I've met him a few times, but the first time was the best:
In the summer of '03 I was flying back from the West Coast and missed my flight to Calgary. I had to take a flight to Edmonton instead with a three hour layover there. The reason I missed my flight was that I had lost a big toenail playing soccer that day and was limping around like crazy. (Among other things like ferry schedules.)
Iggy came up to me during the layover and asked what was wrong with my foot while we waited for the same flight. The terminal was deserted, so we just shot the sh** for three hours. Best part was me complaining about how crappy the Flames were. The guy is just super optimistic and said he had a "feeling" about that year and praised Darryl Sutter. Myself, being the jaded Flames fan, called bullcrap that they'd be any good.
We made a bet. He won. Never collected, although I don't think we actually bet anything. A very fond memory of mine.