Track 13 from Red Headed Stranger (1975)
Track 14 from Stardust (1978)
Track 15 from Always On My Mind (1982)

Track 16 from Me And Paul (1985)
Track 17 from A Horse Called Music (1989)
Track 18 from The IRS Tapes: Who'll Buy My Memories? (1991)
Track 19 from Across The Borderline (1993)
Track 20 from Spirit (1996)
Track 21 from Teatro (1998)

Track 22 from Rainbow Connection (2001)
Track 23 from It Always Will Be (2004)

Track 24 from American Classic (2009)
Track 25 from Band Of Brothers (2014)
Track 26 from Ride Me Back Home (2019)

On Willie's 87th birthday in April, Texas Monthly published a giant comprehensive ranking of all 143 albums he's ever released. And I've enjoyed kind of using that as a guide as I went through some of the dozens of albums I hadn't heard before -- it's kind of wonderful to be able to put on a different album by the same artist almost every day and never come anywhere close to running out of new stuff to check out. I focused on just the half of those that were solo studio albums, but in 80 minutes I couldn't even cover half of those. But with songs from 26 albums over the course 57 years, this is by far the most far-reaching playlist I've ever made in these series (the previous records were the John Prine playlist, which spanned 47 years, and the Aretha Franklin playlist, which covered 22 albums). And I wanted to really spread out the selections, so you get music from every era, there's no gap of more than 5 years between tracks here. 

Willie Nelson released his first album a few months after Bob Dylan released his, so they're right there neck and neck as arguably the two longest-running active recording artists in American music -- and prolific as Dylan is, Willie Nelson has had a much more relentless recording schedule, particularly in recent decades. 1992 was just about the only year since 1964 that he didn't release an album, and a lot of those years he released two or three or even four albums. He went through patches of writing less and focusing on recording covers and/or revisiting his earlier compositions, but still stacked up an incredible songbook. Willie wrote or co-wrote 18 of these songs, so the other 8 still give a decent span of his work as an interpreter of other people's songs.

Some songs, like "Darkness On The Face Of The Earth," Willie Nelson recorded over and over, a couple times in the '60s and then again in the '90s. And sometimes he'd record an incredible song once on a low-selling album and then never again, like "Pins And Needles (In My Heart)," which I've been absolutely obsessed with ever since I heard it. "Buddy" is Ron Swanson's favorite song on Parks & Recreation, and "Wonderful Future" is one of a handful of Nelson songs featured in the movie Our Idiot Brother, where Paul Rudd plays a character who names his dog Willie Nelson. Both of those songs are non-singles from fairly obscure albums from before Nelson's commercial breakthrough, and both excellent songs, so I have to conclude that the comedy professionals that chose those songs are true blue Willie Nelson fans. 

There were only a handful of new Willie Nelson compositions on the dozen albums he released from 1977 to 1982, his commercial peak thanks to huge records like Stardust and Always On My Mind. But even when he's singing standards, Willie Nelson went against the grain and did things his way -- almost all his most successful albums from the first half of his career have a backstory about how hard he had to fight just to get it made the way he wanted. In 1984, Nelson recorded 25 of the songs he wrote in the '60s and '70s as beautifully simple voice-and-guitar solo performances, and the master tapes were taken by the IRS when his assets were seized in the early '90s. Nelson negotiated releasing the album as a fundraiser to pay his back taxes, and The IRS Tapes: Who'll Buy My Memories? was a brilliant publicity stunt that raised millions and got his life back on track. But it's also a really affecting record that showed Willie to be the best curator of his own songs. You expect a song called "Country Willie," first recorded in 1965, to be a celebratory theme song, but it's a poignant and sad little tune, rendered even more beautifully on The IRS Tapes than the original. 

Willie Nelson kicked off his late period revival with 1993's Across The Borderline, a Don Was-produced album with stripped down production and covers of songs by non-country artists like Paul Simon and Peter Gabriel -- in a way it was ahead of the curve, since it was released a year before the first of Johnny Cash's celebrated albums with Rick Rubin. It features "Heartland," which Willie Nelson and Bob Dylan co-wrote and sang together (Dylan has also covered one of my favorite Shotgun Willie tracks, "Sad Songs And Waltzes," in concert). But Nelson also followed his peers at other times -- he made Teatro with Daniel Lanois and Emmylou Harris, on the heels of their success with Harris's Wrecking Ball album. But it never really felt like Willie Nelson was chasing a comeback or an award -- he'd make a great record, and then gather up another producer and another set of songs and do it all again 4-12 months later. I was pretty happy to find that he had covered one of my favorite Tom Waits ballads, "Picture In A Frame." My last album had a song that I'd started out going for a Tom Waits vibe and then by the time I'd finished it I was going for more of a Willie Nelson vibe.