61: My other high school job
When I was 16 and 17, I worked on and off pretending to buy cigarettes underage from gas stations. I didn't work with the cops, but with a private vendor called C-Chex. I would try to buy cigarettes, and they would either card me and turn me away (and pass) or complete the transaction (and fail). I also rated the bathrooms for cleanliness. We drove to ten to twenty gas stations in a day. I drank cappuccinos from the push-button machines, and I read books in the car.
I never knew what cigarettes to buy, even after trying cloves with a friend. So one stop I'd ask for American Spirits, the next for Virginia Slims. On top of that I looked 14. Anyone who sold to me deserved what they got.