Songfacts®:

• "Pittsburgh" is a track recorded by Wilco for their 13th studio album, Cousin. While the song uses the city of Pittsburgh as its title, the lyrics don't explicitly refer to the city. Instead, they offer a series of fragmented images and ideas that create a sense of longing, introspection, and a touch of sadness.
• I've always been afraid to sing
  That's a little thing
  Somehow, that's all I do
  Strange as that seems
  I've outlived
  My dreams
  
  Frontman Jeff Tweedy told Uncut magazine that "Pittsburgh" is probably the most personal and autobiographical song on Cousin. "I hope that it's taken positively," he said. "'Out living my dreams' sounds sad. What a gift, to have all this extra life!"
  
  "My dream was to have a band, a record deal with an independent record company, and a place to go to play music," he continued. "Playing in a bull fighting arena in Spain was not something I could ever picture. The bands that I loved were in fans, going to tiny clubs and I thought they had the best life. My dreams now are for my kids, or my greatest wish is I keep doing this. If anybody asks me, what are your goals? Being allowed to do this!"
• Tweedy wrote "Pittsburgh" many years before Wilco recorded it for Cousin. "Some of my favorite songs sometimes don't find their place on a record at first," he told Uncut. "That was true of 'Pittsburgh.' That's been around for a long time."
• Cate Le Bon produced the song along with the other Cousin tracks. The Welsh singer-songwriter Cate Le Bon has also worked with Manic Street Preachers, The Chemical Brothers, John Grant and Courtney Barnett. Of working with Le Bon, Tweedy said: "Cate is very suspicious of sentiment, but she's not suspicious of human connection."