Sony would be his last major label. Waymore's Blues (Part II) was eventually released by RCA in 1994, but it was recorded without Waylon having a label contract at all. RCA went on in 1996 to release a 20th anniversary edition of the immortal compilation, Wanted! The Outlaws featuring a newly recorded duet with Willie of Steve Earle's "Nowhere Man," and a 20-track compilation, The Essential Waylon Jennings featuring a previously unreleased track from the Waymore's Blues (Part II) sessions. Justice Records released 1996's Right for the Time, and Ark 21 released Waylon's final studio album Closing In on the Fire in 1998--by which point RCA's catalog imprint, Buddha Records, had begun to revive Waylon's catalog in a series of remastered re-issues.
Waylon also participated in two supergroups during the decade. In addition to his solo album, The Eagle, 1990 brought Highwayman 2, with Willie, Johnny Cash and Kris Kristofferson; their third and final collaboration as "The Highwaymen" came in 1995. In 1998 he teamed up with Bobby Bare, Jerry Reed and Mel Tillis as the "Old Dogs" for a live recording of Shel Silverstein compositions. Throughout the decade, Waylon guested on numerous artists's albums including Travis Tritt's "Outlaws Like Us" (also featuring Hank Williams, Jr.), a duet with Mark Chesnutt of Waylon's "Rainy Day Woman" and even a Neil Diamond recording of "One Good Love."
Note that I have excluded from this list 1992's Ol' Waylon Sings Ol' Hank, which was re-issued in 2006, because the recordings themselves were made in 1985 and I intend to include selections from that collection when I work on a Waylon in the 80s playlist. I have also excluded 1993's children's album, Cowboys, Sisters, Rascals and Dirt for the simple reason I don't have it in my library (I know, I know!). Which reminds me: you may run into trouble looking for the original albums as several of them are out of print. I suggest you actually go to your local record shop. They may just have what you're looking for and they could use the business.
Here, then, are what I feel are the gems of Waylon's often overlooked 90s output. Given the numerous labels involved, I suspect we'll never see an official compilation released that will survey this decade and that's a shame. Waylon sounded just as good then as he ever did. And give the man credit for one important thing: he was still writing and recording original material even at what would prove the end of his career. It's rare for artists to still be working at all at that point, and many of those who do find themselves re-recording the songs that made them famous, or even going back and exploring the Great American Songbook. But then, surely no one expected the trailblazer who fought Nashville to be content covering familiar ground?
Closing In on the Fire (1998) - The sound of this song is unlike anything else; it's clear from the opening notes that this is Waylon as you haven't heard him before and his deep vocals growl through this raw, sexual song written by Tony Joe White.
"The Eagle" from The Eagle (1990) - A top 5 hit written about Desert Storm. Waylon didn't bang the war drum often and he typically shied away from politics in his music, but here he manages to do something that a lot of today's artists could learn from: he wrote thoughtful lyrics such as, "Just because I've been idle/don't mean I don't care."
"Wild Ones" from Waymore's Blues (Part II) (1994) - Looking back is a theme often explored by older artists, and Waylon was no exception. This is one of the stronger reminisces from this period.
If I Can Find a Clean Shirt (1991) - Waylon and Willie, goading each other into "going down on the border tonight/drinkin' tequila, taking chances on our lives." The music video to this was sheer fun.
"What Bothers Me Most" from The Eagle - Waylon cuts to the bone here, languishing over an already cold relationship.
"Her Man" from The Eagle - Country fans are probably more familiar with Gary Allan's cover of this, but Waylon did it first. It's up to you to decide who did it better, but I'll tell you this: when Waylon tells me "I've had misadventures/I've even got pictures," I believe him.
Old Dogs - Maybe going to Mexico with Willie finally caught up to Waylon. On this Shel Silverstein track, the Old Dogs recognize their limitations.
"I Know About Me, I Don't Know About You" (duet with Travis Tritt) from Closing In on the Fire - Few of the new guard of artists who were part of the 90s country boom were as unabashed about their admiration for the older artists than Tritt. The clashing of old honky tonk steel and new rock guitar as the two trade off here is a microcosm of that symbiosis. (How's that for showin' off my vocabulary?)
"Angels Love Bad Men" (with Johnny Cash, Kris Kristofferson and Willie Nelson) from Highwayman 2 - I picked this because it was the only song from that album written by Waylon.
"Smokey on Your Front Door" from Too Dumb for New York City, Too Ugly for L.A. - Just a fun little romp of a song, and one of the livelier tracks from what I'm sorry to say is a rather weak album.
"The Boxer" from Right for the Time - Waylon covering Paul Simon? Yes. And he kills it.
"The Devil's Right Hand" (with Johnny Cash, Kris Kristofferson and Willie Nelson) from The Road Goes On Forever - Waylon loved this Steve Earle song so much he recorded it by himself for his 1986 album, Will the Wolf Survive. I love the energy here, and Earle's thoughtful, weary lyrics are done justice by the foursome.
"Nobody Knows" from Waymore's Blues (Part II) - A silly novelty song in which Waylon informs us that he's really Elvis. This could easily have been a dud, but the energy level is high from start to finish and Waylon's clearly having fun with it.
Whatever Happened to the Blues" from The Essential Waylon Jennings - Waylon had an affinity for the blues, which he demonstrated on numerous recordings throughout his career. This might be the best of them, and anyone who thinks Waylon could only have been a country singer need look no further than this recording to see he could have just as easily made it as a Southern blues singer.
"Nowhere Road" (duet with Willie Nelson) from Wanted! The Outlaws - 20th Anniversary Edition - Another Steve Earle song. Waylon and Willie, in their final studio recording together. Fans should buy the album just for Earle's liner notes. Seriously.
Outlaw Country: Live in Austin TX - Something of a cheat here. This is from a 1996 episode of Austin City Limits featuring Waylon, Kris, Willie, Billy Joe Shaver and Kimmie Rhodes in a guitar pull. Waylon performed three songs, but this in particular I wanted to highlight. Waylon rarely covered religion in his music, which makes this song detailing his theological philosophy unique in his discography. What's more is that the only other recording he did of the song was with the Highwaymen, making this the only existing recording of Waylon singing the song entirely by himself. Kristofferson selected it for his contribution to a 2003 tribute to Waylon.
What a Way to Live - Chesnutt named his next born son for Waylon after Hoss agreed to contribute to this cover of his old song. There's an additional verse that, to my knowledge, only appears in this duet version of the song.
"I Ain't Song (Acoustic Demo)" from The Road Goes On Forever - 10th Anniversary Edition - Waylon performs the song about the then-current state of country music for his fellow Highwayman, much to their amusement. A studio version was included on Right for the Time with the title, "Living Legends (Part II)." I favor this version just to hear Kristofferson's reaction at the end.
"Shine on Me" (duet with Andy Griggs) from You Won't Ever Be Lonely - Waylon co-wrote this with Beth Nielsen Chapman. I can't be sure, but based on my research this duet version with Griggs--on his debut album--appears to be the only recording of the song by Waylon. How's that for generosity?
I Never Cared for You" from Twisted Willie: A Tribute to Willie Nelson - Waylon and Cash were the only country artists to contribute to this alternative rock tribute to their friend. Waylon's vocals here are haunting.
"Kissing You Goodbye" from Right for the Time - Waylon finds the humor in breaking up. I selected it as the final track here to embrace a sense of optimism rather than weary finality as we conclude our survey of Waylon's final decade as a studio recording artist.