Billy Bob Whitaker is a bit of an enigmatic character, so piecing together a biography has proven to be a tad difficult to say the least. There are some stories that a few of his associates can vouch for, and others that may solely exist in his own mind. What is known for sure, is that Billy Bob is smart enough to know that adding a bit of legend goes a long way in endearing his character to an audience, especially in the world of country music, where legend can often supersede the music itself.

At least we are confident in knowing the details of his childhood, as this information has been confirmed by various family members. William Robert Whitaker III was born to William and Mary Lynn Whitaker in 1968, on the 11th day of December (or as Billy Bob will say, “the Devil’s birthday”), in the small town of Levant, ME, located just northwest of Bangor. At the time, Bangor and its surrounding areas were known primarily for its lumber & paper industries, as well as housing one of the University of Maine’s many campuses. “There weren’t a lot of ways to escape where I grew up,” says Billy Bob. “Unless you had the money to go to college and get the hell out of town that way, you were pretty much destined for the sawmill. I had 9 brothers and sisters, and we grew up dirt poor, so education was never an option for me. That was okay though because I was never into that liberal crap anyhow. I had to figure another way out.”

Heavily influenced by the burgeoning outlaw country movement of the 1970’s, Billy Bob began playing guitar and writing songs every now and then. He hadn’t taken music too seriously until almost nearly losing his middle finger in a sawing accident. “They were able to reattach my finger and all, but that was the turning point, a sign from God for sure. That’s when I realized I needed to show my precious middle finger to the whole damn world, you best believe that.” Billy Bob left the lumber yard for good and began his life as a vagabond, with just a guitar and a few bucks to his name.

After that, the details get quite fuzzy. Billy Bob was discovered much later in life busking on the streets of Nashville, after what he claims had been over 30 years of hopping trains, drinking, popping uppers, downers, taking the odd job, bouncing from couch to couch when the money was tight, and landing in jail various times over the years. He seemed to embody all the necessary outlaw country tropes, but as far as any specific stories, he’ll usually say something along the lines of “Just listen to the music, my life is in the songs.”

This mysterious nature is what seems to have driven most folks away, but one person that never gave up on him was Don “the Colonel” Walsh, owner and CEO of Freedom First Records. “I just knew that the only way people were going to catch on was if someone invested in him, and I was the man to do that” says Don. “Besides, he claimed he could play a bit of everything, so I figured if he wasn’t pulling my chain, I wouldn’t have to front too much cash. Also, if things didn’t work out, at least I could consider the project as a tax write off.”

Don continues, “The only thing I asked of Billy Bob before I signed him was that he curb his brash sensibilities a bit. I really thought he could make a few viable bids for a pop audience. Next thing I knew, he wrote ‘One Hot Night in Vegas’ and that was it, I knew it could work.”
Indeed, this song was tailor made for the pop charts, but did that mean the story behind the song was exaggerated, all for a shameless bid for the big time? Case in point: Billy Bob claims he would give up being rich and famous to relive a drunken, spur of the moment marriage to a cocktail waitress by an Elvis impersonator. Don laughs, “Yeah, sometimes he has delusions of grandeur. He’s definitely confident his music will be successful, so by the time it’s released, who knows? Maybe he will be rich & famous by the time you hear it?”

Don continues, “But man, one thing I can tell you for sure, is that all the marriages he references in his songs has got to be true. It seems like every half hour or so, some broad calls him up in the studio, yells at him, and he is just agitated as all hell, like the Devil himself had taken hold, and we’ll get a good take.”

Billy Bob adds, “Yeah, the Vegas song was a concession for Don, but it was all true. As a retaliation of sorts, I would write something like ‘Standin’ My Ground’, which is also all true. In fact, there was a verse in that song that Don insisted I remove, about a stint I did in LA for gun charges. Apparently, they have some horribly restrictive concealed carry laws there, so after I brandished my pistol in that bar, I got stuck with all these BS gun charges.” Billy Bob laughs, “When I got out, I knew that’s when I had to high tail it to Arizona, that’s for sure!”

So, if we are left to understand Billy Bob primarily through his songs, “One Hot Night in Vegas” and “Standin’ My Ground” are good examples of what lies ahead for the listener. On one hand, he can display a pop sensibility that could lure in folks of all types. On the other hand, he’ll tell you a story, or describe a particular worldview, that truly plays up that classic, outlaw country typecast. “It’s this duality that I think will resonate with lots of folks, young and old,” says Don “which is such a refreshing contrast to the pretty boy ‘bro country’ BS dominating the charts these days.”

Agreed, or as Billy Bob often says, “and that’s a fact, Jack.”