that chant does come up on other occasions. Hell, I've even heard during at the initial puck drop.
In the past few years, it has become perceived as a bragging/victory type chant by opposing fans which always seemed kind of funny when the actual bragging chant, NaNaNa Goodbye, is right there and ready to be fired off at a more opportune time.
Anywho, who cares, I'll never be against anything that adds more ambience to a game. To me, that's like asking NYR fans to stop chanting Potvin Sucks even though he hasn't played since the 80s.