Willie Nelson: The Friendliest Outlaw

Born at or around midnight, no one can be too sure if his birthday is on the 29th or 30th, but that doesn’t matter to us. We’re so glad to share the good Earth and the good life with this friendly outlaw. We’re giving a big Happy 93rd Birthday to Mr. Willie Nelson.

Raised in Abbott, Texas by his grandparents, lovingly called Papa and Mama Nelson, Willie and his sister Bobbie were no strangers to good music. Their grandparents taught the two children how to play piano, and they gave Willie his first guitar, purchased from the Sears catalog, at just 6 years old. From then on, Bobbie and Willie could always be found at Sunday Service making music together. Other than music, Willie’s dream was to be a cowboy like Will Rogers and Hopalong Cassidy; as any good Texan boy would. He just needed to figure out how to marry the two dreams.

From the age of 18, Willie worked hard and bounced from music halls to radio stations to the Air Force, finally moving to Nashville in 1960 to kickstart his music career. His homebase, like his fellow songwriters at that time, became Tootsie’s Orchid Lounge, the bar directly behind the Grand Ole Opry. It’s the same bar where he would eventually sign with a Nashville publishing company to write hits, like “Hello Walls,” “Funny How Time Slips Away,” “Pretty Paper,” and, “Crazy.” With all of this newfound success, Willie bought a beautiful ranch in the hills of Tennessee.

Nashville was also the place where Willie would meet his lifelong friend and companion: a Brazilian rosewood, spruce top Martin N-20 guitar, which he eventually named Trigger after Roy Rogers’ horse. Every good cowboy needs a good sidekick, and Willie’s guitar was no different. He loved that guitar so much that when his Tennessee ranch went up in flames, he ran right back into the burning building to save his friend.

With everything gone up in smoke, Willie decided it was time to hit the road and make music his way. So he packed up everyone and everything, and headed back to Texas; Austin to be exact. The cowboy set up shop, signed with RCA, and formed his new backing band called the Family. The lineup included drummer and former criminal Paul English, 21-year-old harmonicist, Mickey Raphael, bassist Bee Spears, guitarist Jody Payne, and piano extraordinaire, his sister, Bobbie Nelson. Willie traveled all over and played with every Nashville musician worth knowing, but all he needed was to go home and make music with his sister, once again. Austin allowed Willie to creatively grow into his own genre, Outlaw Country, and it’s where he started his annual festival: Willie Nelson’s Fourth of July Picnic.

One summer, Willie found out that his manager, Neil Reshen, had not been paying the IRS. Meanwhile, a package with some cocaine traveled from Reshen’s office in New York to his friend, Waylon Jennings, in Nashville, which was followed by the DEA. Jennings was arrested, but the charges were dropped, and Reshen’s assistant, Mark Rothbaum, took the fall. When Willie heard about this, he fired Neil and told the Family he would be hiring Mark as his manager as soon as his jail sentence was served. Once you’re part of Willie’s circle, you’ll always be taken care of.

And Willie kept on giving; he always made sure his people were taken care of. In 1985, Willie’s good friend and Governor of Illinois, Jim Thompson, told him about the farmers that were struggling in his state along with his concerns for their livelihoods. Twenty-two days later, Farm Aid came to fruition with help from Neil Young and John Mellencamp, two of Willie’s good friends.

Willie could make friends anywhere he went. During the third season of SNL, Willie and the Family made their first musical appearance. What a rowdy week that was. Every night after rehearsal, the band would head to the Lone Star Cafe and play deep into the early hours of the morning. They were joined by new friends Bill Murray, Dan Aykroyd, Gilda Radner, and Jim Belushi. Years later, Aykroyd would tell Willie that the Family was the first backup band Blues Brothers ever had.

In 1990, everything came to a head. The IRS seized every asset Willie had and put them up for auction to pay the back taxes he owed. Suddenly, Willie had nothing to give and watched all of his earthly possessions get sold off one by one. The outlaw had nowhere to run. Now was the time for the Family and Willie’s friends to step up and give their pal a hand. The studio and golf course was purchased at a low bid by Willie’s long-time friend, Darrell Royal, the University of Texas football coach. Willie’s home was purchased privately by a group of farmers that benefited from Farm Aid. And when the instruments were up for auction, a bus driver from Florida Coach, the company who built out all of Willie’s tour buses, saved Bobbie’s piano and several other pieces from the studio.

Once a friend of Willie’s, always a friend. But what about Trigger? Ask anybody: the Family, Willie’s lawyer, and friends alike will all tell you they kept Trigger safe during the auctions. No one ever revealed his hiding place. After all that upheaval, Willie and Trigger were reunited, never to part again.