Summer of '04 Trivia

Each of the seven posts in the Summer of '04 series was named after a song. Each of these songs has a connection to the city the post was about, some being more obvious than others (e.g. "Look Out Cleveland," "Detroit Rock City," "Meet Me in St. Louis, Louis").

For each song, name the artist who is best known for performing it, and for the two songs for which it's not obvious ("The Long Cut" and "The Sheltering Sky"), identify the connection between the artist and the city the post was about. Also, one of the songs ("Pittsburgh Town") was written by an artist who is more famous than the song's best known performer. So, for that one, I'm looking for both performer and composer. In all, this makes it a 10-part question.

As a reminder, here is the list of posts/songs again:

1. Look Out Cleveland
2. Cleveland Rocks
3. Detroit Rock City
4. Meet Me in St. Louis, Louis
5. The Long Cut
6. The Sheltering Sky
7. Pittsburgh Town

Of course, there's one particular reader of this blog who's the clear cut favorite to be the first to answer the question correctly. I'm certainly not discouraging him from proving me right, but I look forward to seeing if anyone else has what it takes to beat him to the punch.