18. “The Gambler,” Kenny Rogers, 1978

Kenny Rogers’ humble little storytelling ditty was huge. It was a massive crossover hit, and it spawned a series of TV movies that Rogers even starred in during the height of his popularity. I can’t even count the number of times I listened to this song in my youth. The great thing about this song is that literally anybody can sing along with it, since Kenny is only half-singing.

This is a great song, by anybody’s metric. It’s also a sneakily dark one, as the lyrics suggest that the gambler actually dies at the end of the song. Rogers performed this song on about a million shows, including The Muppet Show, and the track is so closely associated with him that one of his nicknames is, in fact, “The Gambler”.

I don’t care who you are or when you were born, or how ridiculous you think Rogers is with his facelift and his chicken restaurants, this is among the best songs ever written (by some fellow named Don Schlitz, according to Wikipedia).

Favorite Lyric: “The best that you can hope for is to die in your sleep.”

Favorite Musical Moment: It is a very simple song, musically, but I love that little water-drip percussion effect, mainly because it totally doesn’t need to be there, but it is, and it’s awesome.

Would It Make Good Karaoke? Yes, but be aware that there’s probably some 50-year old dude who sings this every night, so make sure you don’t step on anybody’s toes.