I sat accross from Don Cherry and Ron McLean on a flight YHZ-YYZ. I was continuing on to YGK and made sure I got Don (and Ron) to sign my Kingston boarding pass!
In terms of a previous post, I see Dan Ackroyd in Kingston once in a while(He lives in the area), he drives a blacked out Ford Excursion, usually driving with his windows down, rock and roll blaring. Super nice guy, we always wave at him, he usually waves back.
And finally, the greatest sighting I have had, in the Empress lounge in T3 a few years ago: Heidi Klum. I approached her, and completely froze up when she looked up at me. Absolutely goregous, and very friendly. Signed an autograph for me (used her gold pen!), said "here you go cutie" and proceeded to move into a more remote corner of the lounge, with the large man she was travelling with, presumably to avoid more gawkers like me.