Imagining the Modern Day Highwaymen

I was recently listening to the excellent Highwaymen song “Silver Stallion,” and it got me thinking. What would a modern day version of The Highwaymen look like? The Highwaymen were the best super-group to ever come together in music history, in any genre, as far as I’m concerned. The group consisted of Johnny Cash (a true American icon), Willie Nelson (the ultimate troubadour), Kris Kristofferson (the greatest songwriter to ever live), and Waylon Jennings (tied with George Jones and Hank Sr. as the greatest country artists to ever live, in my opinion). These four artists helped shape not only the country genre but music as a whole.

Filling The Highwaymen’s boots would be no small task, but there are several giants of country music who could carry on their tradition. I did have to set some parameters. Only mainstream artists could be considered; Jennings, Cash, Nelson, and Kristofferson were all well-known throughout country music and the country while doing things their own way. What made The Highwaymen so special was the fact that all four men were established stars but successfully came together to make great music. Modern underground country artists like Whitey Morgan or Cody Jinks are carrying on the spirit of outlaw country but are unfortunately not well-known enough to be considered. Secondly, the artists I am considering still have to be performing today. Randy Travis would be a great choice for inclusion, but his recent health problems have sadly taken him off the stage. Third, the artists must be older veterans of the genre. Artists like Eric Church and Jamey Johnson will one day reach that status, but they’re not quite there yet. So with those disclaimers out of the way, let’s take a look at who made the cut.

Clint Black, Tracy Lawrence, and Mark Chesnutt were all given thought. All three are great artists, but their impact on country music throughout their careers has just not been big enough. Similarly, John Anderson would bring a uniqueness to a modern day incarnation of The Highwaymen. He’s got one of the most distinguishable voices in country music and recorded two of my personal favorite songs, “Seminole Wind” and “Straight Tequila Night.” Again, however, his career hasn’t had a big enough impact on a large enough scale to be included. I also wanted to include Gary Allan and Brad Paisley but did not for two different reasons. Gary Allan’s outlaw attitude toward the genre and his approach to country music is badass, but after Set You Free and a couple of hit singles, Allan has gone quiet due to some problems with getting a new album released. Brad Paisley, on the other hand, is still an established superstar in the genre, and his career has not yet been quite long enough to warrant inclusion, but he’ll be there quite soon. Finally, Travis Tritt was right on the verge of ending up in the final four artists. He’s a modern day outlaw and makes sure the spirit of Waylon survives. He almost made it.

Yet the modern day version of The Highwaymen came down to George Strait, Alan Jackson, Dwight Yoakam, and Vince Gill. If you split the history of country music right down the middle and look at the genre pre and post-1980, Strait, Jackson, Yoakam, and Gill are arguably the four greatest country artists of the post-1980 generation. Each warrants inclusion in a modern day incarnation of The Highwaymen for several different reasons.

A Country Music Hall of Fame member, Vince Gill is the definition of Nashville. He’s everywhere. He recently celebrated 25 years with the Grand Ole Opry and will sing with pretty much everyone. His guitar playing is incredible, and he’s racked up 20 Grammy’s and 18 CMA’s. Most importantly, people rave about Vince Gill as a man. In every interview I’ve ever watched about Vince, artists consistently thank him for the help he’s given hundreds of artists. Oh, and he’s pretty much connected to every artist in music somehow. Check this out.

George Strait, a fellow Country Music Hall of Famer, has been coined the “King of Country Music.” Along with Randy Travis, he helped usher in a new generation of country traditionalists in the 1980s. Most remarkable about George Strait is his consistency. For over thirty years, Strait released classic after classic, never straying from his tried and true formula of mixing western swing and neotraditionalism. He survived many shifts of the genre by just recording what people expected of him. Strait would admirably carry on the tradition of Willie Nelson’s troubadour-like performances.

Along with George Strait, his sometimes duet partner, Alan Jackson was a shoe-in for inclusion. Jackson writes songs in the vein of early-Haggard- working man anthems and odes to country living. He was and still is a prolific songwriter; many of his 34 number one singles were written by his own hand. Jackson is truly as traditional as an artist can get. A listener knows exactly what he or she is getting with an Alan Jackson album- straight, traditional, hard-country.

Dwight Yoakam brings a celebrity factor to a modern day version of The Highwaymen. Like Nelson and Kristofferson, Yoakam ventured out to Hollywood and acted in several movies. He’s also one of the “coolest” country artists to ever live. He was influential in bringing back the Bakersfield sound to country radio, and his debut album Guitars, Cadillacs, Etc., Etc. is a classic of the genre.

But The Highwaymen were not successful just because all four artists were stars and could count many accomplishments among the four. The Highwaymen were special because Jennings, Cash, Nelson, and Kristofferson each were able to perform and record together without losing their signature sounds and styles. Watch any performance from The Highwaymen, and it looks like they’ve been playing together their entire lives. The four artists chosen here- Jackson, Strait, Yoakam, and Gill- are talented enough to perform together and keep their own sounds but play together in a cohesive fashion. Imagine Yoakam and Gill playing Bakersfield style on one stage. Think about Jackson and Strait playing hit after hit and swapping lines. It would be magic each time the four artists stepped on stage together.

So what would a typical set list look like? This was the toughest part of writing this article but also the most fun. I put the show at thirty songs. enough for each artist to get seven of their songs plus two covers:

Guitars, Cadillacs
Chasin’ That Neon Rainbow
Honky Tonk Man
Unwound
High Lonesome Sound
Tryin’ To Get Over You
Buenas Noches From a Lonely Room
The Fireman
Write This Down
Small Town Southern Man
Gone Country
Next Big Thing
Oklahoma Borderline
Amarillo By Morning
The Talkin’ Song Repair Blues
A Thousand Miles From Nowhere
Don’t Rock the Jukebox
Fast as You
Ocean Front Property
Down to My Last Bad Habit
Streets of Bakersfield
When I Call Your Name
I Can Still Make Cheyenne
Good Time

Encore
One More Last Chance
The Race is On (George Jones Cover)
She’s Got the Rhythm (I Got the Blues)
Turn It On, Turn It Up, Turn Me Loose
Highwayman
Troubadour

So there it is. The modern day version of The Highwaymen. Leaving some songs off the set list was incredibly difficult, particularly with George Strait’s catalog. Imagining Alan Jackson, George Strait, Dwight Yoakam, and Vince Gill all on stage together and touring the world is a country music fan’s dream.