Willie Nelson's All-Time Biggest Gambles

While Willie Nelson is a legendary artist from Texas (and we certainly love that fact), he's long since transcended simple regional borders. It's almost too limiting to even refer to him as an American icon, though he is obviously that without question. The man is a survivor, an activist and practical spiritual guru, aside from being as genius of a musician as there is roaming the highways and dirt roads of the touring trail these days.

Indeed, the past couple of decades have seen Nelson calm down in terms of his non-musical exploits. Fewer movie roles and, aside from a minor drug-bust on the border a few years ago, a seemingly calm family and personal life have made some folks forget that Willie was once as wild as they got from the late 1950s all the way through the '80s. His inclusion in the group of so-called "Outlaws" was warranted for decisions and actions made both in the studio and at home.

For better or worse, Willie has gone with his gut and gone where his beloved sweet smoke has taken him. There's little argument to be made that some of the moves he's made over the years have been wild head-scratchers. But other gambles have turned into massive victories as well. With Nelson's annual Fourth of July Picnic going down Friday at Billy Bob's Texas in Fort Worth, what better time than now is there to look back at some of the craziest examples of Willie Being Willie.

5. He Sold the Rights to "Family Bible" for $50.00 In the very late 1950s, Nelson was broke and had a family to support. He was only beginning to showcase his ability to write future classic tunes, but he wasn't seeing any money from sheer potential. Willie was confident more great songs were on their way from his guitar, so armed with the surefire hit and now-gospel classic, "Family Bible," Nelson asked only $50.00 for the complete rights to the song. In 1960, the song hit the charts with a bang for Claude Gray and has since become recognized as one of the great gospel tunes of the past century. He did what he had to do in that moment to provide for his family with very little future calculation involved. As a result, Nelson's rep as a keen writer began to grow larger and what might've seemed like a gamble at the time ended up paying off rather well.

4. Willie Goes Reggae From a purely logical perspective, Nelson's 2005 album, Countryman, his first full-length foray into a style he has loved for years, had no business being recorded let alone released as a proper Willie album. But from a "Hey, this is Willie we're talking about" perspective, it's shocking this album wasn't made way before it was. Willie has always been open to seemingly insane musical concepts, so why not? It's a noble attempt, which few will argue, but a Willie album with a marijuana leaf on its cover and half-hearted versions of songs old and new isn't worth the time of a reggae or country fan. Only the most stoned of Willie backers defend this album, and once the fog clears, even they probably reach for Phases and Stages and chuckle at the CD cover that lies next to the torn, empty Ho-Ho wrapper on their floor. Screw it; it's Willie doing what he wanted to, so it's cooler than it should've ever been.

3. Willie Nelson, the Latin Lover and Pop Crooner In another instance of what seemed like an odd roll of the dice, yet proved to be anything but, Willie shared a studio with global superstar Julio Iglesias in 1984 for "To All the Girls I've Loved Before." Of course, Willie had convincingly displayed his more polished chops with 1979's genre-bending classic Stardust. But this was a different thing, as Willie, no stranger to duets, had yet to garner the reputation he has now as someone who'll sing with just about anyone. (See also: Rob Thomas and Kid Rock) Not only did the song help turn Willie into a bona fide crossover star, but his music then spread around the world faster than it had ever done prior. The duo even won the CMA award for Duo of the Year, which still makes the least likely (though maybe one of the greatest) pairings to win that award ever.

2. Burn the House, But Not the Pot. As the '60s rolled into the '70s, Willie was making things highly difficult for himself with the ladies. Wives, co-stars and club employees all loved Willie's laid-back charm as much as his fans did. In 1970, just before his revolutionary (and permanent) move back to Texas, Willie was writing some of the best songs he would ever pen. He also found himself in some of the hottest water he would ever wade into. Then things became really hot at home -- literally. Upon realizing that his Tennessee home was engulfed in a blaze that would destroy it, Willie ran into the fiery house to save, you guessed it, his beloved stash. Nelson gave People magazine an honest account of his thoughts during the fire when he said, in a 1980 interview, "I had this pound of Colombian grass inside. I wasn't being brave running in there to get my dope; I was trying to keep the firemen from finding it and turning me over to the police."

1. Willie Becomes The Red Headed Stranger and Country Savior In 1975, Willie successfully turned his rebellion against the Nashville system and burgeoning orchestral Countrypolitan sound by convincing Columbia Records to grant him full creative control over the recording of his first album with the storied label. In an ingenious move, Nelson counter-programmed the slick, over-produced product that had long dominated the Country charts with his own taste for sparse, almost jazzy arrangements and poetic storytelling. Recorded in Garland on a fraction of the budget he was allowed at what was then named Autumn Sound Studios (which now operates as Audio Dallas Recording Studio), Nelson employed an intimate, raw-boned production and but a small handful of instrumentation to craft the masterful, iconic concept album of a murderous preacher on the run. Though Nelson had been doing really well for himself at that time, it's not a stretch to say that if this record hadn't been a smash hit, he could've lost most, if not all, of the good grace he had built with the suits in Nashville, perhaps bringing an end to Nelson the Artist as we know and love him now. The Red Headed Stranger not only became one of the biggest commercial successes in country music, but it's since become universally recognized as a quintessential document in the country music canon.

Willie Nelson performs Friday at the annual Willie Nelson's Fouth of July Picnic at Billy Bob's Texas in Fort Worth. Tickets $40-$60 through

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Kelly Dearmore