Hugh Prestwood, Kathy Mattea, and “The Song Remembers When”

A conscientious YouTuber has uploaded many episodes of Live From the Bluebird Cafe, most of them dating from the late nineties.

When I saw one of them featured both Hugh Prestwood and Kathy Mattea, I was immediately intrigued.  Prestwood had written Mattea’s single, “Asking Us to Dance,” and she was the original artist to put a hold on “The Song Remembers When,” an eventual smash for Trisha Yearwood.

Hearing that story from both perspectives was very revealing. I won’t spoil it all here, but I will share the video.  Should it not load from the start point, skip ahead to the 37 minute mark – or just watch the whole thing, because Prestwood, Mattea, and fellow guest Cheryl Wheeler are all amazing talents.


  1. Really enjoyed the video. Thanks. Kathy Mattea was part of the first show I ever saw at the Bluebird in Jan ’07. She appeared with Suzy Bogguss, Jon Vezner and Pat Donohue.

    I never knew that “The Song Remembers When” was first offered to Kathy Mattea. It’s my favorite Hugh Prestwood song followed by “Ghost in This House”, “On the Verge”, “Asking Us to Dance”, “Hard Rock Bottom of Your Heart” and “Moon Is Still Over Her Shoulder”. Prestwood and Cheryl Wheeler have something in common. All or almost all of their songs are solo writing efforts. Cheryl is best known for writing “Aces” for Suzy Bogguss.

  2. Thanks for sharing! Not only is this one of my favorite Trisha Yearwood songs, it’s one of my favorite songs of all time, period. I still get chills every time I hear it. I also never knew that Kathy Mattea was the first one to have it on hold. I’m sure she would’ve done a great job with it, too. I absolutely love “Asking Us To Dance,” as well.

    I have to agree that Hugh Prestwood is such an amazing talent. He wrote many of my other favorite country songs from the 90’s. I also love all of the songs Bob mentioned, especially “Hard Rock Bottom Of Your Heart” and “On The Verge.” Some of his lesser known songs that I love are “Smoke In Her Eyes” and “Is That You” both recorded by Ty England, “Darlin’ That’s What Your Love Does” by Don Williams, “Latter Day Cowboy” by Collin Raye, and “Half The Moon” recorded by both Tanya Tucker and Stephanie Bentley.

  3. Jamie – yes, that’s definitely one of Crystal’s best songs. I read where the song is based on Prestwood’s marriage ending. He said that neither one was saying it but it sounded like ‘goodbye’. He wrote the idea down that it ‘sounded like goodbye’ and then wrote the song.

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