Merle Haggard was a late starter in the country charts, but some of the reasons are well known. Between 1957 and 1960, he served nearly three years for burglary in San Quentin, that facility later to be made famous by another country icon, Johnny Cash. But on December 28, 1963, signed to the small Tally label, he entered the country countdown for the first time with “Sing A Sad Song.”

The song was written by Wynn Stewart, one of the originators of the Bakersfield sound that grew up as an alternative to the increasingly smooth Nashville production template. Stewart was a familiar figure on the country scene from the mid-1950s, charting regularly until the end of the 1970s.

As Haggard attempted to build up his career and reputation upon release from jail, he sat in with Stewart’s band on bass while the frontman was out of town. Wynn was sufficiently impressed to hire him, and Merle played on Stewart’s version of “Sing A Sad Song.”

Starting his solo Tally

When Haggard landed a deal of his own on Tally, run by cousins Lewis Tally and Fuzzy Owen, the track was chosen as his first single. Distribution was by Fabor Records, and the single carried a credit for accompaniment by the Wynn Stewart Orchestra, returning the favor to Haggard.

The track debuted on Billboard’s 30-position Hot Country Singles chart for that last week of 1963 at No.29, shortly before the survey expanded to 50 titles. Buck Owens was in the middle of an epic 16-week run at No.1 with his Capitol single “Love’s Gonna Live Here.” Haggard’s 45 went on to reach No.19, before he placed three more Tally singles on the chart. He cracked the Top 10 for the first time with his early signature “(My Friends Are Gonna Be) Strangers.”

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By now, Merle’s progress had been noticed by Capitol, who persuaded him (after some initial reluctance and loyalty to Tally) to sign with the major. They acquired his early sides including “Sing A Sad Song” and “(My Friends Are Gonna Be) Strangers,” both of which appeared on his debut album Strangers, released by Capitol in 1965 alongside a selection of new recordings. The Hag was well and truly and up and running.

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