The year was 1989.
Despite the demise of the Dillo a decade earlier, the Austin music scene was thriving. Touring acts from rock to reggae to punk to world beat played Liberty Lunch. Antone’s hosted blues masters for fans every night of the week. Honky-tonk heroes played the Broken Spoke and clubs featuring live music lined 6th Street. The third year of the new South by Southwest music festival featured over 300 bands and 3,000 attendees. Joe Ely won Musician of the Year in the Austin Music Awards and Poi Dog Pondering was recognized as the Best New Band.
And my young cousin, Will T. Massey released “Slow Study,” his third independent release.
Will blew into Austin from his west Texas hometown of San Angelo to go to college. But Will, who started writing original songs in high school, quickly discovered the various open mic nights for musicians around Austin. His family’s college plans for him quickly faded into his own dreams of making it big in music. He found a home away from home at the Chicago House coffeehouse, run by Peg Miller & Glynda Cox, who hosted theatrical productions, music, and the hottest open mic in town. Will quickly became a regular. Eventually, they put him to work sweeping floors since he was always hanging around, and let him move into an old stone sheep-herder’s shelter on their land since he had no money.
Will had already released two cassettes, “Pickin’, Poker, and Pick-up Trucks” and “Kickin’ Up Dust.” For his third record, legendary West Texas musician/producer, Lloyd Maines, pulled in a panoply of great Austin musicians to back Will on a new set of songs.
On a Saturday night in September 1989, Will welcomed a crowd of friends and fans to “my living room” as he jokingly called Chicago House that night. I managed to record the evening on a little stereo Sony Walkman. I recently recovered those tapes and digitized them, posting some of those songs on my YouTube channel.
Rough as the tapes are, they display a young singer-songwriter totally in his element, enjoying his audience and welcoming musical cohorts to share the stage and evening with him. Will told stories and jokes, played some of his old favorites, but mostly focused on playing the new tunes from the cassette, of course. Through the evening, he welcomed other musicians to take a turn on the stage, including Butch Hancock and Jimmy LaFave. Jesse “Guitar” Taylor accompanied Will on a number of his rocking tunes, and rockabilly sweetheart, Rosie Flores, joined them for a couple of songs, including this hidden gem: a tune co-written with Rosie Flores. To my knowledge, this tune has never appeared anywhere else and I doubt either one of them performed it often, so I’m delighted to share it with you here.
Drive down the road, hon —
Come back to me,
Take a left at Lonesome,
Hang a right on Memory,
Take the Trail of Tears
To the Home of the Blues —
I’ll always be here,
Waiting on you.
“Slow Study” would be Will’s last independent release before his MCA record. The following spring, he packed Chicago House to the rafters during SXSW and signed the record deal shortly thereafter. His eponymous release in 1991, produced by Roy Bittan of Bruce Springsteen’s E-Street Band and featuring a host of heavy hitters backing him, garnered Will rave reviews in Rolling Stone and Time magazine.
By the time he played SXSW in 1991, Chicago House was so packed, I could not get in for his performance. I waited outside for a chance to talk with him. He had a distant look about him as he stood on the sidewalk in the Austin evening, sporting a beret rather than his old cowboy hat. He was already flying skyward on his rocket ride to widespread fame and international touring.