By Kelly Dearmore

Few modern musicians have been as prolific as Willie Nelson. Since debuting with  … And Then I Wrote nearly 60 years ago, an average of more than two records per year have donned his iconic name. That large quantity, while admirable, isn’t what’s most impressive about the Willie discography. His consistently high level of quality is what’s truly astonishing. 

If you were keen to cull a collection of Nelson’s greatest musical achievements, cherry-picking tunes and records from his superb run in the ‘70s and ‘80s would be the sensible thing to do. But what’s the fun in that? Each of the seven decades Nelson has released music in have produced standout material, including the 2020s - this year’s First Rose of Spring has to be one of the greatest albums by an 87-year-old ever. Here are Bandbox’s picks for the best of each decade of the Red Headed Stranger.

1960s …And Then I Wrote (1962) 

Nelson had no problem making a name for himself as a songwriting genius, nor did he waste any time in establishing himself as a guy always looking for a quick buck. Five years prior to the release of his debut, Nelson infamously sold the song “Family Bible” for $50, only to see it become a massive hit for Claude Gray in 1960. From there he landed a writing deal, which yielded Faron Young’s “Hello Walls” and Patsy Cline’s “Crazy,” both of which were immediate smashes and have become classics of the country music canon. …And Then I Wrote offers Nelson’s versions of those timeless tunes, as well as other notable originals, such as “Funny How Times Slips Away.”

1970s Red Headed Stranger (1975) 

The ‘70s are, without question, the most difficult decade of Nelson’s career to pick a best album for. Anyone holding up Phases and Stages, Shotgun Willie, Yesterday’s Wine or Stardust as his best ‘70s LP could make a convincing case. One argument that can’t really be made for those records, however, is that none of them helped morph Nelson from country singer to music superstar the way the sparsely-produced murder concept album Red Headed Stranger did. For just $4,000 in studio costs, Nelson keyed in on a stark, somber sound that couldn’t have been less commercial at the time, even though it went on to sell over two million copies. 

1980s Always on My Mind (1982) 

Nelson’s 27th studio LP is most famous for its grand title track, but there’s so much more to appreciate here. Covers of Simon and Garfunkel’s “Bridge Over Troubled Water” and soul gem “Do Right Woman, Do Right Man,” would have been ill-advised material for most country stars of the day, but Willie wasn’t and isn’t your typical country star. As a whole, Always on My Mind is yet another example of how Nelson can take decidedly unconventional material and filter it through his own unique lens, for a look and feel that isn’t country music as much as it is Willie Nelson music. 

1990s Spirit (1996) 

If we’re being honest, the ‘90s began Willie’s feast-or-famine era of albums. There’s plenty of greatness to be heard, but albums that feel a bit more disposable seem to pop up with more regularity than in the decades before. With that said, the prime material from last millennium’s swan song matches up beautifully with the revered works of his career’s first three decades. 1996’s Spirit served as a brilliant reminder than Nelson needs little more than the most basic of instrumental augmentation to send the listener into new realms. Whereas in the past Nelson had employed his love of jazz to spruce up his country leanings, Spirit proffers a Spanish flourish that feels native to American roots music. “Too Sick to Pray” is a gorgeous, solemn heartbreak of a tune that deserves so much more praise. 

2000s You Don’t Know Me: The Songs of Cindy Walker (2006) 

Much of the aughts were spent with Willie residing on the Lost Highway record label, alongside Americana stars like Lucinda Williams and Ryan Adams. For the most part, Nelson’s albums from this decade align with that musical vision. But in 2006, just a few days before legendary songwriter Cindy Walker’s death, Nelson released an album packed with his own takes of her best tunes. As on brand as any other Nelson album, Willie shines a loving light on some of the greatest compositions from country’s swingin’ era, like “Bubbles in My Beer” and “Don’t Be Ashamed of Your Age.”

2010s God’s Problem Child (2017) 

Over the past decade, Nelson has forged an impactful artistic relationship with Nashville super producer Buddy Cannon. Some of the albums Cannon and Nelson have teamed up on have come out a tad too polished, but God’s Problem Child is a winner thanks to Willie’s vocal A-game. It’s no secret that, in concert, his “singing” these days amounts to little more than talking into the microphone. Apparently, he saves his breath for truly moving studio performances, as evidenced on this stirring LP. Nelson’s writing also continues to shine on songs like “Delete and Fast Forward” and “Still Not Dead,” giving an insightful peek into his own mortality and that of those around him. 


Kelly Dearmore is a music writer based in Dallas. He has written for The Dallas Morning News, Houston Press and Lone Star Music.