I had the honor of staying in East Saint Louis a couple of times
I remember walking to the liquor store and saw a group(about 7-8) of hookers (all around 14-17) walking threw alleys and looking for cusomers. When I finally got to the store it was about 4 drunks of the corner, a crackhead In the middle of the stree and another group of people across the street. Around the corner is a block of old dirty houses that had people sitting on the porch and barking at anything that walks by. smh
Where you lost? What were you doing in the hood? Every city has parts of town just like that. If you have no business in the hood then dont go.
The worst city I've ever been to is Allegan, Michigan. I used to date someone who lived in Holland, MI (along the coast of Lake Michigan) and Allegan just happened to be the halfway point between my home and Holland. As such, I was driving past Allegan all the time, and the city itself sits on a beautiful riverfront. There's a boardwalk, fountain, classy looking, small-time buildings. It appeared to have a certain charm about it.
So, one day, my girl and I decided to meet in Allegan for once. It was mid-afternoon on a weekday. The city was nearly vacant. Every other store was an antique shop and absolutely nothing was open. A tumbleweed truly and carefully whisped its way across the street. Two eateries remained open: a saloon and Pizza Hut, so we tried the saloon. We took two steps in, saw one man at the bar in a cowboy had and boots, then took two reverse steps right back out.
Out of options, we settled on Pizza Hut and spent the rest of the night selecting our favorite LFO and Billy Joel songs from their jukebox. Allegan is the most dissapointing city of all-time. Also, it's the meth capital of Michigan. So I guess a city can only dissapoint you so much with a moniker like that.
I'm not sure about worst city... but the worst areas I've ever found myself in were East Oakland and Puerta Vallarta.
I had a friend who went to a music school in Oakland, and the area he lived in was straight up scary. When I wanted to go to the store, I actually drove about 15 minutes to another area, because I didn't want to get out of my car at the local spots.
In Puerta Vallarta I took a cab with a one-armed Mexican to the ghettos to hook up some coke (talk about drunk and stupid). We drove about 10 minutes into the city, and I would simply describe the area as 3rd world. People living in concrete holes in the wall, and streets that looked like a warzone.