By Judy Hubbard

(LSM Sept/Oct 2011/vol. 4 – Issue 5)

It’s 6:30 a.m. on July 30, 2011, somewhere in Massachusetts, and I can’t sleep, wondering why they call this place the Quality Inn. Maybe in some foreign language “quality” means “dump.” But the venue paid for it, so I can’t really complain. Instead, I recall a pearl of wisdom that was shared with me years earlier: “Keep your level of gratitude higher than your expectations.” God knows I’ve slept in worse. Besides, in a few hours we begin the pilgrimage to my own personal mythical motherland: Woodstock, N.Y., where my husband, Ray Wylie Hubbard, will play a show at Levon Helm’s Barn. I am beyond grateful …


The story really begins in 1964, when I was 7 years old and sitting two feet away from my family’s black-and-white television set. The Beatles were about to make history with their first live television performance in the U.S.A. on The Ed Sullivan Show. I needed to be close enough to kiss Ringo. He was my Beatle.

Music affects each of us in different ways. To some it is mere background noise; to others, a mood enhancer; many consider it the soundtrack to their lives. To me, it was a doorway to freedom, salvation — a respite from the chaos which was my life.

Here’s the Cliff’s Notes version: Dallas, Texas; five kids; Catholic schools; she hated me; he was never home; secrets; rage; and guns — lots of guns. In my childhood home there was a gun under every chair. My father wore a shoulder holster (and no, he wasn’t in law enforcement). Bless his heart, he is 84 and still packs a .38 every time he leaves the house. It wasn’t normal, but I didn’t know that at the time. Shit was going on that you didn’t talk about to anybody; the code was, “Keep your mouth shut.” So music became my escape. I could hide in my room, spin my records, put on headphones to tune out the noise, and dream of the day when I’d be old enough to leave my house of horrors.

The Beatles were my introduction. I was lucky, as the next 10 years brought me — and everybody else, whether they admit it or not — some of the greatest musical transformations in history. Rock, folk, country, blues, soul. The Band, the Byrds, Janis Joplin, Jimi Hendrix, Otis Redding, Donovan, Creedence Clearwater Revival, Bob Dylan, the Who, the Rolling Stones … they each had their own identity. I loved it all. By the end of the decade, songwriters were writing poetic tomes of social protest, giving the young generation a voice of its own. Folk and rock were crossing into each other’s territories. The musical education was plentiful, available, and all but unavoidable for anyone remotely interested. Me, I yearned for it.

It was 1969. I was 12. Plans were underway for a music festival to take place over three days on a farm in upstate New York. The festival was to be forever know as Woodstock. For me, records were no longer enough, I needed to experience the music live. I fought with my parents about it for weeks but there was no way they were going to let me go. As a parent I can look back and laugh at my unrealistic request (although I would have taken my son Lucas!) But at the time, I was devastated. So I found solace with my new friends — Marlboro Reds, Everclear and weed — and continued to dream of the great escape.

As it turns out, I didn’t have to go very far. By the early ’70s, the homegrown “Texas Music Scene” was already beginning to be recognized on a national level in magazines such as Rolling Stone and Billboard. Though “Texas” and “music” had long been synonymous, the sound coming out of the Lone Star State lacked a definitive description. Detroit was known for Motown, Memphis had Stax, New Orleans had funky R&B and Cajun, Nashville had country, but nowhere else but Texas could you find all of the above plus rock, Tex-Mex, folk and the blues all combined within the borders of one state (or in the case of Rolling Stone cover boy Doug Sahm, within a single artist.) At first, Texas country rebels like Willie Nelson and Waylon Jennings were kept at arms’ length by the music industry status quo, especially in Nashville; but once their freeform style of country music (alternately called “progressive,” “outlaw” and even “country rock”) took off back home, it was only a matter of time before Willie, Waylon and a host of others were making records on their own terms.

Judy holding court at Willie Nelson’s 4th of July Picnic in College Station, Texas, 1974. (Courtesy Judy Hubbard)

Judy holding court at Willie Nelson’s 4th of July Picnic in College Station, Texas, 1974. (Courtesy Judy Hubbard)

Early on in that cosmic cowboy boom period, Willie was throwing an outdoor music festival in his hometown of Abbott, Texas. This time I decided it would be better to ask forgiveness than permission, so a girlfriend and I ran away from home and headed to the big to-do. The repercussions I faced once I came back home the next day were worth it. Listening to songs over and over on a record player or on the radio was an important experience for me; but seeing the artist perform those songs live was not only more immediate, it was life-changing. The music went on all day, with artists frequently joining one another onstage. Willie called up a young songwriter to join him on a song and introduced him as Ray Wylie Hubbard. He was cute, outlaw, and oozed cool. Years later my girlfriend recounted to me that from that day on, every time we attended a show that Ray played, as soon as his set was over, I would turn to her and say, “One of these days, I’m gonna marry that Ray Wylie Hubbard.” One thing was certain: I had found my people. I was home. It was 1973. I was 16.

From that day forward anytime there was a music festival in Texas, I was there. In between festivals I would head to venues like the Armadillo in Austin or the Texas Tea House and Mother Blue’s in Dallas. Wherever Texas bands were playing, I went.

Returning home after one such event, my mother handed me an empty pillowcase with instructions to fill it with whatever belongings of mine would fit, and be out of her house for good in 20 minutes. It was non-negotiable. So with my new freedom, and the wisdom of a 16 year old, I left. To this day I’ve never spent a night in their house. I wasn’t quite prepared to be on my own, but I was ready. I had no idea how to go to a job interview, open a checking account or cook, but hey, I had skills: I could shoot a bird off a telephone wire from a moving car, run a casino out of a garage, and roll a joint with one hand.

A friend who was in his early 20s and had a house of his own took me in. In exchange for room and board, I was to feed the animals, keep the place tidy, the fridge full, and bullets stocked in the three re-loaders he had set up in the gun room. In exchange, I got my own room (complete with a waterbed which had a holster and small caliber gun attached to the back of the headboard), access to the drug box, and food. Other roommates would move into the house over the years. One played football for the Dallas Cowboys, while another was a world champion drag racer. It wasn’t a bad deal.

A 17-year-old, pre-Mother Hubbard Judy (center), during her stint as a door girl at Mother Blue's in Dallas in 1974. She doesn’t remember who the woman is, but the man is Don Sundeen, who was a promo rep for Capital Records. (Photo Credit: Ron McKeown)

A 17-year-old, pre-Mother Hubbard Judy during her stint as a door girl at Mother Blue’s in Dallas in 1974. The man is Don Sundeen, who was a promo rep for Capital Records. (Photo Credit: Ron McKeown)

I soon landed a job at Mother Blue’s as the door girl working until close. Then I’d hang after hours, when the staff and musicians would gather around drinking and telling road stories.  Occasionally I would work the after-hours poker games upstairs serving drinks. It wasn’t unusual for a game to include Freddie King, Bugs Henderson, Steve Fromolz and Eric Clapton. Some of the regulars who played the venue were King, Lightnin’ Hopkins, Willis Alan Ramsey, Rusty Wier, Howlin’ Wolf, Townes Van Zandt and B.W. Stevenson. Next door was a sister club, which brought in rock bands and stayed opened until 4 a.m. They became legendary due to the musicians who would drop by after playing arena shows in town: Alice Cooper, David Bowie, Robert Plant and Frank Zappa were just a few of the many artists who came in to relax, hang out, and listen to music.

One memorable night, a young songwriter playing the club asked me to go out after his show to see a band playing across town. We went to Fannie Ann’s and saw Ray Wylie Hubbard and the Cowboy Twinkies. My date joined them onstage for a song and we hung around after the show so the two could meet. It was the first time I actually met Ray. It was the first time Ray met Jimmy Buffet.

There was a price to pay for my youth, however. I had quit school, and my drinking and drug use continued to escalate. By  1975 it was out of control; I was drinking almost daily and was shooting heroin to feed my addiction. I eventually left the club in hopes that a regular day job would slow me down. It didn’t. I had averaged three trips a year to jail since I was 16 for drugs, fighting or driving crooked. Henry Wade, the District Attorney in Dallas, sat me in his office and told me it was over. None of my trading on family connections could get me out of the next scrape — he was revoking my get-out-of-jail card. It was my wakeup call. I felt like an old woman and I was tired. It was 1980. I was 22.

Living without drinking and getting high meant a total shift in my playmates and playgrounds. Although it doesn’t bother me at all to be around people drinking now, at first it was too difficult, so I stayed out of the bars and only went to an occasional concert. The movie Urban Cowboy had just come out, turning my two-stepping honky-tonks into country discos. John Lennon had been murdered, and hippies around the world were in mourning. I didn’t much feel like partying anyway. I had gotten a job in the car business and worked all the time. And twice a month, I would drive to the women’s prison in Gatesville, where I volunteered in a program for women in recovery. Trust me, that’ll keep you sober. It did me.


One night a friend asked me to go with a group to Poor David’s Pub in Dallas to see Ray Wylie. It was 1988, and I hadn’t seen or heard anything about him since the late-70s. He was funny, wore Cuban heels on his cowboy boots and looked even more like an outlaw than he did at that Willie festival back in ’73, but he was also sober — and his songs melted me. There was an eerie feeling that came over me, like I had been in love with him in another life. I couldn’t explain it but it was strong. After the show I hung out by the green room door waiting for him to come out. We chatted a bit and he asked me to come to his show the next night. Six months later, we were married. It was 1989. I was 31. We are still inseparable.

When Ray and I married, his music career wasn’t exactly on the front burner, and he wasn’t setting the world on fire. He simply played wherever and whenever he could. And while I had always been a music fan and had worked at a live music venue, that hardly qualified me to manage my husband’s career. That said, the simple fact was also that it wasn’t in my nature to not do anything about it, either.

By the time our wedding day rolled around I had helped out with a few contracts here and there, and began piecing together his history. I came to understand all too clearly that there were no plans for the future! So I came up with a plan: I had four days off from my job and intended to make good use of them, so I booked our honeymoon in Nashville. We would get married, fly to Nashville and stay at the Opryland Hotel, because one of my customers at the Lincoln Dealership was a VP and comped us the room as a wedding present. And while we were there, we’d hit Music Row and simply pick out our favorite record deal. I just knew that once these label execs heard Ray’s songs, they too would swoon and jump right on board, and then I could start looking for a sparkly red dress for all those award shows we would attend.

A story of such naiveté would be funny if it wasn’t dead on true! But this is how our Honeymoon really unfolded: While we were there, Nashville was hit by a rainstorm followed by a sleet storm followed by more rain. There were no doors open on Music Row, and the few phone calls we made to someone at a label — “a friend of a friend” who said they could get us in the door — all ended in the same polite “thank you; but no thank you.”

The best news of the whole trip was the giant food basket sent to our room as a wedding gift, because we were out of money by the third day and were hungry. But hey, I was in love, and Ray was grateful to have someone who believed in him — even if it was an uneducated used-car saleswoman with no music business experience.

He had no label, no manager, and no booking agent. He hadn’t released a new record in years. He was booking gigs at places where, before he’d gotten clean, he had previously been paid in booze and cocaine; places that hired bouncers with names like “Shit” and “Doodoo.”  I remember delivering a new Lincoln to a customer at his office one day. As he was congratulating me on my recent marriage to “that country star,” I glanced out the window in his office. The marquee across the street read: “Lingerie Show at 10:00, Ray Wylie Hubbard at 11:00!”

It was around this time I took over Ray’s booking. I made a list of all the clubs he had played the last couple of years and starting calling them. How different could this be than what I did at the car dealership all day? I worked in sales and leasing, but not walk-in customers; only referrals or customers I cold called. I was organized, knew how to follow up, and figured it would be a no brainer. On one of my first calls, a club owner told me the last time Ray played, he fell into the drums drunk, and would not be playing there again. Ray explained that it was not uncommon for them to confuse the “three- name guys,” and that must have been Jerry Jeff Walker, not him. “Well, that makes sense,” I thought, so I went back to smiling and dialing. The next one told me, “No way, he didn’t show up the last time we booked him.” I explained that it must have been one of those other three-name guys like David Allan Coe or Gary P. Nunn, as people often mix them up. “Well ask his band,” the club owner replied, “because they did show up!” Then he hung up.

There were no courses in what I was undertaking at the junior college, no books at the library, and certainly no one to show you the ropes. I had to make it up as I went along, as many in this position do. I went to every gig, as there were no roadies and Ray carried his own sound system. I would help with load in and out and collected the money at the end of the night. I still carried a gun, which was an asset at some of the honky-tonks he was playing at the time. One club owner in Dallas was notorious for shorting bands at the end of the night. He also had a reputation for being coked up, drunk, and a bully. The band waited in the parking lot (really!) while I went upstairs to settle up. He started in with the “you didn’t draw and I lost money” bit, setting me up to get stiffed. I wasn’t in the mood for him. I had just helped schlep the sound system down a flight of stairs in his shitty cowboy disco, sat through three one-hour sets telling one whiskey-breath dude after the next that I was not sitting alone because I was looking for love but rather because I was “with the band.” On top of all that I had to be at work at 8:30 in the morning and we needed the money! He pulled out a revolver and set it on the desk and continued to berate me. I pulled out my Walther PPK/S 9mm and set it on the desk and kept my mouth shut. Whatever my father’s parenting skills may have lacked, they made up for in dealing with situations like this. He taught me to never blink first and always use hollow point bullets. We got paid — which I’m sure had a lot to do with the guy thinking that the $500 he owed us was worth it just to make Ray’s heat-packing psycho wife with the bad bleach job go away.


Judy and Ray Wylie with their six-week-old son, Lucas, at his very first gig. Lucas now plays guitar in his dad's band. (Courtesy Judy Hubbard)

Judy and Ray Wylie with their six-week-old son, Lucas, at his very first gig. Lucas now plays guitar in his dad’s band. (Courtesy Judy Hubbard)

Little by little things moved forward. There were others out there who saw what I did in Ray and were willing to give him a chance. In 1992 we released his first CD, Lost Train of Thought, on our own. We had local distribution and sold it at gigs. A couple of years later he signed with a small independent label based in Austin and released Loco Gringo’s Lament. I was pregnant with Lucas at the time and still working at the car dealership while handling all the management and booking. When Lucas was born we hired a girl who was just starting a booking agency and was willing to take on Ray as a client. We moved to Poetry, Texas, which added an hour commute each way to my day job. It was incredibly hard doing everything ourselves, but we tried to remain grateful as we had our own little house on four acres in the country, our little hippie family and a belief that we were on the right path. Neither of us had family to babysit Lucas and it was still necessary for me to work the gigs so we took him with us. Recently, as I watched my now teenaged son playing lead guitar with his dad at a Gruene Hall show, I wondered if he remembered the many nights he slept in the T-shirt box next to me at the merch table at that same club.

In 1997, Auto Nation bought the Lincoln dealership I had worked at for the previous 17 years. I had a good deal going there; they were tolerant of me conducting music business out of my office and basically left me alone. But it was clear all that would change once the new corporation took over. I had never thought about what I would do if I didn’t work there. It had been my safety net when I got clean and sober. Our ultimate goal was for me to eventually be able to manage the business without having to work a day job, but we weren’t there yet. I didn’t exactly have a great resume, with no high school diploma, much less a college one. Hell, with my police record, I couldn’t get a job as a Wal-Mart greeter. I was terrified. Still, I called Ray and asked him what he would want to do if I quit my job.

“Move to Wimberley,” he said.


Lack of a formal education has been one of the few regrets I carry from my wasted youth. Could I have done a better job managing Ray if I had a college degree? Would I not live in such fear at the prospect of having to compete in the job market should I ever need to? I don’t know the answer to those questions. What I do know now is that an abundance of information is available on every aspect of the music business — if you really make an effort to find it. Once we were settled in Wimberley I began to study as if my livelihood depended on it. I joined industry organizations which offered networking and education. I scoured books and researched everything I could find on the Internet about publishing, management, recording contracts, publicity, social media, licensing for TV and film, and running an independent record label. I learned how to create a business plan, how to set realistic goals and work towards them. I subscribe to numerous music-industry dailies in order to stay current on trends, laws, and opportunities in the business. Each January, we review our progress and set new goals.

For many years I believed it was all about the record deal: If we could just get a record deal, success would follow. Or, if we could get with the right publisher, we would automatically start landing cuts on other artists’ records. Or, if we could get Ray on this festival, or an opportunity to open for that band on the road, then the rest of the world would see and love him, too. I have since learned it is not that black-and-white, that each artist follows a different path and finding your own is half the battle.

Over the years we have re-secured the rights to several of Ray’s old songs as well as three of his albums. We filed a lawsuit against a sleazy record label owner and won. We negotiated and sold rights to a screenplay Ray co-wrote which is now a feature film and includes four of his songs. Last year, we set up our own label, Bordello Records, and ran a successful release campaign, garnering a No. 1 spot on the Americana Chart as well as three nominations at the Americana Awards. And although he wasn’t happy with the final production of the aforementioned film and the nominations didn’t result in a win, I am reminded that getting to either one of those places without the help or backing of a major studio or record label is indeed quite an accomplishment.

Ray Wylie and Judy Hubbard backstage at Willie Nelson's Picnic in 2010. (Courtesy Judy Hubbard)

Ray Wylie and Judy Hubbard backstage at Willie Nelson’s Picnic in 2010. (Courtesy Judy Hubbard)

I continue to redefine my idea of what “success” is. It is certainly not what it was 23 years ago in a rainy Nashville hotel on my honeymoon. Do we have a fleet of tour busses, Grammys on the wall or sell out Billy Bob’s? Do I run with the hip crowd in the Texas music scene, vacation in Hawaii or have an entourage reminding me how great I am? Not even close. What I do have is 31 years without booze or drugs. I have a log home in the Hill Country where the sunset view on our front porch will take your breath away. I have a son starting college in the fall — a son who has never seen the inside of a jail cell and who has grown up loved and secure in the knowledge that no matter what he does, his parents will never throw him away. I have a husband who after 23 years still causes my heart to melt when he straps on his guitar, who continues to reinvent himself as an artist and who has added  “screenwriter” and “record producer” to his list of accomplishments. A husband who also now gets phone calls from people like Joe Walsh and Ringo Starr (who I still think of as my Beatle), inviting him to co-write, tour and just hang at their homes. And a husband who generously shares his knowledge with younger artists who look up to him.

Of course, there are days when one disappointment or another leaves me wondering if I’d be better of selling used cars again. But then, without fail, an email will come in. It will be from a bereaved father, recounting the first Ray Wylie Hubbard show he brought his son to 10 years ago and how they continued to attend concerts and share CDs until his son’s recent death — explaining that he just wanted to say thank you for the memories. Or it might be from a songwriter who has gone three days clean and sober and looks to Ray as an example of how to navigate this business without drinking. Or a young gal who loves “all things Red Dirt” and thinks “Ray Wylie is cool as shit!” Reading those emails, I am reminded of not only who brought us this far, but who continues to carry us when we want to give up.


We just finished playing the last song to a sold-out crowd at Levon Helm’s Barn in Woodstock. He invited Ray up to sing “The Weight” with him and his band, and asked our drummer, Rick Richards, to join him on drums. When the crowd cleared out and Helm’s band had all gone home, we joined him at his house to say our goodbyes. As we sat around his kitchen table laughing and telling road stories, I was once more acutely aware of how blessed my life has turned out to be. I really did end up marrying that Ray Wylie Hubbard guy. We have a son whose very existence makes my world a better place. And I finally made it to Woodstock. It was everything I had dreamed it would be.