Roy Gentry


roy1This is a portrait of Roy Gentry. I met him a couple of weeks ago. My wife and I were walking down the street in Madison, Indiana. I looked inside a café window. I grabbed Norene and told her, “I have to paint that man!”


I went inside and talked to one of the most interesting and charming human beings I’ve ever met. He is a music historian. He is a great musician. I painted this portrait to hang in a special show about him.


Appalachian Mystic – A Celebration of Musician Roy Gentry

March 12 – April 10

Joeyg’s Restaurant & Nightclub

218 East Main Street

Madison, Indiana


The show includes music, photography, and paintings celebrating Roy Gentry’s life, which coincides with the debut of his new CD release, “Angel Land.”


I hope you like the portrait.

Comments on Roy Gentry Leave a Comment

March 5, 2009

A. Josie: @ 10:37 pm #

I like Roy Gentry and would really like to meet him. He looks like a real gem!
Love your painting.


March 6, 2009

Christine Roach @ 12:25 am #

I love the painting, and I like the story even more.

Sarah @ 7:54 am #

I love this portrait. You have captured a personality in his face.

Susie @ 11:21 am #

You have captured a personality on canvas that anyone would love to meet! Wonderful job!!

March 8, 2009

Margaret @ 1:21 pm #

Tom, I think you have done an incredible portrait! What a fascinating model you found. You’ve captured his personality for sure!He is somebody we’d all enjoy meeting.

March 9, 2009

Jennifer @ 10:34 am #

I love the portrait. What a fun subject to paint, and his story makes the painting even more interesting. I think that a painting should tell a story and this one really does!

March 16, 2009

Elaine @ 6:45 am #

I think this is one of my favorite portraits of yours. Very nice.

May 4, 2014

Lydia @ 11:52 am #

Roy is really big in the Grateful Dead community. I recently partied with him on Derby Day. We gambled together!!

April 19, 2017

Dave Siler @ 3:08 am #

I knew Roy at the Oval Door Coffee House in Louisville in the very early 70′s. Hope you’re still playing music, Roy. I know I am. Peace

July 20, 2017

A friend @ 4:35 pm #

We lost Roy to a stroke yesterday afternoon. RIP.

David Trabue @ 11:11 pm #

I just heard (I’m out on the West Coast & no longer in Louisville) that Roy passed away.

RIP, Roy!

Roy began my teen age education on Martin guitars at the Oval Door in the ’60s: Me asking a slightly older bluegrass/old timey musician, “Why do the Gibsons & Guilds have those little plastic things on the headstock & Martin doesn’t?”, He sagely said, “The Gibsons & Guilds have neck adjusting bolts under those plastic thingies; Martin don’t! Martin builds necks right so they stay right & don’t need messin’ with!” Words I’ve lived by all my guitar playing life since then…

Roy Gentry is the friend and musician who began my education on Martin guitars, Gibson mandolins & banjos, and Dobros back in the mid-60s in Louisville. I found out that he died from a stroke a couple days ago.

A genuine character, multi-instrumentalist, singer/songwriter and fixture of the Louisville, Southern Indiana bluegrass/old timey music scene… original partner/owner of the Doo-Wop music store in Louisville… leader of the Falls City Ramblers and many other bands over the decades… He will be missed by many, many people.

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