The Story Behind My Recording of Hugh Prestwood’s Song When I Died

In multiple decades of writing songs and recording albums, I’ve only recorded one song that I didn’t write myself: When I Died, written by an old friend of mine, hit Nashville songwriter Hugh Prestwood. When I heard that Hugh had passed away in late September, I decided it would be a fitting tribute  to tell the story of our friendship and how I came to be the only artist — as far as I know — to record this song.

I moved to New York City in my early 20s, hoping to find fame and fortune in the music business. At first I sang in hole-in-the-wall clubs and a few bars, performing for small audiences who largely didn’t care about me or my songs. I figured this was part of “paying my dues.”

One night I went onstage in a small club to find that there was only one person in the audience. Nevertheless, I cheerfully sang my set, and then took a seat.

Then he got up on stage and sang his set.

The irony of the situation wasn’t lost on either of us, but we both figured it would make a good story someday. (Ha!) Meanwhile, I was impressed by this guy’s songs, and he liked mine as well, so we struck up a friendship. If you haven’t already guessed, the young singer-songwriter I’d just met was Hugh Prestwood, who would later go on to write many country hits and end up in the Nashville Songwriters Hall of Fame.

The two of us, joined by our friend singer-songwriter Maureen McElheron, eventually became a sort of informal songwriter’s roundtable. (Maureen would later go on to success creating music for the films of animator Bill Plympton, two of which have been nominated for Academy Awards.) The three of us would try out our latest songs on each other, which was fun, inspirational and sometimes educational. For example, I recall that I hadn’t given much thought to rhythm and tempo when creating my earliest songs, but when I heard Hugh’s demos, the rhythms jumped out at me. That was a wake-up call, and I started paying more attention to that aspect of my songwriting. Meanwhile, we sometimes joined each other on stage at “open mic” nights, where we sang harmony on each other’s songs.

I thought all of Hugh’s songs were terrific, but one song, titled When I Died, really jumped out at me. It told the story of a young man’s experiences after dying, and I saw that it left audiences stunned. So I decided to learn the song and add it to my own repertoire — the only song in my shows that I hadn’t written myself.

Hugh, who didn’t have a powerful voice or a lot of stage presence, was determined to succeed as a songwriter, and over the years his dogged determination paid off. He started spending time in Nashville, and after years of knocking on doors, his songs started to get recorded. Soon, he was having hits, culminating with winning BMI’s Country Song of the Year award in 1991 for Hard Rock Bottom of Your Heart. In 2006 he was inducted into the Nashville Songwriters Hall of Fame.

By the early 1990s I was working on my second album, Doorway, and I wanted to record When I Died for the album. Hugh happily gave me permission to record it, noting that no one in Nashville was interested in the song — it was too unusual! (A special note of thanks to the people who worked with me to create the recording: producer Bill Kollar and musicians Janice Hardgrove Kollar, Jay Azzolina, Vic Colucci and Marshall Rosenberg.)

It’s fitting that the person who told me about Hugh’s passing on September 22 of this year was the third member of our little songwriter’s roundtable, Maureen McElheron. My first thought upon hearing the news was that I should post When I Died, first released 30 years ago, on my website as a tribute to Hugh and his legacy of beautifully crafted songs.

Hugh, thanks for your early inspiration and friendship. Safe travels in your next adventures, wherever they may take you!