Willie Nelson's five biggest gambles

Kelly Dearmore
Willie's Gambles Can Turn Into Collectors Items

Aside from being as genius of a musician, Willie Nelson is a survivor, an activist and practical spiritual guru. Over the past couple of decades, his non-musical exploits have calmed considerably. 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. Here are five 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.

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