Singing about the Windy City

North Wind song by Charlie Louvin Jim and Jesse

The girls have been singing the old Osborne Brothers’ song “Windy City.” I’ve always like the song but have fallen in love with the sweet harmony the girls showcase on the lyrics.

The girls learned the song from Alison Krauss.

When the song was first released by The Osborne Brothers I was two years old. I love that the girls are still singing “Windy City,” keeping it alive for at least another generation.


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  • Reply
    Don Byers
    September 13, 2021 at 7:18 am

    And what a great job the girls did on this song…nothing beats family harmony. I remember the first time heard them…they sang at Old Brasstown Church…..long time ago!!!!

  • Reply
    Betty Brantley
    September 12, 2021 at 8:30 pm

    Absolutley Beautiful!

  • Reply
    September 12, 2021 at 7:05 pm

    Oh, well done!

  • Reply
    Don Byers
    September 12, 2021 at 5:30 pm

    Audie did write both songs I mentioned. His best friend and manager, Scotty Turner did the melodies. I knew Scotty in Nashville. He took me up to the top of the UA tower and showed me some of Audie’ s army gear.

  • Reply
    Don Byers
    September 12, 2021 at 5:23 pm

    Mel Tillis did “When the Wind Blows in Chicago”. believe it was written by Audie Murphy. I believe Audie also wrote “Shutters and Boards”. A big cross-over hit.

  • Reply
    September 12, 2021 at 12:53 pm

    Good job young ladies!!!

  • Reply
    September 12, 2021 at 9:23 am

    I so enjoyed the singing this morning!!! I watched it on utube and saw that they had another song not sure it was called this “Angels Rock Me,” but they did a great job on it too. They just get better and better. I have always loved Alison Krause’s voice. Particularly, one song she did “Star of Bethlehem,” and “Seven Spanish Angels.”

  • Reply
    Jim Casada
    September 12, 2021 at 9:10 am

    Every time I listen to to this song it gives me chills because it brings to mind thoughts of a terrible family tragedy. An aunt of mine, a beautiful woman who the first member of the family to earn a college degree, married and began a family while working in Chicago. When her child was just an infant her husband was killed in a plane crash, leaving Aunt Jessie a widow and sort of trapped in a place far from her childhood home in the Smokies.

    To her great credit she hung on, led a good and meaningful life, raised my cousin who has remained in the area, and was through all the years I remember her one of the sweetest, yet deep down one of the seemingly saddest of souls. Every summer, while on annual vacation from her job, she and her daughter would return to Bryson City for a couple of weeks. It was clear to me, even as a boy, that the high country still held a corner of her soul.

    A few years back I was privileged (and I use that word meaning exactly that–it was a singular privilege) to join her daughter, her daughter’s husband, their two children, and a few others connected to the Casada family for an early spring hike back to the place, more than a mile from the nearest trail deep within the Great Smoky Mountains National Park, to visit the old homeplace where Aunt Jessie had grown up.

    As we sat around the old spring which served the site long ago and ate a simple lunch of sandwiches, we reminisced about Aunt Jessie and what life must have been like for her and her siblings as a girl living in that remote, rugged spot. Then, in something about as deeply moving as anything I’ll likely ever witness, my cousin reached into her day pack, pulled out a small container holding Aunt Jessie’s cremains, and scattered them around an early blooming bloodroot Br’er Don had spotted. She then offered some powerful, poignant words about her mother having come full circle.

    At that point the already gloomy skies opened up, and in the way I look at it they were weeping for the wonderful woman from the high country who had spent her adult years in the “Windy City” but now was once more in the comforting bosom of the mountains. I think of her and clear my tear ducts a bit every time I hear this song.

    • Reply
      September 12, 2021 at 12:21 pm

      Just beautiful! I could almost feel the peace wash over as Aunt J was laid to eternal rest.

    • Reply
      Carolyn B Healy
      September 13, 2021 at 8:00 pm

      Well hi all! This is Carolyn, Jim’s cousin from Chicago, who is eternally grateful for the day he mentions when he and Don led my family up to the homeplace. I’m so glad he chose to share my mother’s story. She did what she could to emphasize my heritage from far away, taking me to the forest preserve often, acquainting me with May apples, Jack-in-the-pulpits, rhododendrons, and I’m sure others I’ve forgotten. And because of those annual visits to Bryson City, I got a powerful dose of Casada love and storytelling that helped me know that part of who I am, then and now. I ended up a grief counselor, so I’ve put plenty of attention to our shared history of loss that Jim so eloquently described.
      Also, you all may have turned me into a newbie bluegrass fan now!

  • Reply
    Margie G for don’t go to Shy town
    September 12, 2021 at 8:36 am

    Makes me ALMOST want to go there…. thank goodness there’s no Shytown for me anytime soon! The Pressley girls are in excellent form per usual!!!!

  • Reply
    Carol Roy
    September 12, 2021 at 8:26 am

    Very good girls… just keep getting better and better!

  • Reply
    Dennis M Morgan
    September 12, 2021 at 8:17 am

    I enjoyed listening to the girls sing the song. Their voices do blend together well.

  • Reply
    September 12, 2021 at 8:04 am

    Your girls did a beautiful job. They are so talented. I love how they are carrying on the legacy of so many wonderful songs. You just don’t see that love for heritage in young people any more. They are a blessing, as are you. Thank you, Tipper!

  • Reply
    September 12, 2021 at 8:04 am

    That is truly beautiful. It reminds of when so many West Virginians left the dying coal fields to find work in far off cities. I had family and friends to leave in droves to find work, as did I. Many made their homes in the more prosperous cities, but others came back. The “Windy City” of Chicago seemed to be a place that claimed some for life. I wonder if they missed the snow covered mountains, and longed to sit once again at their Mother’s table. I surely did, and it brought me back home. I see people from long ago that come back for funerals and such. It was a sad time for separation of families with many leaving wives and children behind. Our yearly reunion is represented by many states all across the nation, even the great state of Texas. The girls did a fantastic job on those haunting lyrics. and in the not so distant past I’m certain that song caused some homesickness.

  • Reply
    Miss Cindy
    September 12, 2021 at 7:28 am

    Your right Tip, their harmony is beautiful! Good job!

  • Reply
    Larry Paul Eddings
    September 12, 2021 at 6:53 am

    Alison Krause is absolutely one of my favorite singers. The Pressley girls sing and play so very well together. It’s always a pleasure to hear them.

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