Look, I realize this is absolutely insane. How am I going to write a piece on a legend who has been a recording artist for 64 years? I’m going to leave a lot of shit out, that’s how. You already know who Willie Nelson is, whether you’ve watched or listened to his movies and music, or whether you’ve bought his weed or his biodiesel. Even if none of those apply, you know him as a defender of the American farm with or at the very least as a punchline for his IRS troubles. I’d like to point out that when the IRS auctioned off all of his property and possessions, his friends bought all of his stuff, and gave it back to him. You have to be a real awesome person for the world at large to decide that no one is going to screw you over, and everyone is going to pitch in and help you.

I’m just going to hit some highlights here, some of my favorites, and it’s all for the purpose of the final entry. I wanted to post something special for Election Day in the United States, and I couldn’t think of anyone better to celebrate, even if Nelson deserves more attention and space than I can give him… he gets that everywhere all over the globe. I never wanted to do anyone too popular here, but you’ll see why I did this at the end. So, enough of that, here we go!

Naked Willie (2009)

Willie Nelson started playing guitar at 5, and started writing his own songs at 7. Makes you feel like a lazy sack of crap, doesn’t it? In his time, he has slept in a ditch and rode the rails (unlike that fraud Boxcar Willie) attempting to make his way to Portland, Oregon (after failing in San Francisco). Eventually, he got a job as a disk jockey, like many aspiring musicians did back before Clear Channel replaced everyone on the radio with Replicants. He recorded his first single in 1956, but it failed miserably. So, he did what anyone else would do, he moved to Fort Worth Texas and sold bibles and vacuum cleaners door to door, eventually making management with Encyclopedia Americana.

In an attempt to sell his songs, he was given a job to sing six nights a week at the Esquire Ballroom. He did end up selling two of his most famous songs, “Family Bible” which became a hit for Claude Gray in 1960, and “Night Life” which became a hit for Ray Price in 1963. Nelson moved to Nashville in 1960, but nothing really happened for him until he joined Price’s band as a bass player (when previous bassist Johnny Paycheck quit). He did sign with Liberty Records, and did have a top ten hit in 1962, but his contract with Liberty went nowhere. He resumed writing songs for other artists, most famously “Crazy” by Patsy Cline.

In 1964 on the strength of his songwriting, Nelson moved to RCA Victor, which is where he met Waylon Jennings (more on that later). However, the Nashville music machine layered a bunch of strings on top of Nelson’s songs because back then singers had no input on arrangements, everything had to be slick. So how does this bring us to 2009?

Longtime member of Nelson’s band Mickey Raphael, took the masters and stripped them of all the extras, in the style of Beatles’ Let It Be… Naked. The result is a collection of music that is bare and much more direct.

Shotgun Willie (1973)

After a series of failures on RCA, Nelson quit the music business and retreated to his farm (but RCA kept putting out albums into 1972, but RCA refused to work with Nelson unless he reupped his contract earlier than anticipated, but he was losing money on every record he recorded with them). While working on his farm, spirits crushed and broken, he started getting drunken, rambling calls from Jennings telling him he needed to come down to Austin and see what was happening.

Nelson relented, and what he saw would set the course for his career. The hippie music scene in Austin was mixing with country and western swing and coming up with “Outlaw Country”. Part country, part rock, with a focus on storytelling would save Nelson’s career. Nelson and his band, “The Family”, signed with Columbia Records and collaborated with Jennings and his future wife Jessi Colter, then released Shotgun Willie. It is considered one of the very first outlaw country records.

Red Headed Stranger (1975)

Nelson’s Columbia contract stipulated complete creative control. When presented with the concept album Red Headed Stranger, Columbia balked, but Nelson forced them to put it out. Can you imagine an artist today forcing a label to release anything? The album was a smash hit, and in 1986 a companion film, which had been in gestation forever, was finally released. It… was not a smash.

Willie and Family Live (1978)

Recorded live in April 1978 at Harrah’s in Lake Tahoe, and released in November 1978, Willie and Family Live was initially a double LP. It was reissued in 2003 as a double CD clicking in at ninety-four minutes. Despite uneven reviews, most of this collection is a barn burner. It’s hit after hit after hit. The only part of it that I don’t care for is the fifteen minute “Red Headed Stranger Medley”, because it kind of just derails the setlist. Emmylou Harris provides background vocals, and Johnny Paycheck appears to play his hit “Take This Job and Shove it.”

Highwayman (1985)

For Nelson, the 70s were filled with concept albums (Phases and Stages), tribute albums (To Lefty From Willie, Sings Kristofferson), cover albums (Stardust) gospel albums (The Troublemaker), and a duet album with Waylon Jennings (Waylon & Willie, highly recommended). Into the 80’s, Nelson scored some hits with “Always On My Mind”, recorded first by BJ McCall, but made popular by Elvis Presley ten years earlier, and a duet with Julio Iglesias, “To All the Girls I’ve Loved Before”… which became Nelson’s biggest European hit and Iglesias’ biggest US hit.

Also, Nelson’s manager continually filed tax extensions throughout the 70s with the IRS, but never actually paid them. Nelson released Who’ll Buy My Memories? Vol. 1 (The IRS Tapes) as a fundraiser. It’s out of print and fetches a pretty penny.

But my money is on 1985’s Highwayman, which was also the name of the band until they continued making records and became The Highwaymen. The group was Nelson, Jennings, Johnny Cash, and Kris Kristofferson. Kristofferson was emerging as a “progressive” country songwriter (despite being a published songwriter since 1966), and the other three had covered his songs before. Cash had a holiday television special every year, and he was responsible for bringing everyone together. They all got along famously, and said “hey, we should do an album!” Usually, that never happens, but this time, they put it together. The album suffers a little from the trappings of the 80’s production, but it’s still fun.

Across the Borderline (1993) / Spirit (1996) / Teatro (1998)

Once the 90s hit, Nelson has a bit of a career resurgence. Across the Borderline is a mostly cover album, with songs by Lyle Lovett, Paul Simon, Bob Dylan, and Peter Gabriel (!). It also has tons of friends, like Dylan, Simon, Sinead O’Connor, Bonnie Raitt, Kristofferson, Don Was, and many, many more. But my favorite is Nelson’s original “Still Is Still Moving To Me.”

in 1996, Nelson released a very stripped-down album based on classical and Spanish guitar, titled Spirit. It is just Nelson, his sister Bobbie on piano, a fiddle, and an additional guitar (both provided by Family band members).

Teaming up with famed U2 producer Daniel Lanois, Nelson recorded 1998’s Teatro was recorded in an empty theater of the same name. The album has a drum heavy sound, and is very sparse. I don’t know that I necessarily like it, but it’s definitely different.

Milk Cow Blues (2000) / Two Men with the Blues [with Wynton Marsalis] (2008)

Nelson spends some time exploring the blues in the 2000s, with Milk Cow Blues which is a duet album of mostly covers (but with five Nelson standards). Nelson duets with Francine Reed, Keb Mo, Dr. John, Johnny Lang, and BB King.

In 2007, Nelson performed a concert with Wynton Marsalis at the Lincoln Center and that was recorded for Two Men with the Blues. The band is Marsalis’ band, with the addition of Mickey Raphael on harmonica.

Countryman (2005) / Willie and the Wheel [with Asleep at the Wheel] (2009)

The decade had continual exploration from Nelson (he also did have a slate of regular country albums as well. Well, the last two decades, I guess. Countryman, Nelson’s reggae album, was recorded originally recorded 1995-96, and finally finished in 2004. My favorite is the cover of Cash’s “Worried Man”, which is also on the Nelson/Cash VH1 Storytellers from 1998, which is fucking great, but I’m trying to succinct.

While going forward, Nelson also went back… way back. Nelson teamed up with West Virginia Western swing group Asleep at the Wheel for Willie and the Wheel. The album was nominated for Best Americana Album at the Grammy Awards. Today, I learned there was a category for “Best Americana Album”. There’s not a lot to say about the album, except that it’s really fun, and listening to it makes me want to go to a small-town festival, eat a funnel cake, and sniff a bunch of manure. Well, maybe not the last thing.

Also, in 2009, Nelson released Lost Highway, which received less than stellar reviews. It’s important because it includes “Cowboys Are Frequently, Secretly Fond of Each Other”. Nelson had a different song included on the soundtrack to Brokeback Mountain, and actually released “Cowboys” as a stand alone single in 2006.

The song was written by Latin country musician (and author and musicologist) Ned Sublette back in 1981, when he lived near a gay cowboy bar in Manhattan. Although Sublette recorded his version in 1982, he states that he wrote it with Nelson’s voice in mind. “I was at the beginning of my songwriting career … and used to like writing songs for my favorite voices. I’ve been a Willie fan since the ’60s.”

In Nelson’s prepared statement, he stated, “The song’s been in the closet for 20 years. The timing’s right for it to come out. I’m just opening the door.” David Anderson, Nelson’s manager and friend for 30 years, came out in 2004, and encouraged Nelson to record the song. “This song obviously has special meaning to me in more ways than one. I want people to know more than anything—gay, straight, whatever—just how cool Willie is and … his way of thinking, his tolerance, everything about him.”

Reception was mixed… is probably the best way to put it, but Nelson said that he has heard very little negativity about the song. “Every now and then somebody might get a little offended. It’s got bad language in it, so I just don’t do it in my shows. Anybody wants to hear it can hear it on iTunes. But you know people are listenin’ to it, likin’ it. Every now and then somebody don’t like it, but that’s okay. Similar to years ago, when the hippie thing come out and I started growin’ my hair and puttin’ the earring in, I got a little flak here and there.” Of course, country fans were pissed off, but who cares about them. Nelson stated that he didn’t think anyone, anywhere would play it anyway, but it did find an audience. When mentioned to Nelson that country stations weren’t playing it, he said, “Oh no, they’re not gonna play it.”

Willie Nelson Sings Gershwin (2016)

I didn’t pay much to Nelson in the 2010’s, through no fault of his, but he put out fifteen albums in the decade. Fifteen, Nermal! I just didn’t have the bandwidth to pay attention. But he did put out a cover album of Gershwin standards, appropriately titled Willie Nelson Sings Gershwin. It features duets with Cyndi Lauper and Sheryl Crow, and won a Grammy Award in 2017.

“Vote ‘Em Out” (2020)

Here it is, the reason I went through all of this. On September 25, 2020, Nelson released his most recent single, “Vote ‘Em Out”. Despite being general enough that it could be applied to any election at any time, a large segment of the fan base was actually enraged at Nelson for being “too political”. Obviously, his plight for preserving he environment, standing for equal rights (I didn’t mention it, but he toured with Charley Pride back in the day, and would refuse to go on when white establishments would try to block Pride from playing), supporting marriage equality, and being vocal about marijuana legalization (he smoked pot on the roof of the White House with Jimmy Carter’s son, for crying out loud!)… all of that went over their heads. Clearly, they have not been paying attention these past 64 years.

So, listen to Willie Nelson. Get your ass up tomorrow, and GO VOTE ‘EM OUT!