Dierks Bentley Goes Bluegrass in Telluride with New Band Long Jon

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You really have to admire Dierks Bentley, no matter what you think of his big radio singles or major label releases. You can put him in the class of one of the most successful modern country artists. And sure, he’s had to tow the line with Music Row at times to get there. But it’s unmistakable that he also takes the time to follow his heart, and do what he wants to do, even if that comes at the detriment of revenue in the long-term.

The 50th Annual Telluride Bluegrass Festival commenced on Thursday, June 15th in Colorado, and for Dierks, it might as well be in his backyard. A part-time Telluride resident, Dierks often shows up for the festivities, even if he’s not directly participating. Last year he proved just how much of a good dude he was by sticking around in the rain for the first Telluride headlining set by Molly Tuttle and her band Golden Highway. Dierks had jumped on stage with Tuttle in previous years, and recently took her out as an opener.

But this year, Dierks did more than just attend. Though he wasn’t mentioned by name anywhere on the festival posters or in the publicity copy, Dierks was there with his dedicated bluegrass band called Long Jon. In 2022, Long Jon started making appearances at the legendary Station Inn in Nashville, known for being the home of bluegrass in Music City, and where Dierks got his start in town way back in 1994. Soon a standing residency on the first Tuesday of every month started coming together.

Joining Dierks Bentley in Long Jon is:

–Guitarist and Bluegrass Director at Bethel University Ben Helson, who Dierks refers to as the true leader of the band.
–Solo performer and well-known banjo player Charlie Worsham
–Fiddle and mandolin player (and full-time Dierks Bentley touring musician) Dan Hochhalter.
–Dobro player Josh Matheny.
–Banjo player Tim Sergent.
–Dierks band bass player Cassady Feasby.
–Dierks band drummer Steve Misamore.

What or who is Long Jon named for? The real Long Jon is Dierks Bentley’s tour bus driver.

Grinning from ear to ear, Dierks said about Long Jon making their debut at the Telluride Bluegrass Festival, “It’s the greatest stage in the world, and the greatest view.” It was also Charlie Worsham’s first time playing the festival, despite playing with anyone and everyone in country and bluegrass for years.

Long Jon’s set was mostly filled with bluegrass standards, and showed extra favor to the catalog of Jimmy Martin, from “Sugar Coated Love” to “Freeborn Man.” Dierks also played a couple of selections from his recent Colorado-inspired album Gravel & Gold including “Sun Sets in Colorado” and “Still.”

Though Dierks is definitely the big name of the band, all the members took turns singing and soloing, except Bentley didn’t play any solos. He left that to the experts, and humorously blamed having the wrong pick for flatpicking as his excuse. With the level of the talent on the stage, Dierks was smart to cede attention to the other players.

At one point, fiddle player Jason Carter and Ronnie McCoury of the Del McCoury Band joined Dierks and Long Jon on stage for “Fire On The Mountain” and “Midnight Flyer.” Later members of Greensky Bluegrass and Sam Bush also joined in. Near the end, Charlie Worsham sang a version of Jimmy Martin’s “Homesick” that was absolutely divine (see full set list at bottom).

Even though Dierks Bentley might be considered a bit too mainstream for the bluegrass world, the Long Jon set was definitely appropriate and highly-appreciated by the Telluride Bluegrass faithful who had to fight through fits of mountain rain during the afternoon set.

Of course Dierks has a long history with bluegrass himself, first coming up at The Station Inn in Nashville, and releasing the album Up on the Ridge in 2010 featuring The Del McCoury Band, Alison Krauss, Chris Thile, and The Punch Brothers, all of whom are also playing the 50th Annual Telluride Bluegrass Festival this weekend.

Dierks has another side project with his band, the side-splitting 90s-inspired Hot Country Knights that just released a new single “Herassmeant.” It’s these kinds of efforts that separate him from the mainstream country herd.

But it all started with bluegrass, for Dierks Bentley, and for country music. Dierks knows that more than anyone. And even though he does his time cutting radio singles and playing arenas, he also takes the time to pay homage to the past. And with Dierks, you know it’s not just for presentation. It comes from his passion for the bluegrass art form.

All photos Kyle “Trigger” Coroneos

Charlie Worsham
Ben Helson, who Dierks Bentley calls the bandleader of Long John
Dan Hochhalter
Josh Matheny
Tim Sergent
Steve Misamore
Cassady Feasby

(Mostly complete) Set List:

Mountain Dew
John Hardy
Sugar Coated Love (Jimmy Martin)
Guitar Picking President (Jimmy Martin)
Drink Up and Go Home (Jimmy Martin)
Come Back To Me Is My Request (Billy Monroe)
Somewhere Between Me and You
All By Myself
Sunsets in Colorado (Dierks Bentley song)
Still (Dierks Bentley Song)
Fire on the Mountain (with Jason Carter & Ronnie McCoury)
Midnight Flyer (with Jason Carter & Ronnie McCoury)
Last Call for Alcohol (Ronnie McCoury)
A song with Greensky Bluegrass folks
Homesick (Jimmy Martin, sung by Charlie Worsham)
Freeborn Man (Jimmy Martin)

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