Boston. IYKYK.

Phoenix IMO, a gigantic grid where every street corner looks exactly the same due to the human tumor of suburban chain retail development. Makes you feel lost in a machine. You never know where you are, always feel lost and dependent on maps and apps to get anywhere.

Most of Houston is parking spots. Unwalkable and unbicycleable, little greenery. Gets scorching hot.

Lexington is long notorious for how the street names change despite that you're still on the same street. I will look that up though, not everyone there is insane

I can't weigh in on a lot of the cities people have mentioned. I will say the Charlottesville is impressively terrible for making it miserable to drive, bike, walk, or use public transit. You would think they would get at least one mode of transportation to be ok, but nope.

I'm putting in a vote for Pittsburgh!

Manhattan gave up south of 14th Street

Charlottesville mentioned, "the hottest thing to come out of that stinking little town" engaged:

https://lackeydie.bandcamp.com/album/s-t

Interested to understand why Lexington is bad. I've never seen it, but there was a recent CityNerd episode praising its urban design.

Merced, CA has some of the most fucked up on-ramps to the freeway I have ever seen, as well as incredibly dumb roundabouts and poorly labeled 1-way streets.

I absolutely hate driving around there. Even just going down to Fresno on 99 sucks ass once you get to Merced because the freeway is split there so you have to get off, go through city traffic, then get back on a few blocks later.