Kenny Rogers' Gambler Gives The Worst Advice Ever: Existentialism On The Rails
Kenny Rogers’ “The Gambler”—it’s not just a song, it’s a life lesson. It is that song that your dad plays every time you’re stuck in traffic, and he’s reminiscing about his misspent youth or, worse, his theoretical misspent youth because he never gambled but thought he could’ve.
And the lyrics. They sound like your grandpa trying to impart wisdom after drinking a few beers, and you think, “Oh God, Grandpa’s doing the thing again.” The story starts with this guy on a train—which, are we still doing that? Is this 1870? Who’s just hopping on a train and having a philosophical conversation? I digress.
Our random guy sits down with The Gambler—and you know right away he’s The Gambler because he’s described with that capital 'G' energy. This man is not just dabbling in blackjack at a basement game on Friday night. No. This man lives for the cards. And this Gambler, who is very approachable, says, “Hey, kid, let me drop some wisdom on you (after asking for liquor).” Sure, that’s a way to ease the tension in a cramped train compartment; a stranger wants to tell you his life lessons for free whiskey. There’s no way this could go wrong. Is this a Kenny Rogers song or a Lifetime movie? Again, I digress.
Here’s the best part. The Gambler’s wisdom—get ready for this—is: “You gotta know when to hold ‘em, know when to fold ‘em, know when to walk away, know when to run.” This is excellent advice if your primary concern is winning at poker or evading the police after a heist. Other than that, it stinks.
And now the crazy part: people take this as serious life advice. Okay, but how often are you just sitting around, holding cards, wondering if you should fold or sprint out of the casino? Not often! If it’s often, we have another conversation to have.
Yes, people love this advice. I’ve encountered individuals all over the world who believe, “This applies to everything.” And I think, “Really? To everything?” If you’re at a job interview and they ask about your greatest strength, are you supposed to say, “Well, I always know when to hold ‘em… and when to fold ‘em.” That’s how you end up running from that job interview. You are not going to be hired.
The line that kills me is, “The secret to survivin’ is knowin’ what to throw away and knowin’ what to keep.” Oh, wow, thank you, Kenny Rogers! That advice would’ve saved me when I bought a Pelaton that turned into a glorified laundry rack within two weeks. “Know what to throw away.” Yeah, I wish I had known that then. You think The Gambler would’ve been at my door telling me, “Richard, toss the Pelaton. You’re not that kind of person.”
Then, of course, The Gambler dies at the end of the song. Did you see that coming? I ask, “Whoa, whoa, we were just talking about cards here! Why’d you have to make it dark?” But that’s what happens—he kicks the bucket when you’re starting to lean in. It’s as if he delivered a TED Talk on poker and existentialism and then vanished like Yoda in Return of the Jedi. The guy’s out, mic drop. He’s done.
I guess that’s the point. Kenny Rogers and his Gambler want us to think deeply about life. And now we’ve got to figure out if we’re holding, folding, or running from ‘em. I hope I don’t gamble all my chips away thinking I’m being profound. Have a drink of my whiskey, and we’ll see.