By the time Waylon Jennings walked into a Phoenix church to marry Jessi Colter in October 1969, he already had three divorces behind him.

When Waylon Jennings walked into Glencroft Studios in Nashville in January 1974 to record a song he had written for his fourth wife, Jessi Colter, the 36-year-old singer had been recording country music for nearly a decade without a single No. 1 hit to his name.

Five years earlier, before marrying Colter in Phoenix on October 26, 1969, Jennings had convinced himself that he was simply not cut out for domestic life. Between 1956 and 1968, his three marriages to Maxine Lawrence, Lynne Jones, and Barbara Rood had all ended in divorce, strained by 300-day road schedules, tight finances, and the unresolved survivor’s guilt he carried after giving up his seat on the February 1959 flight that killed Buddy Holly.

While sharing a bachelor apartment in Nashville with Johnny Cash after his third marriage collapsed, Jennings leaned into the restless drifter persona that defined his early RCA Victor recordings. That outlook shifted in 1968 when he returned to Phoenix, Arizona, where he had once fronted his band The Waylors at a club called JD’s, and stepped into Audio Recorders studio to help produce a session for Mirriam Johnson.

Performing under the stage name Jessi Colter—an alias borrowed from her great-granduncle, a member of Jesse James’s outlaw gang—she had recently ended her marriage to rock-and-roll guitarist Duane Eddy and was raising their young daughter, Jennifer, on her own. Jennings signed a production contract with Colter and helped land her a recording deal with RCA, and by the time they exchanged vows at a church in Phoenix in the fall of 1969, he had adopted Jennifer and moved Colter into his life in Tennessee.

Determined not to let the road ruin a fourth home, Jennings sat down and wrote “This Time,” a straightforward country shuffle that owned up to his reputation as a rambling man while promising his wife that he intended to make their marriage stick.

After negotiating a landmark contract with RCA in 1972 that gave him the right to produce his own sessions with his touring band, The Waylors, rather than relying on label-assigned studio crews, Jennings brought “This Time” into Glencroft Studios—a former church in Nashville owned by gospel singer Roy Wiggins. Co-producing the track alongside Willie Nelson, Jennings cut the song with his regular road lineup, including drummer Richie Albright, steel guitarist Ralph Mooney, and bassist Duke Goff.

Released in the spring of 1974 as the title track of his twentieth studio album, “This Time” climbed to the top of the Billboard Hot Country Singles chart in June 1974, giving Jennings the first solo No. 1 record of his career.

Within months, Colter became a star in her own right when her self-penned ballad “I’m Not Lisa” crossed over from country radio into the pop Top 5 in 1975. The following year, the couple stood at the center of the outlaw country movement on the compilation Wanted! The Outlaws, singing duets on “Suspicious Minds” and “Good Hearted Woman” as the record became the first album in country music history to be certified platinum.

Success on the charts did not spare their home from the habits Jennings had built during his decades on the highway. After welcoming their son, Waylon Albright “Shooter” Jennings, in May 1979, the marriage nearly broke in the early 1980s under the strain of Jennings’s $1,500-a-day cocaine addiction and the financial trouble that followed.

In 1982, Colter separated from him and took three-year-old Shooter back to Arizona, telling her husband that she loved him too much to sit by and watch him destroy himself. Rather than letting the marriage end like the three before it, Jennings worked to repair their trust, and in 1984—after seeing five-year-old Shooter imitate his habits with a canister of white powdered foot medicine—he rented a house in the Phoenix area for a month and quit cold turkey with Colter and their son beside him.

Four years later, in December 1988, Colter helped see him through emergency triple-bypass heart surgery, after which he also gave up his six-pack-a-day cigarette habit.

In their later years, as Jennings battled severe diabetes and circulation problems that forced the amputation of his left foot in late 2001, the couple returned permanently to Arizona, settling in Chandler. He died there in his sleep on February 13, 2002, at age 64, with Colter still beside him thirty-three years after they stood in a Phoenix church and twenty-eight years after he put a promise to her onto the country charts.