“The Gambler” was written by the Nashville songwriter Don Schlitz. With the classic chorus lines, “You’ve got to know when to hold ’em, know when to fold ’em,” the song is told from the first-person perspective about a conversation with an old poker player on a train. The card shark gives life advice to the narrator in the form of poker metaphors, before presumably dying in his sleep. According to the Reader’s Digest Country and Western Songbook, Schlitz wrote the tune in honor of his late father, “the best man I ever knew.” “He wasn’t a gambler,” he explained. “But the song was my way of dealing with the relationship that I had with him.”

Don Schlitz wrote this song in August 1976 when he was 23 years old. It took two years of shopping the song around Nashville before Bobby Bare recorded it on his album Bare at the urging of Shel Silverstein. Bare’s version didn’t catch on and was never released as a single, but other musicians took notice and recorded the song in 1978, including Johnny Cash, who put it on his album Gone Girl.
It was Kenny Rogers who finally broke the song loose, in a version produced by Larry Butler. His rendition was a #1 Country hit and even made its way to the Hot 100 at a time when country songs rarely crossed over.

This song had a huge impact on both Kenny Rogers and its writer Don Schlitz. Rogers had three #1 Country hits under his belt, but “The Gambler” gave him the title track to his biggest-selling album. Schlitz was able to quit his day job (actually a night job – he worked the graveyard shift) and become a full-time songwriter. Some of his other songs include “He Thinks He’ll Keep Her” by Mary Chapin Carpenter and “On the Other Hand” by Randy Travis.

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