Let’s just get this one out of the way, straightaway: “The Gambler” by Kenny Rogers is, objectively, the greatest song about gambling that’s ever been written and recorded. It might strike some as (way) overplayed, too cliche, et cetera, but no tune — entertainment franchise, really — has done more to make gambling seem super dang cool than Mr. Rogers’ barroom singalong.
As for the rest? Well, the Grateful Dead sang about gambling so frequently that they’ve already earned their own entire listicle on this website. When you’re grateful to merely be dead, what have you got to lose? From there, it’s subjectivity city, and the following list is unranked. So feel free to debate this music of chance on social media ad nauseam as you listen to it in the background all day — or, if you’re as lucky as Kenny, deep into the night.
“Heads Carolina, Tails California,” Jo Dee Messina. As a child, your first wager likely involved a coin — first flipped, then won or lost. The stakes were, clearly, extremely low. Now imagine you’re a young adult in love, looking to put down roots with someone you think you’re in love with, someone who could be forever. When determining where to live, the prudent course of action would be to look at jobs, schools, cost of living, and the like. But Jo Dee Messina? She picks two potential destinations that couldn’t be more different and just flips a damn coin. That’s true risk.
“Atlantic City” and “Roll of the Dice,” Bruce Springsteen. The first of this couplet is one of the Boss’ best-known tunes, all darkness and desperation and a Boardwalk’s slip away from falling into the ocean and drowning, either literally or in one’s sorrows. The second, off the relatively obscure Human Touch, is peppy and full of hope. “All my elevens and sevens/Been coming up sixes and nines/But since I fell for you, baby/Been coming on changin’ times.” If only it were that easy.
“Train of Consequences,” Megadeth. The bad acid trip version of “The Gambler,” this song sounds like how it feels to chase bad bets until you pass out in a puddle of rainwater near a Dumpster and then wake up in the morning feeling like you’ve been kicked in the head repeatedly. In other words, a very realistic approximation of a rough night at the tables.
“Blackjack,” Ray Charles. At first listen, this song makes “Train of Consequences” sound like “Puff the Magic Dragon.” Unlike a lot of gamblers, however, Mr. Charles’ narrator owns the fact that it’s his fault and his fault alone that every quarter he gets, blackjack takes it away. With rock bottom plainly acknowledged, recovery might be right around the corner.
“Ooh Las Vegas,” Gram Parsons. A buffet of great gambling lyrics that takes on an air of added poignancy if you’re aware of the behavior that led to Parsons’ premature demise. “I spend all night with the dealer/Tryin’ to get ahead/Spend all day at the Holiday Inn/Trying to get out of bed.” Heavier than heavy, man.
“Leaving Las Vegas,” Sheryl Crow. A perfect palate cleanser after Parsons’ tune, Crow’s down-on-(and dancing in)-her-heels narrator decides to cut her losses in the desert, leaving us with this fabulous rumination on vocational navigation: “Such a muddy line between the things you want and the things you have to do.” Indeed.
“The Race Is On,” George Jones. The ultimate gambling band, the Grateful Dead, covered this country classic, in which one of the genre’s foremost standardbearers uses horse racing to frame a soul-crushing breakup. “Somebody new came up to win her/And I came out in second place.” That’s almost as bad as watching your last dollar go into a teller’s palm. Almost.
“There’s a Place in the World for a Gambler” and “Run for the Roses,” Dan Fogelberg. Who knew such a soft rocker could be such a diehard gambler? Honestly, though, the first of these tunes, in spite of its on-the-nose title, is more of an excuse for Fogelberg to let his gorgeous voice drip all over a piano-backed track than a song about … something. The lyrics are extremely opaque; interpret them as you will, and then have a good cry. The second ballad is very specifically about a young horse being reared up to run on that first Saturday in May at Churchill Downs, and is touching enough to get PETA protestors to put their signs down and clap.
“Lawyers, Guns & Money,” Warren Zevon. There’s problem gambling, and then there’s gambling to the point where your life is literally in danger. And what’s truly scary about this song is not that Zevon — having “taken a little risk” in Havana, where “the Russians” hold sway — is attempting to marshal the unholy trifecta of lawyers, guns, and money, but that he has to ask his dad for help. That’s when you know you’re really in deep.
“Mississippi Flush,” Ray Wylie Hubbard. At least Warren had his father to get him out of this. Ray Wylie Hubbard has no such luck, nor does he seem to want it. The game he’s involved in, five-card draw, appears to have mortal stakes. But you quickly get to wondering, what with Mr. Ledbetter and Saint John showing up, whether we’re not in the realm of something far more terrifying and consequential than a deck of cards.
“Roll the Bones,” Rush. Rush sucks and so does this song. But it incorporates a heaping helping of gambling imagery, and enough people love Rush that we’re including it anyway. Enjoy — or, likelier, don’t.
“When You’re Hot, You’re Hot,” Jerry Reed. In this rollicking tune, far as we can tell, some hillbilly gets arrested for catching a heater during an illegal game of back-alley craps. He gets 90 days and then threatens to take the judge out in that same alley and beat the snot out of him. We assume that led to him having to serve additional jail time, but the song ends before the sentence is handed down.
“Still the Same,” Bob Seger. It all works out for some people, y’know? The highs aren’t too high and the lows aren’t too low. Game to game, you’re still the same. And that’s great. Just don’t get lulled into thinking it applies to you or anyone outside of Bob Seger’s immediate circle of friends.
“Every Breaking Wave,” U2. This might seem like a reach until you consider that the federal judge in the Ivey v. Borgata edge-sorting case opened her 2016 opinion by quoting the following lyrics from this song: “Every breaking wave on the shore/Tells the next one ‘there’ll be one more’/Every gambler knows that to lose/Is what you’re really there for.”
