In chronological order:
1. Lori-Ann Muenzer winning the women's sprint in Athens 2004. Nobody gave her a real chance, Cycling Canada wasn't interested in supporting her at all, yet she became the only Canadian to ever win Olympic gold in cycling. Her semi-finals win against Anna Meares was just incredibly gritty.
2. Eric Lamaze winning individual show jumping gold in Beijing 2008. The entire show jumping competition was a dream for Canada in 2008, with long time Olympian and Canadian show jumping legend Ian Miller picking up his first medal. But it's Lamaze's gold medal that was the most amazing. The drama of the jump-off for gold (following a very long and very entertaining bronze medal jump-off) was incredibly compelling. But most impressive is the amazing redemption story for Lamaze, who's life was derailed by cocaine addiction. Cocaine also robbed him of his chance to compete in the 1996 Olympics.
Unfortunately there has been tragedy since, with his beloved horse Hickstead dying in the ring a few years later, and recently Lamaze has sadly been battling brain cancer, and we all wish him the best. But that one night in Beijing was a perfect fairy-tale ending.
3. Penny Oleksiak winning gold in the 100m freestyle in Rio 2016. I almost don't feel like I have to explain that one. First gold medal for Canada in swimming or track and field (the two biggest Olympic sports) that I could remember, won by a young athlete that came out of nowhere in a huge come from behind victory. The tie with Manuel, who also made history in a bunch of ways, was pretty cool, too.
Bonus: Tiësto's awesome trance set at the 2004 Olympics.