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Larry Shaeffer holding guitar

Larry Shaeffer’s Legacy Part 3: On A Collision Course

by | People

Continuing from Larry Shaeffer’s Legacy Part 2: The Road To Success.

It’s as though one is standing inside his memories while gazing at the walls of his office. Remnants of almost 50 years aboard a metaphorical train that has sped through the years on a mystery track leading him on a journey that most only dream of. As the conductor, this man chose to travel through melodic scenery and the darkest recesses to discover the destinations only available to those who believe in them enough to board a train to nowhere in hopes of finding everywhere. 

Getting Off the Gravy Train

When we left last, Larry Shaeffer had decided it was time to return home to Tulsa after spending several years on the road with Hank Williams Jr., promoting his shows. Now a family man with his wife and one-year-old son Jake, it was time for him to evaluate his priorities. As he would soon discover, acting upon those desires would be much more difficult than he initially believed.

Making Plans for Willie Nelson

Having been in the midst of the fast lane lifestyle since the early 1970s with the sex, drugs, and rock n’ roll associated with that scene, becoming a family man was a lifestyle on the opposite side of the tracks for Larry. Being in the music business had been all he had known since those early days of flipping cars and selling fireworks and t-shirts to make a few bucks. Even with a degree from the University of Tulsa, he still only had his music business experience and the desire to keep the music playing in Oklahoma. Fortunately, he still owned Cain’s Ballroom and had a hefty bank account from his successful promoting ventures. He believed at that point that there would be “no more big money,” but he was okay with that situation.

“One of the reasons I came back to Tulsa was that I thought I had enough money to last forever. I had done very well financially, and I had proven to myself that I could do some bigger things than what I had been doing… but, then I got into a marriage that did not last forever… and it took a lot of money,” Larry said. He also felt that he had not really put the effort into Cain’s that he should have, and it was time to remedy that.

By his admission, his best years were from 1975 to 1995. His focus on Cain’s was paying off, and it became a mecca for live music in Tulsa. Yet, even as a family man, he still could not stop chasing big money and was “scratching and clawing” with the competition to bring in arena shows. His efforts brought Prince, Judas Priest, Tina Turner, Van Halen, Willie Nelson, Kiss, Aerosmith, Metallica, Ozzy Osbourne, and even the great Frank Sinatra, among others in, this attempt and desire to continue growing in the business.

 He was initially happy to be home and enjoying the absence of travel. But in many ways, he was in uncharted territory. He admits loving the lifestyle and the women involved in the music scene as well the wild side of the business. He had never seen himself as married with normal home life, but there he was, just that. His love for his sons and daughters inspired him to learn how to be a good father, but this alone was not enough to keep from dragging the chaos surrounding him into his marriage and home life. It would soon become evident to him that the train was on a collision course. Yet, he still continued gaining steam to feed what he believed to be chasing the American dream.

Obstacles on the Tracks

He admits that the stress of his home life, coupled with the chaos of the business, pushed him further into drugs and alcohol.

Larry Shaeffer with Chuck Berry

“I had been warned that drugs and alcohol don’t mix with money. But I just wasn’t listening. So I made a lot of tactical errors. This is where my demise starts,” Larry said. On a more philosophical note and one of retrospect, he explains that when asked if he would do it over differently, the answer is a resounding YES! Perhaps, the best way to describe his response as it relates to this story is by looking back at the tracks from where a speeding train had just been. Reviewing what had been on the tracks and decimated by its sheer force, the realization that what had been so close was now gone forever in the distance.

Maybe there were regrets. Perhaps even life lessons. Whatever they may have been, it was most certainly a realization that he was destroying what he had hoped to build by returning to Tulsa. There would be other obstacles on the track in the near future, such as a rape accusation and trial before a jury. But those obstacles would be just what he needed to slow down. He would be cleared of the rape charge, but the damage to his reputation and the continuing spiral into drugs and alcohol were almost enough to derail him.

Traveling in the Darkness

“I became my own environment. I woke up in the morning being me and doing the same things I did the day before and hoped that it would work,” Larry said. “I also never thought that the flow of money would quit coming. It was so easy to get. This thought process and substance abuse would usher in consequences detrimental to his promoting enterprise. He admits that there were show settlements he closed while high that were not handled as well as they should have been, and this caused riffs between him and the artists. Many of these would have long-lasting effects.

“The show may have sold out and we all made good money. But I did not make a good impression on the artists I was working with. There were several instances when I nuked myself because of the drugs and alcohol.” Larry said. One example of this behavior was casually offering Garth Brooks’ manager, Bob Doyle, cocaine after a show. Doyle was so insulted that he informed Brooks, who refused to work with Little Wing again. He kept true to his word and has never worked with Larry since.

“Some mistakes you make, you never get through paying for,” Larry said about the Brooks’ incident. He went on to explain that though there were not a large number of those types of mistakes, there were enough to cripple his position in the business. He admits that at the time, he had no idea how much damage to his career he was inflicting upon himself. Interestingly, though, he knew to some degree that he would derail if things didn’t change, but he had no clue how to get off the speeding train or stop it.

Running Off the Rails

During this period, he had been arrested on multiple occasions for what he refers to as alcohol offenses and his party lifestyle. To add some perspective about where he was at this point in his life, it should be noted that it was not ego that had landed Larry into this myriad of issues he was battling. In fact, it was quite the opposite.

Leon Russell

“This level of fatigue had set in and I had managed to keep three balls in the air for many years and I didn’t know how much longer I could do that. I never really thought I was equipped or even qualified to be in the business I was in. I kind of thought I was pulling off a fast one here,” Larry said.

“I also had the false illusion that success was measured by money. I think that is one of the flaws in the American dream…that we all get measured by how much money we make,”. When asked if he had given any thought at this stage of his life as to how much joy and how many memories he had given to music lovers over the years through his efforts, he replied, “absolutely not, I never thought about it.” He felt good about how far he had been able to build Little Wing. But he was oblivious to the simple level of how he had touched so many lives or what he was doing had significant historical value. “I am realizing it now, finally,” he quipped.

Finding the Breaks

“I finally had an epiphany that my values were wrong and had been for decades. I wanted to get away from it,” he said. And the cost of owning such an awakening? Everything I owned. “I had to lose everything! I filed for bankruptcy in 2001 with nothing left. I simply walked away from Cain’s Ballroom. It was not a big sale where I garnered any money. But I finally learned that you can’t buy happiness at all. I had just bought into the idea that too much is never enough,” he said. He went on to say that losing his wife, everything he owned, and almost his children wasn’t enough to wake him up; he was in a lot more trouble than he even thought possible.

But it was enough. For the first time in his adult life, he had become available to those he loved and cared about. In this action rests the wisdom of how important it is to be there for others during this journey through life. It took the battering of obstacles to finally bring the slowing down of the speeding train he was on. He finally understood what was most important in life had been passing him by while roaring that speeding train through the stations without so much as a thought to see what beauty was around him.

“There was a time after the bottom had fallen out that I had no intention of booking even one more show. I just had no direction at that point. I was done with the business, and it was done with me. I was drifting and wondering what my next move was.” Larry said. That next move would come a short time later. An agent in California called him and offered him an opportunity. Knowing that Larry was on a bad roll, he told him point blank that he might as well take the chance since he didn’t have anything else better to do. Larry accepted. He began booking shows for Willie Nelson. Within a year, he made money again and was back on the upswing.

A New Train of Thought

He loved it! There were no more big shows to scramble for and no more drugs and alcohol. He was a “handyman,” as he calls himself, booking shows for Willie Nelson in the “B markets” between his big arena shows in the larger cities. This led him to do the same for others, such as George Jones, Merle Haggard, Ray Price, Don Williams, Gordon Lightfoot, and B.B. King. He had found zeal again and could work with only those he considered professional and easy to work with artists. He had found a niche that worked and made him happy. And he was sober to boot.

Larry Shaeffer with Friends

 For the better part of the last 17 years, Larry has maintained his business with these “elder statesmen” of the music business. In recent years, many of those great performers have passed on, and now nearing 70 years of age, he has no desire to add any more performers. He is happy with promoting shows for Willie Nelson and Gordon Lightfoot while enjoying time with his family, 11 stray dogs, and a 1961 Cadillac which is often as temperamental as any complex artist on a bad day.

The days of the speeding train may be over, but he is more than okay with this fact. He has finally learned that it’s not about how fast he gets somewhere or how many cars he has attached behind him; it’s about enjoying the scenery within this world he has created for himself and countless music fans.

“It’s been one helluva party, hasn’t it?” 

~ Larry Shaeffer
C.L. Harmon

C.L. Harmon


C.L. is an award-winning journalist who spent many years in the newspaper and freelance fields. In addition to holding reporting and editing positions throughout his career, he also owned and operated a newspaper for several years. He was born, raised, and continues to reside in Oklahoma.


  1. dovey a blackwell

    Love the story <3 And Love the man! He is and will always be One of the Best Men I have ever met and I am proud and honored to call him my Friend <3 Thanks for sharing his story with the readers.

    • Spencer Heckathorn

      Thank you for the comment. I also really enjoyed reading this one too and it was very cool to get to meet Mr. Shaeffer and spend some time with him! Great job CL!

  2. Doyal Bryant

    I worked with Larry and Little Wing on several concerts as the promoter of the uptown theater. Your story of Larry is accurate and there was so much to tell. I walked away, would not of made it to age 30 trying to match the lifestyle of Larry.
    Almost died at the boomer theater in Norman producing one of Larry’s shows.
    Thanks for sharing. I have now re-engaged with my music industry contacts. Turns out those 80s rock stars are still touring to a new generation

    • Spencer Heckathorn

      Thank you for the comment. It was really cool to get to hang out with Larry for an afternoon and hear his stories. In the not too distant future, we hope to get the interview with some bonus footage posted on YouTube.

  3. Chris Slagle

    Enjoyed the read.
    I never met the man.
    I did do survey work as a kid for one of Larry’s friends.
    Let’s say the snow fell too much in my life too.
    Glad my old connection thru connection got better!
    Great promoter!!


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Everything in life and in this world moves. It is in some process of change. This is because change is the life blood of existence. And that blood flows continually in a a direction that is rarely the path of least resistance in order to push the most doors of growth open. As a result, it often seems we are not moving forward in life. But in actuality, our flow has just been slowed so we don’t miss seeing the many open doors that life has afforded us. – C.L. Harmon