They don’t call it “outlaw country” for nothing, and Willie Nelson has never been one to follow the rules. Nicknamed the Red-Headed Stranger, he built his career on doing things his own way—even when the industry pushed back. One of the best examples of that spirit came on this day in 1976, when Nelson’s 20th studio album, The Troublemaker, reached No. 1 on Billboard’s Top Country Albums chart.
A Gospel Album That Almost Never Came Out
What many fans don’t realize is that The Troublemaker was actually recorded years earlier.
In April 1972, Nelson recorded “Mountain Dew,” his final single with RCA Records. The label tried to lock him into an early contract renewal, hinting they might not release more of his music if he refused. He walked away anyway.
Not long after, while visiting Nashville, Nelson met Atlantic Records executive Jerry Wexler at a party hosted by songwriter Harlan Howard. Wexler was impressed by Nelson’s songs, especially after hearing material that would later shape Phases and Stages. When Atlantic launched a country division, Nelson became its first signing.
Wexler gave him studio time in New York City, where Nelson recorded a collection of gospel songs performed in a raw, honky-tonk style. Those sessions would become The Troublemaker.
Shelved, Then Resurrected
Unfortunately, weak sales from Nelson’s earlier Atlantic albums convinced the label the gospel project wouldn’t sell. The album was shelved, and when Atlantic eventually shut down its country division, Nelson moved on—this time signing with Columbia Records, where he finally gained full creative control.
By the time The Troublemaker was finally released in September 1976, Nelson was coming off the massive success of Red Headed Stranger. As Rolling Stone famously joked in early 1977, he could have recorded Hamlet and still sold records.
Once released, The Troublemaker proved the doubters wrong. It hit No. 1 on Billboard’s Hot Country Albums chart, and the single “Uncloudy Day” climbed to No. 4 on the Hot Country Singles chart.
The Album That Reunited a Family Duo
The Troublemaker also marked the beginning of a legendary musical partnership—with Nelson’s older sister, Bobbie Nelson.
Living in Austin at the time, she received a call from Willie asking her to join him in New York.
“I had never been on an airplane or gone farther than Nashville,” Bobbie later recalled. “But I went to New York, and we recorded The Troublemaker—the first time I ever recorded with him. Then we did Shotgun Willie, and it all felt so natural. Willie told me, ‘I’ve missed playing with you. Let’s not stop.’”
They didn’t. Bobbie became a permanent member of the Family band and toured alongside her younger brother for decades, remaining by his side until her death in 2022 at the age of 91.