And Now, The Definitive EV Ranking Of Gambling Songs By The Grateful Dead

The band wasn't all sunshine and roses, as the Dead's lyrics sometimes turned toward cards and dice
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The songbook of the Grateful Dead covers a lot of ground. From psychedelic rock to jazz, country to bluegrass, you name it, the Dead did it.

And their lyrics were as eclectic as their musicianship, covering anything and everything you could think of — including gambling.

Actually, a lot of gambling. In fact, no less than 15 times did the Dead do a ditty about dice, doubling down, or other, non-alliterative gambling terms and stories.

“This is amazing,” said fan of the band Adam Levitan, co-founder of the sports gambling site EstablishTheRun.com, when informed about the sheer volume of gambling references. “I never really noticed so much gambling in these songs. I always loved ‘Dire Wolf,’ mostly because I’m always afraid a stranger is going to murder me.”

Well hang on there Adam, as there will be no murder in the following — just a long, strange trip through the Grateful Dead’s catalog of gambling-related songs and lyrics.

Please note they are ranked in order of expected value (EV) of the gambling reference, from most +EV to least, because of course they are.

Ramble On Rose

While the lyric “the grass ain’t greener, the wine ain’t sweeter” may be the song’s high point, “sittin’ plush with a royal flush, aces back to back” is certainly a poker player’s dream. A pair of aces in the hole, with one of them suited to the ten, jack, queen, and king up top. Hopefully you bet heavy and a lot of the table kept up. At any rate, you can’t get much more +EV than this, with the odds shorter than Bobby Weir’s late-1980s clothing choices.

Scarlet Begonias  

One of the Grateful Dead’s most upbeat and popular tunes, it features the following lyric, which begs for some analysis: “In the thick of the evening, when the dealing got rough, she was too pat to open and too cool to bluff.” Let’s break this down, shall we? If you’re “pat” in any type of draw poker, it means you’re not taking any cards. Maybe you have a great hand, maybe you’re bluffing, but either way, you’re not drawing. So she’s pat. Now take in the fact she’s not going to bluff, and all indications now point to her holding the goods. Add it up, and even though she’s got rings in her fingers and bells on her shoes, she’s looking like someone who’s taking the pot.

Here Comes Sunshine

Certainly a lesser Dead tune — they didn’t play it once in concert from 1974 to 1992 — but it ranks high on the gambling list with the key lyric being “line up a long shot maybe try it two times, maybe more.” Way I see it, you catch a break, that long shot comes in early, you’re golden. And even if it doesn’t, you’ll have multiple chances to hit that score. This is like the theme song for playing low-stakes GPPs. Like the DraftKings Millionaire Maker. Just one time, baby … 

Deal

This is a straight shooter of a song, from the title right on down. The song is basically about a gambler who doles out advice from both sides of his mouth. To wit: “Wait until that deal come round, don’t you let that deal go down, no, no” demonstrates the yin and yang of the gambler’s life. The key lyric for my money, however, and the reason “Deal” scores high on the EV ranking is this: “I been gambling here abouts, for ten good solid years. If I told you all that went down it would burn off both your ears.” Way I see it, if anyone has been gambling “here abouts” for a full decade, you’d have to assume they’re profitable. Plus, there’s the rock-solid advice later in the song: “Watch each card you play, and play it slow.” All in all, we have ourselves a gambling winner here.

Stella Blue

A bittersweet Dead tune, not only because of the lyrics (such as, “There’s nothing you can hold for very long”) but also due to the fact they debuted the song on what ended up being Pigpen’s last show with the band. [Editor’s note: what the heck is a “Pigpen”?] The song does contain the following nugget: “When all the cards are down and there’s nothing left to see,” which indicates to me the river card (or seventh street if we’re playing a stud variant) has been dealt, and we have a good sense of where we stand in the hand. We’ll call this one +EV, based on that assumption. 

Doin’ That Rag 

An early tune that was most definitely written under the influence of LSD (and if it wasn’t, whoa) it features the line “one-eyed jacks and the deuces are wild, the aces are crawling up and down your sleeve” which sure seems like a +EV situation. While you may or may not be in possession of any of the wild cards, having aces “crawling up and down your sleeve” certainly indicates a fine hand of poker. Or, I suppose, taken more literally, it may mean you are tripping your face off and think playing cards are crawling over every inch of your body. I choose the former.

China Cat Sunflower

Another unmistakable LSD-influenced tune (sample lyric: “Copper-dome Bodhi drip a silver kimono like a crazy-quilt stargown”) it also features the following mystical line: “like a diamond eye jack.” I do not know what a “diamond eye jack” is, but I suppose if you draw a jack and you see a diamond for an eye, you’re doing A-OK.

Candyman

Welp, we had a good +EV run, but it ends here. “Come on boys and gamble. Roll those laughing bones. Come on boys and wager, if you have got the mind. If you got a dollar boys lay it on the line.” OK, so far, not terrible. Seems like an even-enough betting situation. But remember: That’s the Candyman speaking, encouraging you to gamble with him, and I don’t know about you, but if anyone who goes by the moniker “Candyman” wants to play dice with me, I am turning tail quicker than you can say “laughing bones.”

Dire Wolf

Levitan may be fearful of a stranger murdering him (key lyric here would be the on-the-nose chorus, “Don’t murder me. I beg of you, don’t murder me. Please, don’t murder me”) but I’d be equally concerned playing cards with a magical wolf, as the protagonist sings, “The wolf came in, I got my cards, we sat down for a game. I cut my deck to the Queen of Spades, but the cards were all the same.” Unless that’s David Blaine in a wolf costume, I’m running out the door.

Stagger Lee

Do not gamble with Stagger Lee. Don’t believe me? “Christmas evening with a full moon over town, Stagger Lee met Billy DeLyon and he blew that poor boy down. Do you know what he shot him for? What do you make of that? ‘Cause Billy DeLyon threw lucky dice, won Stagger Lee’s Stetson hat.” Lucky dice does not mean loaded dice, so it sounds like Stagger Lee lost his hat fair and square, but he killed DeLyon anyway. There is no world in which it is +EV to play dice with Stagger Lee.

Keep Your Day Job

Another rare “on the nose” Dead tune, with the lyrics basically telling people to keep working their 9-to-5 while they try to secure bigger and better paydays. “Maybe you collect or maybe you pay, still got to work that eight-hour day. Whether you like that job or not, keep it on ice while you’re lining up your long shot. Which is to say, Hey-ey.” Sounds to me like Jerry Garcia is personally telling me to keep writing for US Bets despite my certainty I’m going to take down a pair of Milly Makers this coming NFL season. That’s right. Two.

Tennessee Jed

A loopy little song about Jed who’s “bound to wind up dead” unless he heads back to Tennessee, we find the protagonist waking up one morning “feeling mean, went down to play the slot machine.” And what happened? “The wheels turned round and the letters read, ‘Better head back to Tennessee, Jed.’” If only all slot machines were so honest, we’d be better off.

Throwing Stones

“Click flash blade in ghetto night. Rudy’s looking for a fight. Rat cat alley, roll them bones. Need that cash to feed that jones.” Anytime someone is looking for a fight and you’re in need to feed your jones, best to stay out of rat cat alleys. No-brainer. Run away.

Mississippi Half Step Uptown Toodleloo 

Fun song, but very negative EV. Two lyrics stand out: First up, “They say that Cain caught Abel rolling loaded dice, ace of spades behind his ear and him not thinking twice.” I’m no biblical scholar, and I’m reasonably certain this is not how the Cain and Abel story played out, but this just reeks of bad juju. And then, later in the song, “What’s the point to callin shots? This cue ain’t straight in line. Cueball’s made of styrofoam and no one’s got the time.” I have no idea what this means, but again, it doesn’t sound like a game of pool I’d like to wager on.

And finally, the most negative-EV Grateful Dead song is …

Loser

The entire song is about a guy who ain’t winning, and it’s capped off with a final verse that ends like this: “Come to Daddy on an inside straight. I got no chance of losing this time. No, I got no chance of losing this time.” Newsflash: You’re not going to get that inside straight, at least 83% of the time if you’re playing hold’em, and even if you do, there’s no promise of victory. And just saying “come to Daddy on an inside straight” marks you as a loser, ya fish ya.

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