At 93, Willie Nelson has spent decades as an outlaw country music icon, known for his love of marijuana and his anti-establishmentarian views. So it may surprise you – and it surprised me – to learn that Willie once tried to live a “healthy” lifestyle, attempting a 10-day juice cleanse and running two miles a day. Of course in classic Willie fashion, the running was in cowboy boots, and the juice cleanse was described simply as “horrible”.

“In the early Eighties, [Merle Haggard] came to stay with me in Texas to record. We were living pretty hard back then, but we’d also try to be a little healthy. We used to go jogging a lot. We’d burn one down and run two miles in cowboy boots,” Willie shared with Rolling Stone in 2016.

“In Texas, we went on a 10-day cayenne-pepper juice cleanse. It was horrible. One day after we’d been up all night, Merle went to the condo to get some rest. Around 4 a.m., we woke him up to sing his part on “Pancho and Lefty.”  He sang it half in his sleep, but Hag sings pretty good in his sleep.”

Willie, however, has kept himself healthy with his love of the martial arts; he holds a fifth degree black belt in the Korean martial art of Gongkwon Yusul, plus a second-degree black belt in taekwondo.

Willie and Merle were friends for over five decades after they met in the early 1960s in Nashville, when Merle was invited to a poker game at Willie’s house by a mutual friend. As well as getting married young and both hopping trains as young men, they bonded over their love of music, and released several projects together over the years, including 1983’s Pancho and Lefty, Seashores of Old Mexico in 1987, Last of the Breed also in 1987, and Django and Jimmie in 2015, a year before Merle’s death.

Now, 10 years from Merle’s passing, Willie will release his 78th career solo studio album, a tribute album to Merle’s work. Workin’ Man: Willie Sings Merle will drop on November 7, and features 11 country classics penned by Merle.

1. Songwriting star

Willie Nelson wrote his first song when he was seven years old and joined his first band aged ten.

2.  Abandoned by parents

Willie and his brother, Bobbie Nelson, were given up by their mother and father, and their grandparents ended up raising them.

3. He has two birthday

Willie was born on April 29, 1933; however, he was born close to midnight, meaning the county clerk recorded his birthday as April 30. So he now celebrates on both days!

4. Hospital bill affair

His ex-wife, Shirley Collie, learned Willie was having a decades-long affair when she discovered a hospital bill revealing his mistress had given birth to a baby girl.

5. IRS tensions

In 1990, the IRS claimed Willie owed $32 million in income taxes and seized most of his assets. He released an album called The IRS Tapes: Who Will Buy My Memories? and the sales contributed to paying off his debt.

Willie himself has been performing for 63 years, after releasing his debut album in 1962.  In 1972, the singer decided to “retire” from recording music after a string of his albums failed to make a commercial impact. He bought out his contract and moved to Austin, where he discovered a renewed perspective and returned to the studio.

His 1973 record Shotgun Willie received critical acclaim and became one of the pioneers of the “outlaw country” movement. Two years later, his 1975 LP Red Headed Stranger became his first crossover hit, solidifying his place in the mainstream and is now considered his masterpiece.

Decades later, Willie is still performing, and he shared in 2025 that there was only one way he would retire, if he lost his beloved guitar Trigger.

Trigger is a Martin N-20 nylon-string classical acoustic guitar, which he purchased in 1969, and has become synonymous with Willie’s sound, and is now a key part of his legacy.

“One of the secrets to my sound is almost beyond explanation,”  he wrote in his book The Tao of Willie: A Guide to Happiness in Your Heart. “My battered old Martin guitar, Trigger, has the greatest tone I’ve ever heard from a guitar… If I picked up the finest guitar made this year and tried to play my solos exactly the way you heard them on the radio or even at last night’s show, I’d always be a copy of myself and we’d all end up bored.”