The Highwaymen, "Highwayman"

Ken dives head first into the big river

Mitch Blum

CJ Kaplan

, and

Ken Warshaw

Nov 03, 2021

Ken’s Pitch:

“Too often I would hear men boast of the miles they covered that day, rarely of what they had seen.” - Louis L’Amour

If the names Cash, Nelson, Jennings and Kristofferson don’t immediately make you think of four absolute legends of American music, let me refresh your memory. Johnny Cash is the gold standard for country music. People I know that hate everything about country music give disclaimers all the time like “Oh, well of course I like Johnny Cash. I just don’t like country music.” Before the cringe-worthy FedEx commercials, Willie Nelson was right next to Cash as one of the defining country artists of our time. At the height of his popularity in the ‘70s and ‘80s, Waylon Jennings sold out arenas and large auditoriums all over the world, and of course, GenXers will undoubtedly know him best as “The Balladeer” from The Dukes of Hazzard. If you’ve ever heard Janis Joplin’s famous cover of “Me and Bobby McGee”, you can thank Kris Kristofferson who wrote that classic. Kristofferson is also a great actor, and is responsible for the best version of the thrice-famous film A Star Is Born, where he starred and held his own right alongside the GOAT, Barbra Streisand.

The four had been friends for years (except for Cash and Nelson) when they decided to get together to make some music in 1984. What ended up being released as Jennings, Nelson, Cash, and Kristofferson (the name “The Highwaymen” was given to them later when they released their third album), is a beautiful collection of songs about reflection on their lives and longing for a time that they believe made America great.

But here’s the thing, while they haunt us with singing ghosts on “Highwayman”, awaken the spirits of Remington and George Armstrong Custer on “The Last Cowboy Song”, and lament about an oil-man friend who’s growing old and irrelevant, who Cash calls “one of the heroes of this country” on “Desperados Waiting For A Train”, they are also well aware of American imperfection.

It is not an accident or coincidence that they chose to tell their tales of their own struggles with drugs and alcohol with the corny yet sincere “Committed to Parkview”. America is, after all, a place where so many of our neighbors and loved ones have succumbed to addiction. The apex of the album is their cover of Woody Guthrie’s “Deportee (Plane Wreck at Los Gatos)”. It’s the true story of a 1948 plane crash that killed 4 American citizens and 28 Mexican migrant workers. Guthrie wrote it because he thought the treatment of the migrant workers after the crash was abhorrent. Newspapers and radio stations all over the country announced the deaths of the Americans by name and made a (justifiably so) big deal about the friends and families they left behind. The Mexican migrants were a secondary story and they were only referred to as “deportees”.

It seems strange almost 75 years later, we’re still a country that continues to “other” groups of people by dehumanizing them with words like “illegal” and “infestation” and squeezing them into the margins. What we’re failing to see as a Union, and what The Highwaymen showed us, is that you can yearn for certain aspects of the past when times were simpler, while still acknowledging that what made America great in the first place was that we know we’re deeply flawed, but we’re always trying to do better and become more inclusive and respectful of all humankind.

The song choices on Highwayman are spectacular because they’re significant. There are a few “wow” moments on the album, mostly from Marty Stuart’s guitar and Willie’s vocals, but I won’t deny the presence of schmaltz (that’s Yiddish for ‘rendered chicken fat’ but loosely translated as ‘super-cheezy’). The message however is undeniable, and I embrace it. Honesty about who we were, where we’ve been, the mistakes we’ve made, and where we want to go from here might just be the key to making America empathetic again.

Mitch’s Response:

In 1973, the five original members of The Byrds reunited after six years apart, put aside their difficult past, and created the quickly-forgotten Byrds album. Legend has it that Roger, Gene, David, Chris and Michael worked so hard to get along - and smoked so much strong weed - that there wasn’t any tension in the room. Everyone deferred to each other, no one fought, and the result was a pleasant but dull album that failed to capture the high-flying spirit of The Byrds. It turned out that what destroyed them in the first place was also what made them great.

The idea behind The Highwaymen is incredible - a super-group comprised of the creative forces that invented outlaw country (and Kris Kristofferson) who possessed the most recognizable voices in all of music (and Kris Kristofferson). Unfortunately for us, the execution of the Highwayman album doesn’t nearly live up to the promise of the concept.

From the uninspiring song selections to the toothless arrangements, Highwayman commits the biggest sin possible: it sounds like Music Row corporate product. It’s the antithesis of outlaw country. There’s no danger, there’s no edge, and there’s nothing that captures the true spirit of Johnny, Willie and Waylon (and Kris).

My best advice to you is to stay far, far away from this schlocky studio album and fire up The Highwaymen concert that’s always running on PBS (it’s in constant rotation along with “Roy Orbison & Friends in Black & White”) for a better experience with these country music legends.

[I’m obviously joking about Kris Kristofferson - he wrote Johnny’s best song - “Sunday Morning Coming Down” - and other classics like “For the Good Times”, but he’s a better songwriter and actor than performer, and that was Merle Haggard’s rightful spot.]

Pitch Failed (The Byrd’s version of “Deportee” is better)

CJ’s Response:

Many people think that creativity happens spontaneously, out of thin air. Like if you just get the right people and the right hallucinogenic drugs in the same room-Boom!-Ziggy Stardust. Having been a Creative Director in several ad agencies over the last 20-ish years, I can tell you this narrative is completely and utterly false.

The truth is that the best creative work starts with a great plan.

In advertising, no writer or art director thinks a single thought without being given a creative brief. The brief outlines many important aspects of the project, chief among them the “key message”. What is the one defining thing about our product or service that we want the audience to understand?

In short, what are we doing here?

This week’s album, Highwayman, features four country legends thrust into a recording studio without a creative brief.

In fairness, that’s only about 90% accurate. The album’s title song is far and away its best because it sounds like the four artists thought it through before they recorded it. If I had to guess, the rest of the album was the result of some coked-up producer hearing “Highwayman” and saying, “That was great, fellas! Now let’s lay down 8 or 9 more tracks and we’ll have ourselves an album. Play whatever you want—old songs you never finished, cover tunes, that poem you wrote on a cocktail napkin at the bar last night—we’ll make it work”.

It didn’t.

I’d be hard-pressed to pick my least favorite song on this record because there are so many worthy candidates. In an unintentionally prophetic twist, “The Last Cowboy Song” could easily have ended country music if enough people had heard it. “Jim, I Wore a Tie Today” is, I guess, a tribute to a fallen comrade whose funeral is the only reason these country boys would ever put on something as abhorrent as a necktie. And the cover of “Against the Wind” is enough to make Bob Seger put a silver bullet in his head.

If I had to pick a winner, though, it would be “The Twentieth Century is Almost Over.” The instrumentation and lyrics are so rudimentary that it feels like Schoolhouse Rock, only without the fun.

Ken, these four guys make the Top 10 of any country fan’s all-time list. But it just goes to show you, even the best cowboys need a plan.

Pitch Failed (I don’t like wearing ties either.)

Ken’s pitch was not successful and The Highwaymen’s Highwayman has been exiled to the end of the trail.

Blue eyes might be crying in the rain today, but you should walk the line to the comments section and let us know if you think Highwayman is for the good times or just outlaw shit.

Exile on Newbury St.

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