As established in previous parts of this series, Willie Nelson was on an artistic hot streak throughout the ‘70s and ‘80s, but, as evidenced by his first Fourth of July Picnic, he was no businessman.
And despite being king of the world, financial troubles were just around the corner for him. During one summer in the late ‘70s, his manager, Neil Reshen, mailed a package of cocaine that was intercepted by the Drug Enforcement Agency on the way to Waylon Jennings in Nashville; Reshen’s assistant took the fall for the incident. Then, Nelson discovered Reshen hadn’t been paying his taxes, which meant Nelson owed the Internal Revenue Service a large sum of money.
This episode would unfold in a number of ways throughout the ‘90s, but it doesn’t tell the complete picture of Nelson’s business-minded endeavors. In 1985, for example, Nelson, alongside John Mellencamp and Neil Young, organized Farm Aid, a full-scale festival aimed at supporting farmers, who were suffering from rising mortgage interest rates and crop prices. In Nelson’s spirit, the festival over the years has included acts as wide-ranging as Tanya Tucker and B.B. King to the Beach Boys and Guns N’ Roses, and has since became an annual tradition, nonprofit organization, and a helpline.
The only problem? Nelson never knew when to say “no.” In the late ‘80s, between his acting contributions, involvement in the Highwaymen collective, organization of festivals, another divorce, and, of course, his music career, Nelson had stretched himself thin. He notched another No. 1 single in “Nothing I Can Do About It Now,” but it was his last one for over a decade, and he cancelled his Fourth of July picnic, which wouldn’t return until the mid-’90s.
Oh, and the tax issues. Reshen’s financial troubles and neglect led to the IRS calling on Nelson in 1980 for over $2 million in unpaid back taxes. After trying to fix it through bunk offshore investments, Nelson ended up owing another $2 million. By 1988, the number grew to $30 million. In 1990, the IRS seized all of his assets, and Nelson, in typical fashion, took the fall with grace. He sold off his song catalog for $2.3 million and released The IRS Tapes: Who’ll Buy My Memories?, a double album containing unreleased tracks from the seized masters. He also organized a fundraiser, only to wear a t-shirt on television to promote it that had the wrong phone number printed on it.
The events that transpired are perhaps summed up best in Bruce Robison’s “What Would Willie Do,” recorded by Gary Allan in 2001 for his Alright Guy album. Like that song, this story has a happy ending. Nelson may have been a lousy businessman, but his generosity throughout the years saved him when the IRS auctioned off his possessions. One friend purcashed his golf course and recording studio, while a lawyer for the American Agriculture Movement bought back Nelson’s Luck Ranch, his 700-acre ranch in Spicewood, Texas, as a thank-you for Farm Aid.
So, what did Willie do? He played a bunch of shows to make up the cash, but there was a long climb back to the top. In 1991, Nelson’s son, Billy, committed suicide and it wouldn’t be until the mid-’90s that Nelson would truly be back in true form. After switching labels, he released 1996’s Spirit, recorded with sister Bobbie on piano, and 1998’s Teatro. Sales had decreased from the Red Headed Stranger days, though, but it didn’t matter. Nelson was entering a new period of his life as a legacy act. In 1993, he was inducted into the Country Music Hall of Fame. One decade later, he teamed up with Toby Keith for “Beer For My Horses,” giving him his first No. 1 hit in nearly 15 years and making him, at age 70, the oldest singer to ever top the country charts. His 2002 hit duet with Lee Ann Womack, “Mendocino County Line,” was the CMA Vocal Event of the Year and won a Grammy award for Best Country Vocal Collaboration.
Nelson, then, was somewhat back on top of the world, but the same couldn’t be said for some of his closest pals. In 2002, after a battle with diabetes that also included heart surgeries and emphysema, Waylon Jennings passed away in February at the age of 64. Both June Carter and Johnny Cash would join him the next year, in 2003. So, too, would Ray Charles, less than a year later. Nelson faced his own struggles, including a bout of carpal tunnel syndrome in 2004 and a bout of emphysema that forced him to cancel several shows in 2012. Of course, that wasn’t going to stop Nelson. Before the COVID-19 pandemic, Nelson played over 150 shows a year, and continued to operate his Fourth of July picnics and Farm Aid festivals.
On the music front, Nelson cut a reggae album, bounced back with 2002’s The Great Divide and 2005’s Countryman, collaborated with Merle Haggard and Ray Price for Last of the Breed, which provided a slight commercial comeback for all involved, by climbing to No. 7 on the country chart. More comebacks for Nelson specifically followed, including 2010’s top five release Country Music and 2014’s Band of Brothers, which became his first No. 1 country album since The Promiseland in 1986. He had also signed a new record deal with Legacy Recordings that allowed him to explore his artistic muse without being beholden to commercial expectations. Nelson used that freedom to record several collaborative projects in the early 2010s, including To All the Girls …, a callback to his Julio Iglesias collaboration aimed at spotlighting women in country music, from legends like Dolly Parton and Loretta Lynn to modern day icons like Brandi Carlile and Alison Krauss.
But just as the early 2000s had set a somber tone for Nelson’s inner circle, so, too, did the early-to-mid 2010s. In 2013, Ray Price, in many ways Nelson’s vocal opposite but spiritual brother, passed away. In 2015, Nelson and Merle Haggard teamed up for Django and Jimmie, a tribute to Django Reinhadrt and Jimmie Rodgers that, despite the title, was comprised of original material, including a tribute to Johnny Cash in “Missing Ol’ Johnny Cash” that featured Bobby Bare. The album was another No. 1 hit for Nelson, and a final one for Haggard, who passed away in April of 2016. Suddenly, mortality hit harder for Nelson. He dedicated “He Won’t Ever Be Gone” to Haggard, a song featured on 2017’s God’s Problem Child that was seen as one of Nelson’s heaviest releases in years. Of course, the very next year’s Last Man Standing took the opposite approach, by approaching mortality with humor, wit, and charm. “I don’t want to be the last man standing, but wait a minute maybe I do.”
Indeed, it’s that optimism that’s fueled a career that speaks for itself and with plenty of stories to tell. Instead of slowing down, Nelson rolls on, releasing new music regularly every year and balancing multiple other projects that range from animal welfare to disaster relief, bio-fuel development, and his various festivals, as only he can do. And rather than call this the end of the story, let’s just call it the stopping point for a chapter that remains unfinished.