Please note: This is not an all-encompassing, ultra-complete list of all the hundreds of Willie Nelson best-ofs and reissues ever issued. Discogs can help you with that. I will note, however, that Nelson's catalog is remarkably replete with bazillions of low-rent, sketchy, off-brand, cheapo, dubiously-licensed releases, presumably a result of decades of neglect and disinterest from his old record labels. There is a lot of Willie Nelson "product" out there, much of it thoughtlessly assembled and less worth your attention than the upper-tier reissues. This list below is just my set of recommendations to help cut through the fog, all good stuff, though I'm sure I've missed a few others that would be worth a few spins. Hopefully this will be helpful anyway.
Willie Nelson "Crazy: The Demo Sessions" (Sugar Hill Records, 2003)
Texas "outlaw" singer Willie Nelson has long had an uneasy relationship with Nashville. He first made his mark as a songwriter, providing Patsy Cline with her smash hit, "Crazy," and country crooner Ray Price with the immortal boozer's ballad, "Night Life." As a performer in his own right, though, Nelson's solo career was years in coming -- his now-familiar paper-thin voice and odd, off-beat phrasing were square pegs that round-hole record producers were loathe to take on. These early demo sessions, made between 1960-66, when Nelson was still fresh-faced and eager to please, were made for a publishing house rather than a record label, and lay largely forgotten until 1994, when a faintly-marked reel-to-reel tape was unearthed in a dusty vault somewhere in Music City. They reveal Willie at his rawest and most earnest, and at his darkest and most downcast. Tweaking country music's standard formulas, Nelson gave the characters in his songs more to sing about than just losing a girl and getting drunk: they also became mean drunks, hardcore lost causes who contemplated either murder or suicide, often in the same teary sentence. Some of the demos are just sketches of the songs to come, others are haunting versions of songs that would soften and smooth out over the years. It's all a treasure trove for Nelson fans: well worth picking up!
Willie Nelson "Always On My Mind" (Oh Boy Records, 2000)
This set seems to cover much the same time period as the Crazy collection above, though the liner notes are much more vague and less helpful. It's still Willie, though!
Willie Nelson "The Early Years: The Complete Liberty Recordings Plus More" (Liberty Records, 1994)
This 2-CD box set collects Willie's earliest, string-laden forays into Nashville musicmaking. It seems, sadly, to be out of print, but it's still worth tracking down a copy if you can. Like Willie, most fans don't like what Liberty did with his tunes, but it's worth knowing what he sounded like back when things were getting started.
Willie Nelson "Greatest Hits (And Some That Will Be)" (Columbia Records, 1981) (LP)
A swell, generously-programmed double-LP that covered recordings from 1975-81, along with a few new tracks. Includes some of his best ballads of the era -- "Blue Eyes Crying In The Rain," "Angel Flying Too Close To The Ground," "Georgia On My Mind" -- along with consciously-crafted outlaw anthems such as "My Heroes Have Always Been Cowboys" and "Mammas Don't Let Your Babies Grow Up To Be Cowboys" and singalong hits such as "Whiskey River," "Stay A Little Longer" and "On The Road Again," among others. This is perhaps Willie at his most accessible, not coincidentally overlapping with his hit film, Honeysuckle Rose. Recommended.
Willie Nelson "The Best Of Willie" (RCA, 1982) (LP)
Amid the glut of hastily-packaged, indifferently marketed "product" that flooded the market when people finally realized how famous Willie was, RCA did a particularly poor job curating his work with their label. This brisk budget-line set covers 1965-71, but wisely concentrates on his later stuff, when he emerged as an "outlaw" artist -- songs like "Bloody Mary Morning" and "Yesterday's Wine -- though there are also some less significant tracks such as his version of "Mountain Dew." The suits at the label even decided to chop out a guitar solo from his version of Nilsson's "Everybody's Talkin' At Me," to avoid any danger of percieving Willie Nelson as an actual artist.
Willie Nelson "Half Nelson" (Columbia Records, 1982) (LP)
A cleverly titled though all-too-brief sampling of duets recorded with other artists, including country luminaries such as Merle Haggard, George Jones and Mel Tillis, newcomers like Lacy J. Dalton and several pop crossovers with the likes of Ray Charles, Julio Iglesias and Carlos Santana. It's not quite the free-flowing jam-fest of his later career, but the embrace of diverse styles it there, and the template is set.
Willie Nelson "Beautiful Texas: 1836-1986" (Bear Family Records, 1986) (LP)
The early 'Eighties included a huge flood of off-brand Willie Nelson releases, as everyone and his brother had their hands of Nelson's back catalog. A slightly classier obscurity is this archival gem from the folks at Bear Family, who dipped into his RCA years to put together a Texas-themed set of old tunes, a collection that coincided with the Lone Star State's Hunnerd-and-Fifty-year-entennial.
Willie Nelson "All Time Greatest Hits, Volume One" (RCA Records, 1988) (LP)
This twenty-song set might be RCA's first time really trying to put together a decent Willie Nelson collection, taking advantage of the extended length of the digital era. Also, the song selection is stronger. Again, later years would bring better curation of his career, but this one was actually pretty good.
Willie Nelson "Nite Life -- Greatest Hits And Rare Tracks: 1959-1971" (Rhino Records, 1990)
American major labels were amazingly slow on the uptake when the reissue revolution occurred, with the then-independent Rhino Records taking up most of the slack left after European labels such as Ace and Bear Family took their crack at it. This is one of the first sets trying to approach Willie's early career from a more inquisitive perspective, scratching under the surface to find some early 'Sixties gems while also treating his tenure at RCA as worthy of a little careful thought. It still holds up pretty well.
Willie Nelson "45 Original Tracks: The Complete Liberty Recordings, 1962-1964" (EMI Records, 1990)
This 2-CD European-only collection is a completist gem, gathering all of Willie's dimly-remembered work on the Liberty Records label. This set also includes a half-dozen tracks from his then-wife, Shirley Collie Collins (1931-2010) a country gal who might earn a retrospective of her own someday...
Willie Nelson "The Classic, Unreleased Collection" (Rhino Records, 1993)
(Produced by Willie Nelson & James Austin)
I'm still Rhino, ride or die. This box set gathers many of Willie's rarest recordings, including what are purported to be his first studio tracks, "Lumberjack" and "No Place For Me," as well as his legendary Pamper recordings, made when he was plugging his early work to Nashville's publishing companies. Also gathered are prime tracks from his genre-defying tenure at Atlantic Records, a few solo tracks, some shelved material, and a whole slew of Hank Williams covers. Sweet.
Willie Nelson "The Essential Willie Nelson" (RCA Records, 1995)
Finally: a decent collection of Willie's work on RCA, compiled by the label itself. Easy to find, and certainly worth a spin.
Willie Nelson "Revolutions Of Time...The Journey 1975-1993" (Columba Records, 1995)
Similarly, the folks at Sony were finally catching on to Willie's real significance, compiling a career-spanning, 3-CD box set instead of churning out yet another budget-line "best-of". After the mid-'Nineties, you start having a lot of good choices, but if this was one of the collections you tried, you wouldn't be disappointed.
Willie Nelson "Nashville Was The Roughest..." (Bear Family Records, 1998)
Starting in the late 1970s and early 'Eighties, the fabled West German collector's label Bear Family Records had set the bar for archival reissues and had produced numerous career retrospectives of towering figures in country music history, such as Marty Robbins, Lefty Frizzell, Ernest Tubb, Hank Thompson, Kitty Wells and many others. But what about Willie?? I dunno the story behind why it too so long for Willie Nelson to get the full Bear Family treatment, but I assume the licensing to his back catalog was a real mess, as witnessed by the millions of low-rent, fly-by-night budget-line releases that flooded the world up to this point. Making up for lost time, Bear Family produced this 8-CD monolith, gathering all of Willie's recordings for RCA and Monument Records, between 1964-72. As implied by the box set's title, this was not a period of great personal satisfaction for Willie Nelson, as he pushed against the controlling, often dismissive record company executives who recognized he was bona fide hitmaker as a songwriter, but couldn't figure out how to cram such an idiosyncratic performer into the prefab factory-style assembly-line studio system they'd developed during the so-called "Nashville Sound" years. Although it was his chafing unhappiness during this era that sent Willie back to Texas and into his outlaw persona, there's still plenty of material worth exploring here... and with over 200 tracks total, I do mean "plenty." Also includes a handsome, well-researched 72-page booklet with lots of archival goodies and discographical data. Hardcore fans will want to save up their sheckels for this one.
Willie Nelson "16 Biggest Hits" (Columba Records, 1998)
Yeah, sure. Why not...?
Willie Nelson "The Essential Willie Nelson" (Columba Legacy, 2003)
Willie Nelson "It's Been Rough And Rocky Travelin': The Earliest Willie Nelson, 1954-1963" (Bear Family Records, 2003)
Returning to the hunt, Bear Family followed up with this three-disc, ultra-completist set which delves into prehistoric Willie demos as well as the bulk of his stuff on Liberty Records, including several tracks with Shirley Collins. Lots of multiple, alternate takes, for folks who dig that kind of thing... and a fast-forward button for those who don't.
Willie Nelson "The Complete Atlantic Sessions" (Rhino Records, 2006)
Yes, please.
Willie Nelson "One Hell Of A Ride" (Columbia Legacy, 2008)
A four-disc collection, worthy of our attention.
Willie Nelson "It Will Come To Pass: The Metaphysic Worlds And Poetic Introspections Of Willie Nelson" (Omni Recordings, 2014)
It's true, Willie Nelson has always had an introspective, philosophical side, which the well-curated Australian Omni label zeroes in on with this lofty collection. Good thing Willie sells his own brand of weed, so you can really hear these tracks the way he intended.
Willie Nelson "The Essential Willie Nelson" (Columba Legacy, 2015)
Kinda budget-line-y but Willie's affinity for gospel music is certainly something worth paying attention to. When they assemble the perfect, comprehensive, multi-disc box set, I'll be first in line. But this ain't bad, either.
Hick Music Index
Top photo credit: Rahav Segev, courtesy of Lost Highway Records.