Running on the south side of chicago for four years (as a member of the university of chicago cross country team) gives you plenty of stories. Here are a few highlights:
1. While running through a particularly sketchy area, a car drove past us and a dude leaned out the window with a paintball gun spraying at us. One of our teammates got hit in the eye, had to go to the hospital.
2. One of my teammates forgot to look both ways and got hit by a car going about 25mph; he rolled up on the windshield and into the air as the car kept driving just like in the movies. The car drove away but some locals saw and called the cops right away so the driver came back. The kid went to the hospital but ended up running 8 miles the next day; I think he was lucky to not break a leg, let alone survive.
3. The team ran past a particularly talkative homeless man who gave us this suggestion: "y'all should get a woman on the team, so when you're done running, you could f*ck her"
4. While running in a thunderstorm, instead of running on the sidewalk on this one street like we usually do, we ran in the road. All of a sudden we heard a really loud bang and saw an explosion - lightning struck a transformer on a telephone pole only about 10 yards away from us, and a electric wire whipped down to the sidewalk. Lucky break.
5. Another car rage story: the guy I was running with slapped the back of a car stopped in the crosswalk, and a big black dude got out, yelling at us. We kept running but he hopped back in his car and drove after us. My friend was unfazed but I was terrified and sprinted off. So the dude thought I did it, and drove after me - he was getting close to me and I was afraid he had a gun, but I took a couple turns going the wrong way down one way streets and he stopped following me.
We also ran past a ton of drug deals but none that were particularly interesting. Basically every run on the south side was a crazy run in some fashion.