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Definitly Pittsburgh and San Fran. I think Carlton St in Pittsburgh is the steepest in the U.S. Pittsburgh also has many "streets" that aren't actually drivable. They are just staircases with houses on either side and actually have street names.
Oakland has some crazy steep roads up in the hills too as I recall. And a few areas surrounding SF, like Brisbane. I almost flipped my truck over once trying to do a 3 pt turn since the steep road I was on was getting too narrow. Of course I also had my breaks start to give in my old car once near Telegraph Hill in SF b/c the street was too steep. I had to sway from side to side in reverse to get back down off that block (that was pretty scary).
And nothing's worse than driving a questionable stick and getting stuck behind a cable car going slowly uphill on Powell and California. If you don't have a strong enough clutch and e-brake, don't even consider it. And even then, its not even worth the stress.
There are super steep areas all over the Bay Area, from Marin County all the way down to Santa Cruz. But for large cities, SF and Oakland are as bad as I've seen.
There is at least two steep roads in Knoxville, Tenn. One by the newer county courthouse/jail parking garage and another one just off Gay Street between the old Knoxville News-Sentinel/Knoxville Journal building and I believe, the First Tennessee Bank mid-rise building.
Both Los Angeles and Pittsburgh have steeper streets than any in San Fran, and Canton Avenue in Pitt is arguably the steepest drivable street in the world at a 37% grade. There are entertaining videos on youtube of people attempting to drive up it in the winter. Bonus List
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