This is the first potentially "embarassing" song to come up for SOTD, and well, its not even that bad. This song has been a favorite of mine for a long time, sadly, ever since I got a hold of a dirty, scuffed 45 RPM copy of "The Gambler" at a flea market for 10 cents when I was a kid. Most of my early memories of the song revolve around an odd Muppet Show skit centered around the song. Odd when you consider muppets (a) gambling, (b) drinking whiskey and (c) hanging out with Kenny Rogers. The images of the old muppet on the train telling Kenny about the secret to surviving stuck with me and when I could sit back and listen to the crackling and popping of the old 7", it was like comfort food in audio form. Even today when my copy of "The Gambler" comes in perfect digital version (althought sometimes I wish I could listen to a digital version of the 45). Kenny himself is a bit of a icon of a bygone era. His bread, his flowing pile of greying hair. He'd never be a star today. He's sort of the lighter, safer, softer version of Willie Nelson, especially when you start considering his even-more-embarassing hits like "Lady". "The Gambler," however, has the same charm as something like "Wreck of the Edmund Fitzgerald" and more charm than dreck like "American Pie". It's cheesy, Disney-style Americana.
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