Top 10 Off-the-Beaten-Path Billy Joe Shaver & Willie Nelson Songs (In Honor of Today’s “Late Show” Appearance)

Awaiting the Flood is tremendously excited that two of our favorite artists, Billy Joe Shaver and Willie Nelson, will be tonight’s musical guests on The Late Show with David Letterman. Each musician has a new album out, Shaver with Long in the Tooth and, more recently, Nelson with Willie’s Stash, vol. 1: December Day.

Today, we wanted to do something special in honor of two superstars of outlaw country appearing together on television. No element of The Late Show has become more famous that Letterman’s “Top Ten” lists — a format Letterman himself helped to popularize far beyond Late Show Studios. With that in mind, Awaiting the Flood has commemorated tonight’s performance by compiling our own Top Ten list for the occasion.

Oh, sure, we could have just called it “Top 10 Billy Joe Shaver and Willie Nelson Songs,” loaded it up with the likes of “Wacko from Waco” and “On the Road Again” and called it day. But, anyone could do that. Instead, we poked around some of the dustier corners of the artists’ discographies to find two handfuls of off the beaten path gems: things you might not remember, or not have heard or even be aware exist.

Enjoy

#10.) “Hard to Be an Outlaw” by Billy Joe Shaver & Willie Nelson

If you haven’t heard this one, that’s likely because it’s still relatively new. This duet is one of the most memorable tracks on Shaver’s recent album, a delightful canvass for two of the most distinctive voices in outlaw country. On one level, the lyrics explore the challenges faced by an outlaw who has become, well, long in the tooth. On another level, the song also offers commentary on the current state of country music—with the two outlaw veterans getting in a dig or two at the genre’s contemporary mainstream.

#9.) “Warrior Man” by Billy Joe Shaver

Millions of America’s young hipsters have been exposed to Shaver’s music without even knowing it. Since 2005, the sounds of Shaver’s over-the-top (and rather gratuitously violent) honky tonk number “Warrior Man” have provided the perfect musical score to the opening sequence of Adult Swim’s cartoon “Squidbillies,” about a family of Appalachian cephalopods who are so country that they make Duck Dynasty seem like Downton Abbey.

#8.) “Family Bible” Willie Nelson

Written by Nelson in 1957 while working as a DJ in Washington, “Family Bible” was the turning point of Nelson’s career. Recorded by singer Claude Gray in 1960, the tune became a hit and Nelson suddenly found Nashville’s doors opening to him. Nelson would not record the song himself until 1971’s Yesterday’s Wine. Inspired by Nelson’s grandmother and written at a time when “outlaws” were bad guys at the Saturday picture show, “Family Bible” has a very traditional old-school country sound.

#7.) “Willy the Wandering Gypsy and Me” Billy Joe Shaver

What “Family Bible” was to Nelson, “Willy the Wandering Gypsy and Me” was to Shaver. In 1972, Waylon Jennings had invited Shaver to come to Nashville to record after hearing him perform the song at a festival in Texas. There’s more to it than that (nothing ever seems to come easily in Billy Joe Shaver land) but that’s the essence of the story. “Willy the Wandering Gypsy and Me” is a classic outlaw country song about the struggle between responsibility and the rambling impulse in all of us. This version, from a 1985 Austin City Limits broadcast, showcases Shaver’s vocals to particularly good effect.

#6.) “Hello Walls” Willie Nelson

Another title that was originally a songwriting rather than singing hit for Nelson. “Hello Walls” became a #1 hit for honky-tonk country singer Faron Young in 1961. Nelson used it as one of the tracks on his debut album, And Then I Wrote, the following year. It is impossible not to love this clip of Nelson performing the song on The Porter Wagoner Show.

#5.) “Cowboys Are Frequently, Secretly Fond of Each Other” Willie Nelson

A quarter century before “Brokeback Mountain” sent American’s art-house scene all atwitter, Willie Nelson was observing that ‘cowboys are frequently, secretly fond of each other’ and reminding us that, hey, that’s groovy. Video quality is poor on this link, but gets extra bonus points for being filmed at The Roundup Saloon, Dallas’s iconic Gay country/western dance hall.

#4.) “Window Rock” Billy Joe Shaver

The 2004 album, Billy and The Kid, was largely driven by Shaver’s efforts to come terms with the tragic and untimely death of his son, Eddy (and includes much of his son’s material, all hinting at a prodigious talent now lost). Through this process, Shaver provides some very unusual but worthwhile material. “Window Rock” may be the most atypically Billy Joe Shaver. Set a against a background of slow instrumentation and ethereal guitar work that sounds more prog rock than country—with some gentle western overtones. The song takes listeners on a surreal, stream-of-consciousness journey through images and events centering on Window Rock, Arizona, at the heart of the Navajo Nation.

#3.) “Red Headed Stranger” Willie Nelson

If you know even a little bit about country, you know Nelson’s nickname. But the eponymous 1975 recording seems surprisingly seldom heard, even among serious country fans. That’s a shame, “Red Headed Stranger” has all the beloved musical elements of Nelson’s slow outlaw ballads and is dripping with cowboy imagery. The irony, of course, is that the celebrated songwriter did not write the song that gave him his nickname. “Red Headed Stranger” was written by the team of Edith Lindeman and Carlton Stutz in 1953.

#2.) “The Hottest Thing in Town” Billy Joe Shaver

One of the finest fast honky-tonk songs ever recorded, I don’t know why this song, from Shaver’s 1993 album Tramp on Your Street, doesn’t get more love. An amorous ode to a not-so-angelic country queen, at times “The Hottest Thing in Town” segues into rockabilly territory and makes great use of Shaver’s fondness for spiritual imagery. This live performance at the storied Billy Bob’s Texas has some very fine electric guitar and Shaver is obviously having fun with the vocals.

And, the number-one off the beaten path Billy Joe Shaver or Willie Nelson song is…

#1.) “Honky Tonk Heroes” Billy Joe Shaver, Willie Nelson & Waylon Jennings

While a seminal Waylon Jennings album, Honky Tonk Heroes would never have happened without Shaver, who wrote or co-wrote or all but one of the album’s tracks. In hindsight, that the album got made seems like a miracle. While it was Jennings who invited Shaver to Nashville to write and record, by the time Shaver arrived Jennings appeared to either have forgotten or to be having second thoughts. According to Nashville folklore, after months of trying to find Jennings, Shaver eventually cornered him and threatened to fight him if Jennings would not listen to Shaver’s songs. Whether out of self-preservation or curiosity, Jennings gave in—and the result was Honky Tonk Heroes and a lot of other great music. Here is the album’s title track performed by three of the most remarkable voices in country music.

So, there you go, now you’re warmed up for Shaver and Nelson this evening.

The Late Show broadcasts 11:30 Eastern Time on CBS