Kentucky Derby Songs

John Prine, Billy Strings, Elvis, and My Old Kentucky Home

“Kentucky Derby races, my presence in the spot is so abrasive

Box at the Churchill downs, that's motivation”

-Jack Harlow’s “Churchill Downs” (feat. Drake)

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Adam Tait, our “Eclectic Corner” friend, assured us that this lyric from the Louisville native’s song was the perfect start to this week’s Derby edition of the Swap.

We’re going with it! And we’re letting Adam be the bugler and call the songs to post this week:

Riders up! As Oaks is upon us and the Run for the Roses grows nearer, it’s time to take a trot a bit longer than the one and one quarter-mile lap around Churchill Downs. Come with us as we hear from Kentucky’s favorite son, the Secretariat of songwriting, John Prine. We’ll also listen to the King and the bluegrass sensation, Billy Strings.

Our final stretch (Bonus Track) is perfectly fitting - a tribute to every Derby beginning, “My Old Kentucky Home.”

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Paradise by John Prine (Kody)

I once heard Prine open and close with this song at a show in Louisville. It’s a classic and one that anyone from Kentucky should know. Who could possibly write a song that makes you feel so at home while drawing your attention to the negative impact of strip mining for coal on communities like Paradise, KY? Only Handsome Johnny.

Handsome Johnny, now that’s a great name for a Derby thoroughbred.

Also available on Apple Music.

Watch It Fall by Billy Strings (Ben)

I pick my Derby winners by name. Had a friend stop me a couple years ago - he was shocked I had not heard of Billy Strings - the virtuoso, the prodigy, the breakneck strings picker. He’s generated these headlines and more from top music critics. If you dip into bluegrass every once in a while, you’ll enjoy. Watch It Fall is one of my faves, it has a little more blue than grass. (Start with Dust in a Baggie if you want a grassy toe-tappin start). If “Billy Strings” was racing Sat, I’d place an exacta bet on him and the favorite.

Also available on Apple Music.

Kentucky Rain by Elvis (Jonathan)

Saturday will be the 18th Kentucky Derby since I have lived in the Bluegrass State, and I’ve had the opportunity to attend “The Most Exciting Two Minutes in Sports” twice when I lived in Louisville. It was truly thrilling to experience those two minutes (albeit I could hardly see the horses from my spot in the infield!). The first Saturday in May in Kentucky can be absolutely beautiful with the sun shining down on all the race goers in their finest seersucker attire, or everyone just as easily could leave with their hats soaked from May showers. There have been many songs written about Kentucky, but Elvis’ recording of Kentucky Rain makes me think of the Derby and the absolute muddy mess it was one year when I attended. This year the weather outlook is perfect with no cold Kentucky rain pouring down.

Also available on Apple Music.

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Bonus Track: A Tribute to My Old Kentucky Home by Colby Adams

As a son of the Bluegrass State, there are few days in the year that mean as much as the first Saturday in May. While the Kentucky Derby draws attention from around the world, the state of Kentucky comes to a standstill for those electric two minutes. But it is the moments preceding the horses being led into the starting gate that I want to talk about today. It is my favorite part of the Kentucky Derby—the playing of “My Old Kentucky Home” as the horses are led onto the track at Churchill Downs.

“My Old Kentucky Home,” originally composed as an anti-slavery song by Stephen Foster, has a complicated history. By 1986, the song’s original meaning had been overshadowed by the use of a racial slur, and the song was revised to the version we hear today.

As a Kentuckian, however, this song echoes in the background of some of my most treasured moments. I remember the pre-game festivities when I first attended a Kentucky basketball game at Rupp Arena as the crowd in unison held up the number one while singing “I will sing one song for my Old Kentucky Home.” I remember the first time I watched the Kentucky Derby after moving away from Kentucky and feeling a deep sense of pride swell up inside me as the camera panned the crowd at Churchill Downs as they were singing the line, “weep no more, my lady.” 

The song itself is not the anthem that other state or national songs are. It does not hype up the crowd like other pre-game music. It is a somber song that was originally written as a song of lament. It deals honestly with the struggles of life. But it is a song rooted in faith and hope, even if that hope is only realized in eternity. Because of all of this, it is a song that perfectly captures my beloved Bluegrass State. 

If you have the opportunity this Saturday to watch “The Most Exciting Two Minutes in Sports,” go ahead and tune in a few minutes early to take in the playing of “My Old Kentucky Home.” While it may mean more to those who call Kentucky home, it is a song to which all of us can relate. In the meantime, enjoy several of my favorite renditions of this great song linked below. 

1. My Old Kentucky Home, Goodnight by John Prine

2. My Old Kentucky Home by Acoustikats

3. My Old Kentucky Home by Loretta Lynn

4. Old Kentucky Home by Louis Armstrong

Colby Adams is a native Kentuckian living in Fort Worth, Texas. He loves the Yankees. His bucket list concert is Bruce Springsteen and his most played artist so far in 2023 is probably Taylor Swift. (Gotta get ready for the Eras Tour)

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Thank you for reading The Music Swap. What are your favorite songs about Kentucky? Drop a reply in the comments or respond to our email.

-TheMusicSwap