"Kentucky Gambler" is a 1974 song written and performed by Dolly Parton. "Kentucky Gambler" was issued as a track from Dolly Parton's, The Bargain Store album from 1975. That same year, Merle Haggard, covered "Kentucky Gambler" where it was his nineteenth number one song on the country chart. (Coincidentally, Parton's The Bargain Store album featured a cover of a Haggard composition, "You'll Always Be Special to Me".) The Merle Haggard version stayed at number one for a single week and spent a total of eleven weeks on the chart. (The following year, Haggard would cover another Dolly Parton song, "The Seeker".)

A classic Dolly Parton story song, "Kentucky Gambler" tells the story of a miner from Kentucky who abandons his wife and children for the bright lights of Reno, where he initially does very well at gambling, "winning at everything he played". Eventually, however, his winning streak comes to a halt, as he loses all of his winnings. Broke, he returns home, only to find that his wife has found someone else and has moved on without him. He concludes that "a gambler loses much more than he wins".

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