The Waylon Jennings Vinyl Box Set Worth Knowing About — And the Eight-Year Fight Behind It

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In the summer of 1972, Waylon Jennings was lying in a Nashville hospital bed with hepatitis, broke, strung out on amphetamines, and seriously considering quitting music altogether. The deal RCA offered him to keep going was the same nickel-and-dime royalty rate he’d signed in 1965: five percent, a $5,000 bonus, take it or leave it. He left it. What happened next — a new manager, a rewritten contract, and eight years of albums made almost entirely on his own terms — is the exact run of records that Vinyl Me, Please collected into a 1,000-copy vinyl box called The Story of Waylon Jennings.

This is not breaking news. The box has been out since the fall of 2023, pressed on 180-gram colored vinyl and remastered from the original analog tapes by Ryan Smith at Sterling Sound. But “Essentials” was never supposed to mean “new” — it means worth owning, and worth understanding before you spend the money. Andrew Winistorfer, the set’s executive producer, put it plainly when VMP announced the project: he wanted to present “arguably the best run of studio albums in country music history” in a format that finally did the recordings justice. That is a big claim. It also happens to be defensible, track by track, once you know what actually happened inside RCA’s Nashville studios between 1973 and 1981.

Here is the short version of why those eight albums exist at all, what’s actually pressed inside the box, and where a collector should spend real money versus where a single well-chosen compilation does almost as much good. It’s a story with a hospital bed, a locked-up recording studio two blocks off Music Row, a platinum record the industry didn’t see coming, and an arrest that produced one of the most self-aware songs of Jennings’s career — all of it happening inside eight years, almost all of it on tape that Vinyl Me, Please’s engineers have now gone back and cleaned up properly.

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The RCA Contract Fight That Made Waylon Jennings an Outlaw

To understand why eight albums made under one contract renegotiation are worth an entire reissue campaign fifty years later, you have to understand what Nashville sounded like before them. By the early 1970s, the dominant commercial approach — generally called the Nashville Sound — favored lush string arrangements, polished background vocals, and a stable of A-list session players rotating through every major artist’s records, all overseen by staff producers who picked the material and ran the sessions. It made hits. It also meant most country artists, however famous, had remarkably little say over what their own records actually sounded like. Waylon Jennings spent most of the 1960s working exactly inside that system. Before any of this was a genre with a name, it was a sick man in a hospital bed making a decision about money. Jennings had been a working RCA artist since the mid-1960s, grinding out roughly three hundred nights a year on the road, running up debt, and leaning harder on amphetamines just to keep standing — “pills were the artificial energy on which Nashville ran around the clock,” he said later, and he meant it as description, not excuse. By 1972 the hepatitis diagnosis had him weighing retirement outright. His drummer, Richie Albright, talked him out of it and pushed him toward a New York music-business lawyer and manager named Neil Reshen.

Reshen did two things that mattered more than almost anything else in this story. First, he rejected RCA’s lowball renewal — the same 5 percent royalty rate Jennings had been stuck with since 1965 — and negotiated a new deal that actually reflected what Jennings was worth to the label: a $75,000 advance and, critically, real artistic control over his own recordings. Before that renegotiation, Jennings’s producers didn’t let him pick his own songs or even play his own guitar on his own records. Second, Reshen looked at the beard Jennings had grown during his hospital stay and told him to keep it. It fit, he said, the image they were about to build.

One name is worth tracking through this entire story, because he shows up at nearly every turn: Richie Albright, Jennings’s longtime drummer and touring bandleader. It was Albright who talked Jennings out of retiring in that hospital room in 1972. It was Albright’s touring band — not a rotating cast of Nashville session players — that Jennings fought to use on his own studio records once the new contract gave him the right to choose. And it would be Albright, years later, who disposed of the cocaine mailed to Jennings during the 1977 arrest while federal agents waited outside for a search warrant. A reissue box like this one tends to center the singer whose name is on the spine, but almost none of it happens without the bandmate standing next to him the entire time.

That image needed a sound to go with it, and Jennings found it almost immediately. For the record that would define the era, he pulled in Tompall Glaser to co-produce in place of his longtime RCA producer Chet Atkins, and he filled the album almost entirely with songs by a broke, mostly unknown Texas songwriter named Billy Joe Shaver. The result, Honky Tonk Heroes, arrived in the summer of 1973 — raw, loose, closer to a bar band than a Nashville session — and Shaver himself later called it “the touchstone of the Outlaw movement.” Rolling Stone praised its “crisp, robust no-nonsense sound” at the time; five decades later it’s still routinely named one of the essential records of the era, included in 1001 Albums You Must Hear Before You Die.

“Pills were the artificial energy on which Nashville ran around the clock.”

Waylon Jennings

Honky Tonk Heroes is the record that defined the era, and it is not in the box. Vinyl Me, Please’s anthology skips it and opens instead with Lonesome, On’ry and Mean, which Jennings released earlier the same year. They were the first two albums he made under his new creative control, recorded almost back to back, and together they’re the reason the next eight years of his catalog sound like nobody told him no.

A lot of that creative control had an actual address: 916 19th Avenue South in Nashville, about two blocks off Music Row, a two-story stucco building that Tompall Glaser had built with money his own group, the Glaser Brothers, had earned from their earlier country success. A New York music journalist nicknamed it “Hillbilly Central” in 1974, and the name stuck because it was accurate. The first floor held offices and apartments; the second floor held a recording studio that was genuinely state-of-the-art for the period. The shutters stayed closed around the clock, people came and went at all hours, and sessions ran on nobody’s schedule but the artists’ own — the exact opposite of how RCA’s own Studio B operated just down the road, where staff producers controlled the songs, the musicians, and the clock. Jennings recorded there. So did Billy Joe Shaver, Kris Kristofferson, Jimmy Buffett, Kinky Friedman, John Hartford, Shel Silverstein, and Mickey Newbury, among others, at various points.

The word “outlaw” itself has a specific, disputed origin story that traces back to that same building. The most widely repeated account credits Hazel Smith, Glaser’s secretary at Hillbilly Central, with pulling the term from a dictionary definition — someone who lives outside the conventional law of the land — and applying it to the artists working there who had, in a very literal contractual sense, stepped outside Nashville’s usual way of doing business. A newsletter she wrote using the word is often cited as the first time it stuck to this specific group of musicians in print. Not everyone agrees on the credit; one persistent counter-claim points instead to Dennis Glaser’s own dictionary research inside the building. Either way, the label was coined inside the same walls where these records were being made, which is a more honest origin story than most marketing campaigns ever get.


Also on Classic Country TV: Fifty years ago this same outlaw circle put out country’s first platinum album — and almost none of it was recorded the way the liner notes imply. Read where every track on “Wanted! The Outlaws” really came from


It’s worth sitting with how unusual this was. In 1973 Nashville ran almost entirely on a factory model: A&R men and staff producers picked the songs, hired the session players, and controlled the final mix, and an artist’s job was mostly to show up and sing well. Jennings didn’t just get a bigger advance out of Reshen’s renegotiation — he got the right to choose his own material, use his own touring band in the studio instead of A-list session players, and walk out of a session he didn’t like. Almost no one at a major Nashville label had that kind of leverage in 1972. The eight albums collected in the Vinyl Me, Please box are, in a very literal sense, the sound of a man spending that leverage for nearly a decade before the record company found a way to rein him back in.

None of it was free of cost. Jennings had been using amphetamines since the mid-1960s, during the years he lived with Johnny Cash, and the road work that funded his new independence only deepened the habit. He carried a private weight the whole time, too: by his own account in later years, he felt responsible for the 1959 plane crash that killed Buddy Holly, his friend and former bandleader, after Jennings gave up his seat on the chartered plane — a guilt that fed years of substance abuse he didn’t fully address until 1984. The outlaw image RCA’s marketing department would eventually sell by the truckload wasn’t a costume. It was closer to a documentary.

Eight Albums, One Creative Streak: What’s Actually in the Box

Here is exactly what Vinyl Me, Please pressed, in the order the albums were originally released. This is the part worth printing out and keeping next to the turntable, because it’s the single clearest map of how fast and how far Jennings moved once nobody was stopping him.

Lonesome, On’ry and Mean (1973) — one of the first two albums Jennings made under his new creative control, built on a raw, road-worn cover of Steve Young’s title song that gave the whole run its unofficial name.
This Time (1974) — produced by Jennings and Willie Nelson at Glaser Sound, built around a self-penned title track that became Jennings’s first No. 1 single.
The Ramblin’ Man (1974) — released the same year, featuring “I’m a Ramblin’ Man,” one of the signature outlaw-era road songs and a No. 1 country single.
Dreaming My Dreams (1975) — Jennings’s own favorite of his catalog, produced with Jack Clement, certified his first RIAA Gold record, and later ranked No. 2 on Rolling Stone’s list of the 100 Greatest Country Albums of All Time.
Are You Ready for the Country (1976) — featuring Jennings’s own take on the Neil Young title track, a cross-genre cover that signaled how far outside Nashville’s usual boundaries he was willing to reach.
Ol’ Waylon (1977) — the home of “Luckenbach, Texas (Back to the Basics of Love),” his biggest crossover hit and the song most casual fans would name first if you said his name.
I’ve Always Been Crazy (1978) — written in the direct aftermath of his 1977 cocaine arrest, including “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” a song that is as close as Jennings ever came to commenting on his own myth in real time.
Leather and Lace (1981) — a duets album with his wife, Jessi Colter, closing out the run on a domestic note after nearly a decade of increasingly public outlaw mythology.

Historical recreation of Waylon Jennings, age 37, and producer Jack Clement at Glaser Sound Studios in Nashville in 1974, working at a mixing console with reel-to-reel tape machines
Waylon Jennings, 37, and producer Jack Clement at Glaser Sound Studios in Nashville, 1974, during the sessions for “Dreaming My Dreams” — the album Jennings himself called his favorite. Historical recreation.

The two records that open the set are worth a closer look, since they’re the ones most casual fans have genuinely never heard. Lonesome, On’ry and Mean, released in 1973, gave the whole era its unofficial name and its attitude in roughly equal measure, and it arrived earlier that year than Honky Tonk Heroes, not after it. This Time, released in 1974, was produced by Jennings and Willie Nelson at Glaser Sound, and its unhurried, almost conversational title track — written by Jennings himself, about the wreckage of his own marriages — gave him his first No. 1 single and set the tone for the more relaxed, personal songwriting voice that would carry through the rest of the box. Together they’re where you can hear Jennings figuring out what his newfound creative freedom was going to sound like, in real time, before he’d fully found it.

Look at that list again and the math gets genuinely hard to argue with: eight studio albums in eight years, one RIAA Gold certification already locked in by the midpoint, and a direct line to the two platinum records — Wanted! The Outlaws and Ol’ Waylon — that follow immediately after. Most working artists need a greatest-hits package to cover that much ground. Jennings did it with original studio material, almost all of it written or co-written inside his own circle, released on a schedule that would exhaust most contemporary artists’ entire careers.

Dreaming My Dreams deserves its own paragraph, since Jennings named it his personal favorite among everything he ever recorded and the historical record backs up his judgment. Produced with Jack Clement across sessions running from February to July of 1974 at Glaser Sound Studios, it topped the country albums chart, earned Jennings his first RIAA Gold certification, and won him the Country Music Association’s Male Vocalist of the Year award in 1975. The single “Are You Sure Hank Done It This Way” hit No. 1 on the country singles chart and became something close to an outlaw-movement mission statement — a direct question about whether Nashville’s polished, string-heavy “Nashville Sound” was really what Hank Williams himself would have recognized as country music. Decades later, Rolling Stone ranked it No. 2 on its 2022 list of the 100 Greatest Country Albums of All Time, behind only Dolly Parton’s Coat of Many Colors — a startling placement for a record most casual fans have never heard of, and a strong argument on its own for why this specific run deserved the reissue treatment.

The chart record backs up exactly how fast this moved. “I’m a Ramblin’ Man,” written by Ray Pennington, gave Jennings a No. 1 country single off The Ramblin’ Man in 1974. Two years later, Are You Ready for the Country — produced by Jennings alongside Ken Mansfield, whom RCA initially balked at and Jennings brought in at his own expense — reached No. 1 on the country albums chart and went Gold. The album’s opening title track is itself a small statement about how far outside Nashville’s usual boundaries this run was willing to reach: a cover of a Neil Young song from Young’s 1972 album Harvest, recorded by a mainstream country star at a moment when country radio and rock radio treated each other as separate, mostly hostile countries. Ol’ Waylon, produced the next year by Chips Moman, topped the country albums chart for thirteen straight weeks, became Jennings’s fourth consecutive solo No. 1 country album, and reached No. 15 on the all-genre Billboard 200.

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From “Honky Tonk Heroes” to Country’s First Platinum Album

The commercial proof of everything this run was building toward arrived in January 1976, when RCA released Wanted! The Outlaws — technically a compilation, pulling together previously released and new material from Jennings, Willie Nelson, Tompall Glaser, and Jessi Colter under a single marketing umbrella built around the word “outlaw” itself. It became the first country album certified platinum by the RIAA. It won the Country Music Association’s Album of the Year award that same year, credited to all four artists, and its Jennings–Nelson duet “Good Hearted Woman” took the CMA’s Single of the Year.

That milestone didn’t appear out of nowhere. It landed about three and a half years after Jennings fought his way out of RCA’s standard contract terms, and it is impossible to separate from the eight studio albums collected in the Vinyl Me, Please box — several of which supplied the very tracks Wanted! The Outlaws repackaged for a wider audience. The follow-up solo album, Ol’ Waylon, went platinum the next year on its own, a first for any solo artist in country music at the time. Two platinum records inside two years, arriving directly out of a run most label executives in 1972 would have bet against.

Historical recreation publicity portrait from February 1976 showing Waylon Jennings, 38, Willie Nelson, 42, Jessi Colter, 32, and Tompall Glaser, 42, standing together outside an RCA Nashville studio building
Waylon Jennings, 38, Willie Nelson, 42, Jessi Colter, 32, and Tompall Glaser, 42, outside RCA’s Nashville studios in February 1976, the year “Wanted! The Outlaws” became country music’s first platinum album. Historical recreation.

“Luckenbach, Texas (Back to the Basics of Love),” the centerpiece of Ol’ Waylon, is the song that carried the outlaw movement out of its own subculture and onto mainstream pop radio — a Willie Nelson guest turn, a chorus built around a tiny real Texas town most listeners had never heard of, and a message that cut directly against the gun-and-whiskey outlaw caricature RCA’s own marketing had helped build: that the whole point, after everything, was gettin’ back to the basics of love. Written by Bobby Emmons and Chips Moman — the same Moman who produced the album — the single was released on April 11, 1977, debuted on the country charts five days later, and held No. 1 from May 21 through June 25 of that year, while also reaching No. 25 on the pop charts. It remains, by a wide margin, the biggest hit single of Jennings’s career, and he never liked it: in his autobiography he wrote that he knew it was a hit when he cut it and still didn’t care for it two decades later. He hadn’t even visited the real Luckenbach when he recorded it; he didn’t get there until he played Willie Nelson’s Fourth of July Picnic in 1997. It is also the rare outlaw-era song that works as both anthem and quiet correction of the myth surrounding it.

The cultural footprint of this stretch is easy to understate because it happened so fast. In the space of roughly five years, outlaw country went from a handful of artists fighting their own labels for the right to pick their own songs to a certified commercial format with its own platinum sales records, its own CMA trophy, and its own permanent place in how country music tells its history. Jennings and his circle didn’t just make a run of good albums. They proved, with hard sales numbers RCA couldn’t argue with, that an artist could win that fight and still sell more records than the system that tried to stop him.


Also on Classic Country TV: The same chart-topping circle of outlaws shows up again and again in the week country radio handed them its biggest trophy.
Read the week “Wanted! The Outlaws” won Album of the Year


None of that success made the toll disappear. Jennings’s cocaine use, already present through the mid-1970s, intensified through the end of this run and into the early 1980s — the period that produced Leather and Lace, the box set’s final entry. On August 23, 1977, federal agents arrested him in Nashville for conspiracy and possession of cocaine with intent to distribute, after 27 grams were mailed to him by a colleague; his drummer disposed of the drugs while investigators waited outside for a search warrant, and the charges were ultimately dropped. He wrote about the arrest almost immediately, with the kind of blunt self-awareness that made his songwriting what it was — “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” released the following year on I’ve Always Been Crazy. He didn’t get clean until 1984, crediting his young son Shooter as the reason he finally stopped. Jennings himself later called the entire outlaw movement “a self-fulfilling prophecy” — a label that, once the public bought it, he had to keep living up to, whether or not it was good for him.

That is the real shape of this catalog: not an outlaw costume, but eight years of a documented, difficult, genuinely era-defining stretch of work, made by a man paying a steep personal price for the independence he’d fought RCA to get. Collecting the records is one thing. Understanding what they actually cost to make is what separates a casual Waylon Jennings fan from someone who has actually sat with this part of his story.

I’ve Always Been Crazy, the album built directly out of that arrest, deserves to be heard as exactly what it is: a man publicly narrating his own unraveling while it was still happening, in real time, on a major-label record. The title track alone — “I’ve always been crazy, but it’s kept me from going insane” — reads less like outlaw bravado and more like someone trying to talk himself through a genuinely difficult stretch using the only tool he had, which was songwriting. “Don’t You Think This Outlaw Bit’s Done Got Out of Hand” goes even further, essentially asking the audience the same question this article is built around: at what point does a marketing label stop describing an artist and start controlling him. Few artists in any genre have ever been quite that direct about the cost of their own image, this close to living through it.

The influence didn’t stop with Jennings’s own generation, either. The specific fight this box set documents — an artist demanding the right to pick his own songs, use his own band, and reject a label’s idea of what “sells” — is the same fight a long line of later country artists have had to have with Nashville all over again, from the 1990s alt-country underground through the more recent wave of artists who built entire careers partly on the promise of creative independence from mainstream Music Row. Every time a contemporary artist gets praised for “doing things their own way,” it’s worth remembering there’s a documented, dated paper trail showing exactly when and how that particular fight was first won at a major Nashville label, and whose name is on the contract.

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Collecting It Right: What Vinyl Me, Please Actually Pressed

Vinyl Me, Please built The Story of Waylon Jennings as the 18th installment of its Anthology series — the same format the company had already used for a Willie Nelson box, which Winistorfer pointed to directly as the project’s predecessor. That sequencing isn’t a coincidence: Jennings and Nelson spent the exact years covered by this box set building their public partnership, from the shared credit on Wanted! The Outlaws through Nelson’s turn on “Luckenbach, Texas,” so a label building a serious outlaw-country reissue program was always going to end up doing both artists’ catalogs eventually. The pitch for the Jennings box was straightforward: these albums hadn’t been reissued all-analog in years, and in some cases ever, the copies you find in record stores are mostly well-loved and beat up, and a catalog this strong deserved an audiophile-grade treatment rather than another cheap, scattered reissue. Working with Jennings’s estate and Legacy Recordings, VMP put all eight albums — Lonesome, On’ry and Mean through Leather and Lace — on 180-gram colored vinyl, remastered from the original analog tapes by mastering engineer Ryan Smith at Sterling Sound, and limited the first edition to 1,000 boxes. The jackets are faithful tip-on recreations, and each box also carries a 28-page photo booklet of listening notes; VMP produced a companion podcast that walks through the albums one by one.

That mastering credit is worth pausing on if you don’t follow vinyl production closely. Sterling Sound is one of the oldest and most respected mastering houses in American recorded music, and remastering “from the original analog tapes” is not a marketing phrase — it means going back to the actual session reels rather than a decades-old digital file, re-cutting the record to pull out detail and dynamic range that a cheap reissue, working from a compressed master, simply cannot recover. For a catalog this personal — made under genuine creative-control pressure, in sessions where Jennings was finally choosing his own takes — hearing it the way the tape actually captured it is not a small upgrade.

It’s also worth giving Leather and Lace, the box’s final and most overlooked entry, its own moment. Jessi Colter had her own substantial solo career before and during her marriage to Jennings — her 1975 single “I’m Not Lisa” topped the country chart and crossed into the pop top five, a bigger pop breakthrough than almost anything her husband managed on his own. By 1981, closing out this eight-album run with a full duets record alongside his wife wasn’t a victory lap so much as a quiet correction: after nearly a decade of increasingly mythologized outlaw branding, the last record in the box is two people who were actually married, singing to each other.

That scarcity is worth being honest about upfront: this is a direct-to-member release, sold through Vinyl Me, Please’s own membership platform rather than general retail, and it has been out since the fall of 2023. If you’re reading this hoping to buy it new today, Vinyl Me, Please’s own product page is the place to check current availability and membership terms directly — as of October 18, 2026, the page was still live and listed the set as a members-only title. If it has sold through, the realistic path is the secondary market, where Discogs and eBay show copies changing hands, rather than a fresh pressing run. Stock on a 1,000-copy limited run changes without much warning.

For anyone who isn’t going to chase a box on the secondary market, there’s a completely legitimate second path into this exact catalog: pick up the individual studio albums, or a well-assembled hits compilation drawing from the same years, in whatever pressing you can actually find. The important thing a collector should take from this story isn’t “buy this one specific box.” It’s “these eight years of Waylon Jennings records are worth owning in some physical form, remastered or not” — and that’s a much easier, much cheaper goal to accomplish.

That’s also exactly where the gear picks below come in. Rather than send you chasing a limited run, we’ve pulled together Waylon Jennings vinyl pressings that draw on this same stretch of his catalog, plus the turntable and cleaning gear that actually matters once you own records worth protecting. None of it requires winning an eBay auction.


Also on Classic Country TV: If this is the album run that got you thinking seriously about your collection, the actual work starts with knowing which pressings are worth the money. Read our guide to must-own vinyl pressings for traditional country collectors


A remaster is also only as good as the system playing it back. A worn stylus or a cheap all-in-one suitcase player will flatten the exact dynamic range Ryan Smith’s remastering was built to restore — which is part of why a serious collector’s first upgrade is almost always the turntable and cartridge, not another record.


Also on Classic Country TV: The stylus is the only part of your setup that physically touches the record — and it’s the one upgrade most new collectors skip first. Read our complete guide to the best phono cartridges for classic country vinyl


Historical recreation still-life of a vinyl album in a plain sleeve leaning against a turntable, with a stack of LPs beside it on a wooden table
The eight-album run collected in Vinyl Me, Please’s box represents nearly a decade of Waylon Jennings working almost entirely on his own terms. Historical recreation.

Why It Still Matters

It would be easy to file this story under nostalgia for a record label fight that ended before most of today’s country radio audience was born. That would miss the actual point. Every artist working today who has ever fought a label, a streaming platform, or a management company for the right to control their own material is standing, whether they know it or not, on ground Waylon Jennings and Neil Reshen cleared in a Nashville hospital room in 1972. The eight albums in this box aren’t just a strong run of records. They’re the documented proof that the fight was winnable, and that winning it could sound this good.

That’s also why a 1,000-copy limited vinyl box matters beyond the collectors who manage to track one down. Vinyl Me, Please’s decision to remaster all eight albums from the original analog tapes — rather than cheap, compressed digital masters — is a preservation choice as much as a commercial one. Working directly with Jennings’s estate to get it right means this specific, hard-won stretch of his catalog won’t simply fade into out-of-print used-bin obscurity the way so much of the era’s back catalog already has.

Jennings is also back in circulation in a way that would have been hard to predict. His son Shooter Jennings has been curating albums built from unheard Waylon recordings, starting with Songbird in October 2025; a second collection, Diamonds, is due November 13, 2026. A posthumous star on the Hollywood Walk of Fame has also been announced for the class of 2027. None of that replaces the eight albums in this box. It’s more evidence that the work was bigger than the fight that made it possible.

Hillbilly Central didn’t last forever, either. Jennings and Tompall Glaser eventually had a falling-out — the historical record is thin on exactly why — and the studio that had briefly been, by most accounts, the single most important renegade recording room in country music history faded from its peak years. It’s a fitting, slightly sad footnote to a movement built partly on the idea that nobody could tell these artists what to do: eventually, that applied to each other too. The building still stands at 916 19th Avenue South in Nashville, and it’s still a recording facility, the home of Compass Records. Nothing about the exterior tells you what happened on the second floor in the 1970s, which is exactly the kind of quiet erasure a publication like this one exists to push back against.


Also on Classic Country TV: The man who built the room where all of this happened has barely made the history books. Read the story of Tompall Glaser, the man who built Hillbilly Central


The job of a publication like this one isn’t to tell you to go find one specific limited-edition box set. It’s to make sure the story behind it — the hospital bed, the sidelined producer, the cocaine arrest, the platinum records, the song he wrote about his own myth — doesn’t disappear just because the records themselves are hard to find. However you end up hearing these eight albums, whether that’s a Vinyl Me, Please box picked up secondhand, a battered original RCA pressing found in a bargain bin, or one of the readily available compilations drawing from the same years, hear them knowing what they actually cost to make. That’s the whole point of calling something essential: not that it’s rare, but that it’s worth the effort of finding at all.


Gear Inspired by the Story

CDs & Vinyl

Waylon Jennings — Greatest Hits, Vol. 2 (Vinyl LP, RCA)
Drawing heavily on the second half of this exact run — the mid-to-late-1970s hits that followed “Luckenbach, Texas” — this is a readily available entry point into the catalog while the Vinyl Me, Please box stays a scarce, direct-to-member release.
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Waylon Jennings — Nashville Rebel (Vinyl LP, RCA)
A compilation pulling from across Jennings’s RCA years, useful as a second, complementary entry point for a collector building out this stretch of his catalog one available pressing at a time.
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Listening & Audio

Audio-Technica AT-LP60X-BK Fully Automatic Belt-Drive Turntable
A genuinely capable, affordable starting turntable — the difference between hearing what a proper remaster actually sounds like and hearing it through a toy suitcase player.
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Spin-Clean Record Washer Complete Kit
The single best investment a new collector can make before chasing original pressings — it gets decades of grime out of the grooves instead of grinding it in with a dry cloth.
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Vinyl Storage & Home Decor

Crosley Furniture Liam Small Mid-Century Modern Record Player Stand (Walnut)
A proper home for a turntable and a growing stack of outlaw-era records, instead of a milk crate on the floor.
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Crosley Furniture Asheville Mid-Century Modern Media Console (Walnut)
A larger storage console for a collection that’s outgrowing the starter shelf — built with the same vinyl-era aesthetic this whole catalog comes from.
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From the CCTV Shop


Sources

Rolling Stone — Announcement of Vinyl Me, Please’s “The Story of Waylon Jennings” box set, including Andrew Winistorfer’s quote on the album run and pressing/edition details.
https://www.rollingstone.com/music/music-country/the-story-of-waylon-jennings-box-set-1234770411/

Uproxx — Additional reporting on the box set’s announcement, track listing, remastering credits, and the connection to VMP’s prior Willie Nelson anthology.
https://uproxx.com/indie/waylon-jennings-vinyl-me-please-box-set/

Vinyl Me, Please — Official product page for “The Story of Waylon Jennings,” with album list, format, booklet and podcast details, and membership availability.
https://www.vinylmeplease.com/products/the-story-of-waylon-jennings

Discogs — Release-level details confirming the box set’s November 2023 release, catalog numbers, and edition format.
https://www.discogs.com/sell/release/28880344

Wikipedia — Waylon Jennings — Biographical reference covering the 1972 RCA contract renegotiation, Neil Reshen, the 1977 cocaine arrest, his marriage to Jessi Colter, and his substance-abuse history and recovery.
https://en.wikipedia.org/wiki/Waylon_Jennings

Wikipedia — Honky Tonk Heroes — Album-level detail on the 1973 release, Billy Joe Shaver’s songwriting contributions, and the record’s role in defining outlaw country.
https://en.wikipedia.org/wiki/Honky_Tonk_Heroes

Wikipedia — Dreaming My Dreams (Waylon Jennings album) — Chart performance, production credits, Gold certification, and critical reception, including its ranking on Rolling Stone’s 100 Greatest Country Albums list.
https://en.wikipedia.org/wiki/Dreaming_My_Dreams_(Waylon_Jennings_album)

Wikipedia — Wanted! The Outlaws — Details on the 1976 compilation’s platinum certification, CMA Album of the Year win, and the follow-up platinum certification of “Ol’ Waylon.”
https://en.wikipedia.org/wiki/Wanted!_The_Outlaws

Wikipedia — This Time (Waylon Jennings album) — Production credits (Jennings and Willie Nelson), the Glaser Sound recording sessions, and the title track’s songwriting credit.
https://en.wikipedia.org/wiki/This_Time_(Waylon_Jennings_album)

Wikipedia — Ol’ Waylon — Thirteen weeks at No. 1 on the country albums chart, the platinum certification, and the album’s chart peaks.
https://en.wikipedia.org/wiki/Ol%27_Waylon

Rolling Stone — “The 100 Greatest Country Albums of All Time” (2022), placing Dreaming My Dreams at No. 2 behind Dolly Parton’s Coat of Many Colors.
https://www.rollingstone.com/music/music-lists/best-country-albums-1234581876/

American Songwriter — On “Luckenbach, Texas”: Jennings’s dislike of the song, the six-week No. 1 run beginning May 21, 1977, and his first visit to the town in 1997.
https://americansongwriter.com/on-this-day-in-1977-waylon-jennings-started-a-six-week-run-at-no-1-with-a-song-he-never-liked/

American Songwriter — The 1976 CMA winners, confirming Wanted! The Outlaws as Album of the Year for all four artists.
https://americansongwriter.com/3-cma-winners-from-1976-we-still-cant-get-enough-of-today/

Compass Records — History of the former Glaser Sound / Hillbilly Central building at 916 19th Avenue South and its current use as a recording studio.
https://compassrecords.com/studio/

American Songwriter — Report on Shooter Jennings’s archive series and the November 13 release of Diamonds.
https://americansongwriter.com/more-than-20-years-after-his-death-new-recordings-from-a-defining-figure-of-the-outlaw-country-movement-surface/

American Songwriter — Announcement of Waylon Jennings’s posthumous star in the Hollywood Walk of Fame class of 2027.
https://americansongwriter.com/waylon-jennings-to-be-honored-with-posthumous-star-on-the-hollywood-walk-of-fame/

Frequently Asked Questions

What is “The Story of Waylon Jennings” box set?

It’s an 8-LP vinyl box set released by Vinyl Me, Please in November 2023, the 18th installment of the company’s Anthology series. It collects eight Waylon Jennings studio albums from 1973 to 1981, remastered from the original analog tapes by Ryan Smith at Sterling Sound and pressed on 180-gram colored vinyl, with a first edition limited to 1,000 copies.

Which albums are included in the Vinyl Me, Please Waylon Jennings box set?

The box includes Lonesome, On’ry and Mean (1973), This Time (1974), The Ramblin’ Man (1974), Dreaming My Dreams (1975), Are You Ready for the Country (1976), Ol’ Waylon (1977), I’ve Always Been Crazy (1978), and Leather and Lace (1981), a duets album with Jessi Colter.

Why is Waylon Jennings’ 1973–1981 run considered his creative peak?

After a 1972 contract renegotiation led by manager Neil Reshen gave him unprecedented creative control at RCA, Jennings chose his own songs, used his own touring band, and released eight studio albums in eight years. The run produced his first Gold album (Dreaming My Dreams), his biggest crossover hit (“Luckenbach, Texas”), and, with Ol’ Waylon, the first platinum album by a solo country artist.

What is the significance of “Wanted! The Outlaws”?

Released in January 1976 and featuring Jennings, Willie Nelson, Tompall Glaser, and Jessi Colter, it became the first country album certified platinum by the RIAA. It also won the 1976 CMA Album of the Year award.

How did Waylon Jennings get creative control away from RCA?

In 1972, while hospitalized with hepatitis, Jennings hired manager Neil Reshen, who rejected RCA’s standard contract renewal and negotiated a new deal with a $75,000 advance and real artistic control—letting Jennings pick his own songs and use his own band, rights he hadn’t had under his prior RCA contract.

Is the Vinyl Me, Please Waylon Jennings box set still available?

It was a limited first edition of 1,000 copies released in November 2023 and sold through Vinyl Me, Please, which lists the set as a members-only title. New stock is not guaranteed; copies do appear on the secondary market through sites like Discogs and eBay.

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