On February 9, 1969, Waylon Jennings‘ band member Walter “Chuck” Conway was killed, and another Rags Allen was badly injured when their camper crashed en route to a show in Illinois. At the time, Jennings was shaken up by the tragedy, which happened nearly a decade to the day his former friend, mentor, and bandmate Buddy Holly lost his life in a plane crash. To make matters worse, Jennings was also in the throes of his drug addiction by the late ’60s.
Not long after the accident, Jennings was in a dark place and sat down for a poker game one night with Merle Haggard and his manager, Fuzzy Owens. By the end of the evening, Haggard and Owens had wiped Jennings clean.
“Merle Haggard and his manager, Fuzzy Owens, got me in a poker game and cleaned me out,” recalled Jennings in his 1996 book Waylon: An Autobiography.”I had four or five thousand dollars on me, and they won everything.”
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Jennings was under the impression that there was something malicious about Haggard and Owens’ intent that night. “They were there to get my money,” said Jennings. “That was it. I think Merle is a great singer and songwriter, and he was probably in as bad a shape as I was, but we’ve never been close since that night. I can still remember their faces.”
He continued, “When I was broke, they said their goodbyes and left. I never forgot that.”
Regardless of the ill-fated poker game, the two still held a mutual respect for one another as artists but kept their relationship at a distance, never becoming close friends. Jennings also took on four of Haggard’s songs, which he recorded on three of his albums. Here’s a look behind his Haggard covers.
[RELATED: The Love Song Merle Haggard Wrote for His Crush Dolly Parton]
“Today I Started Loving You Again” (1968)
Written by Merle Haggard and Bonnie Owens
In 1968, Merle Haggard released “Today I Started Loving You Again” as a B-side to his No. 1 hit, “The Legend of Bonnie and Clyde.” Unfortunately, the single, which was co-written and featured his then-wife Bonnie Owens, didn’t chart, but it ended up getting a second life on Jennings’ 1968 album Jewels.
Following Jennings’ lead, Conway Twitty and Jerry Lee Lewis also released versions of the song in 1968, along with later covers by Kenny Rogers and the First Edition, Emmylou Harris, Skeeter Davis, Dolly Parton, and many others. In 1997, Haggard rerecorded “Today I Started Loving You Again” with Jeff Carson for Carson’s album Butterfly Kisses.
“My Ramona” (1968)
Written by Merle Haggard
On Jewels, Jennings also took on a cover of his future Highwaymen bandmate Johnny Cash‘s “Folsom Prison Blues,” along with songs by his mentor Harlan Howard. Closing the album was a second song written by Haggard, “My Ramona.” The lyrics follow a young love who was left behind—They’re just going by the way she’s acting now / I just can’t believe the things they say about her / ‘Cause Ramona knows the things I won’t allow.
“All of Me Belongs to You,” featuring Anita Carter (1970)
Written by Merle Haggard
Haggard first released “All of Me Belongs to You” on his 1967 album with the Strangers, I’m a Lonesome Fugitive. Just three years later, Waylon kicked off the 1970s for Jennings with his cover of Chuck Berry’s”Brown Eyed Handsome Man,” which went to No. 3 on the Country chart. The album also features his rendition of Haggard’s song from ’67.
“Tonight the Bottle Let Me Down” (1978)
Written by Merle Haggard
The final song Jennings recorded by Haggard was “The Bottle Let Me Down” on his 1978 album I’ve Always Been Crazy, which went to No. 1 on the Country chart. Jennings’ version was retitled “Tonight the Bottle Let Me Down.” Haggard originally released the song, about a man who can no longer find comfort in the bottle after losing his love, on his 1966 album Swinging Doors and the Bottle Let Me Down, which peaked at No. 3.
Photo: Waylon Jennings, 1970 (Frank Edwards/Fotos International/Getty Images)
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