The Singing Cowboy

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Lanai, Hawaii

The missionaries left the cattle scene in Lānaʹi many years ago but the cowboy or paniolo culture remains strong in Lānaʹi – yet another quirk that makes this island special.

My mother and I arrived at Lānaʹi Western Adventures for a tour but after we signed the we won’t sue you if we die forms I heard this guy singing and it was so good I thought it was the radio.


It was Jesse the Singing Cowboy.


Originally from Arlington Jesse Taylor was basically going into bars asking if people wanted to hear songs so he could sell his CDs. In Montana a woman approached him about singing and working in Hawaii. It turns out it was the wife of the manager of Koele Stables and later on her husband offered him the job as a wrangler.

He’s definitely talented and I’m surprised no one has scooped him up yet – especially the giggling Japanese girls who were also listening along with me.

You can find out more about The Singing Cowboy on his website.



Disclosure: I was a guest of the Lānaʹi Visitors Bureau, they did not request that I write a favourable review or contemplate starting a new category for cowboy crushes.


Join the Conversation

  1. Chrystal McKay says:

    I’m on board with the cowboy crushes! Hello Jesse! haha

  2. kara rane says:

    yes.. lots of cowboys out there —>> <<— seen his a** many a New York day 🙂

  3. Camels & Chocolate says:

    If you want cowboy crushes, come visit me in Tennessee!

  4. Stephanie - The Travel Chica says:

    I’m not a fan of country music, but singing cowboys are nice to look at 🙂

    1. Ayngelina Author says:

      I’m not a fan either but I may be a fan of cowboys…

  5. Cowboy Curtis says:

    Yodeling is completely out of the picture.

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