I have ridden as a courier in Toronto. For me, it was the 80s, and IIRC, I rode for Sunwheel Couriers, who had an old-school (even by the standards of the 80s)

I have ridden as a courier in Toronto. For me, it was the 80s, and IIRC, I rode for Sunwheel Couriers, who had an old-school (even by the standards of the 80s) touring/randonneur culture. I was riding a bike very similar to what you describe: Flip-flop hub from a BMX bike with a fixed gear on one side and a freewheel on the other. Frame was an old CCM that weighed a ton. What can I say, I idolized Nelson Vails! The owners admonished me to get a bike with gears before I destroyed my knees. I did not listen, and perhaps that—or twenty years of Ultimate, or twenty-five years of rock climbing—did them in for me. When I was riding most of the couriers I met were chain-smokers, often cruising the streets with a cigarette hanging from their mouths. Very insular counter-culture, very opinionated about bikes. And in my limited experience, very little overlap with the rest of cycling culture.