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, so Schlitz recorded it himself, but this version failed to chart higher than #65. However, other musicians took notice and recorded the song in 1978, including Johnny Cash, who put it on his album Gone Girl. However, it was Kenny Rogers who finally broke the song loose, in a version produced by Larry Butler. His version was a #1 Country hit and even made its way to the Pop charts at a time when Country songs rarely crossed over. It was released in November 1978 as the title track from his album The Gambler which won him the Grammy award for best male country vocal performance in 1980. In 2006 Don Schlitz appeared in the Kenny Rogers career retrospective documentary "The Journey", where he praised both Rogers' and Butler's contributions to the song stating "they added several ideas that were not mine, including the new guitar intro".

It was one of five consecutive songs by Rogers to hit #1 on the Billboard country music charts. On the pop chart, the song made it #16 and #3 on the Easy Listening chart. It's become one of Rogers's most enduring hits and a signature song. As of November 13, 2013, the digital sales of the single stood at 798,000 copies.

The song itself tells the story of a late-night meeting on a train "bound for nowhere" between the narrator and a man known only as the gambler. The gambler tells the narrator that he can tell he is down on his luck ("out of aces") by the look in his eyes and offers him advice in exchange for his last swallow of whisky. After the gambler takes the drink (and a cigarette), he gives the following advice:

Know when to walk away, know when to run.
You never count your money when you're sittin' at the table,
There'll be time enough for countin' when the dealin's done.

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