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Steve Friess: There’s A Country-Western Song About Losing A Super Bowl Bet

Written By Steve Friess | Updated:
Steve Friess State Of Play: Sports Gambling Song

State of Play with Steve Friess

State of Play is a column that focuses on the trending stories in the casino and gambling space with sharp and clever insight from senior staff writer Steve Friess. Over his 25-year career, Friess has contributed to publications such as Newsweek, Time, New York Times and more.


The American songbook is replete with songs about gambling and, of course, music loaded with gambling lingo.

Kenny Rogers’ “The Gambler,” Elvis’ “Viva Las Vegas” and Lady Gaga’s “Poker Face” spring to mind but a poke around the Internet reveals there are tunes from everyone from Woody Guthrie (“Gamblin’ Man”) to The Clash (“The Card Cheat”) to AC/DC (“The Jack”).

The thing is, they are all about card and dice games, literally or metaphorically. Billy Joel perhaps strays the most into other forms — ponies, slots — in “Easy Money” when he sings, “Take me to the action/Take me to the track/Take me to a party if they’re bettin’ in the back.”

But songs that pivot on sports gambling?

Dale Hollow’s old-school country ditty “Fools Rush In” might be the only one. So far, anyway.

‘Dozens and dozens of dollars’

I admit, I don’t spend a ton of time with this genre these days, what with a devoted Swiftie of a 2-year-old daughter and a son who really rocks out to the Kiboomers and the Cedarmont Kids. (Look ‘em up.)

Fortunately, one of my editors came across Hollow’s song on one of the streaming services because he listens to “obscure Americana/southern rock music often.” The lyrics that caught his ear were:

That’s because I bet it all on black
Never thought that Tom Brady’d lead the Patriots ahead
And beat Jared Goff and the Rams behind
But now, I’m in this nice little predicament.

Hollow’s song is about a man struggling financially for many reasons but the big one is the bet he blew on the Super Bowl. He wrote it in 2019, but he updates the lyrics every year, subbing in the latest winning and losing QBs and their teams. The singer-songwriter tells me:

“If I need to pander to a local audience, say we’re playing in Kansas City, that’s one of those little moments built into the set where I could win over the audience. I can mention Patrick Mahomes and the Kansas City Chiefs, and they’ll cheer. And then, obviously in Philly, when we did Jalen Hurts line received a resounding response.”

Perhaps none of this would be remarkable if it weren’t for the fact that the song was also Hollow’s first minor hit. People like it. Spotify says it’s been streamed more than 500,000 times, which is not nothing and implies that it also has an audience on other platforms. That, he says, has netted him, “Dozens and dozens of dollars.”

A catalyst to get him to play

The obvious question about “Fools Rush In” is: Is it autobiographical? Did Hollow lose it all on a Super Bowl bet?

“No, no, no,” he laughs. “Despite the gist of the song, I’m much more cautious when it comes to my sports betting. I’m the type of person that will put maybe maximum $20 on a 10-to-15 leg parlay, go for those ridiculous odds and payouts. I haven’t had one hit yet, but I’ve had a couple that have come down to like the last two or three legs almost coming through. It keeps things interesting, but it’s not necessarily worrisome.”

He was inspired to give his “Fools Rush In” protagonist a sports gambling problem because he was writing the song in Nashville in 2019 around the time the Tennessee Legislature was legalizing sports betting.

“I had read something about the influx of sportsbooks that were going to descend upon Tennessee and Nashville, in order to try cash in on the gold rush that was bound to arise,” he says. “That got that thought in my head.”

Interestingly, he says, the song and that very onslaught of sportsbooks did have the effect of getting him to play a bit. “It really wasn’t until after the song that I started to get into gambling a little bit more, even though I’m not necessarily blowing every show’s paycheck on whether the Titans are going to cover the spread or anything like that.”

An honest, workaday quality

Hollow, born in Nashville and a recent transplant to New York City, spoke to me from a hotel in Salt Lake City where he had a gig Thursday night. He’s in his late 20s and is promoting his first full-fledged studio album, “Hack of the Year,” with a 15-city tour that began in Cleveland on Oct. 29 and culminates in Seattle on Nov. 19. After that, he says, he drives his van back to Nashville for Thanksgiving with family.

In other words, Hollow is what, if he were a professional gambler, we’d call a grinder. His lyrics are off-beat and, often, an attempt at self-effacing humor while the songs themselves have a traditional George Strait-style country sensibility. He’s nobody’s idea of a music sensation and it’s hard to imagine his path to becoming one, but there’s an honest, workaday quality to both his art and his nose-to-the-grindstone dedication that has yielded results.

Impressively, he actually supports himself as a musician. He says:

“It’s been a recent development, which I’m very grateful for. This career path in general is, I suppose pun-intended, is a gamble. I’ve gotten to the point where some people will ask me for advice on making a career as a performing artist, and I always say this: If there’s a million people that would love to be able to play guitar, 100,000 will go buy that guitar. Of that, there’s 10,000 that actually write a song. Of that, maybe 1,000 get to record that song. Of that,100 get to record a whole album, and of that, 10 get to go tour on it. And of that, one comes out making money. It is a gamble.”

New song sees some success

“Fools Rush In” was his most popular song until the new album hit. Now a single from the LP, “I’m a Lover But I Still Fight,” has had more than 1 million streams on Spotify. Like “Fools Rush In,” it’s got some pop-culture references mixed:

“And I’ve seen ‘Road House’ a hundred and twelve times
Instead of the dialoguе, I memorized the fights
So go ahеad, bust a glass
I’ll even give you one free swing, but then I’ll beat your ass
‘Cause it’s my way or the highway.”

That gives you a taste of his ouevre. It might not be your cup of tea. That’s fine.

But regardless of where he ends up in his career — whether he goes another 30 years performing at honky tonks and selling merch or quits to sell insurance — Hollow now has a distinction. He’s the author and performer of the one and only song I know of about sports gambling — so far.

Sounds like the stuff a Dale Hollow song might be made of.

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Steve Friess

Steve Friess writes the State of Play column for PlayUSA twice a week. He's a veteran gambling-industry reporter who began covering Las Vegas in 1996 and covered the openings of resorts in Asia, Europe, and across the U.S. His bylines have appeared in The New York Times, Playboy, New Republic, Time, BusinessWeek, Newsweek, New York magazine, and many others. He, his husband, their children and three Poms live in Ann Arbor.

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