Nearly thirty years after O.A.R. recorded their debut album as high schoolers with no record label, “That Was a Crazy Game of Poker” is still the song most fans point to first. It’s long, strange, split into two completely different halves, and built around a card game with the devil, and the real story behind it is almost as unexpected as the song itself.
It Started With Stephen King
Frontman Marc Roberge has said the seed of the song goes back to middle school, when he became obsessed with Stephen King’s sprawling novel The Stand. He carried a copy around in a leather book cover and reread it constantly, drawn to its scale and its classic wanderer-on-a-journey structure. Around the same time, he’d started writing his own story called “The Wanderer”, the same title that would later become the name of O.A.R.’s debut album.
A Rough Night, Thousands of Miles From Home
The actual song didn’t come together until years later, when Roberge spent a semester of high school abroad in Israel. After a difficult night, he came back to his dorm room needing to write. What came out was the idea of a man being tested over and over in a card game against the devil, raising the stakes of that “wanderer” concept into something almost biblical.
That’s why the song’s first half moves fast: it was written in one sitting, in a single emotional state. The slower, half-time second section, the part with more of an island feel, came later, after Roberge returned to the U.S. and, in his words, had cleared his head and found himself in a much better place.
What actually happens in the song: The narrator loses hand after hand, watching his money, his gold, and everything else disappear across the table, including one brutal beat where a strong full house gets run down by an opponent’s royal flush. But when the devil finally asks for something more than chips, the narrator refuses to hand over his soul, and walks away from the table on his own terms.
Why It Still Gets Called O.A.R.’s Defining Song
“That Was a Crazy Game of Poker” became the band’s breakout track in the jam-band and college-scene underground years before O.A.R. had any mainstream radio presence, largely through word of mouth and heavy circulation of live recordings. It’s shown up repeatedly on the band’s live albums, including Live in Boston and Live from Merriweather, and tends to stretch out even longer on stage than its already-lengthy studio cut.
The song also set the tone for the rest of The Wanderer: Roberge has said its success as a piece of storytelling directly influenced other tracks on the album, including “About an Hour Ago” and “Black Rock,” which continue following a wandering narrator picking up strangers along the way.
Where the Song Sits in 2026
O.A.R. is marking 30 years as a band in 2026 with their Three Decades Tour, and “That Was a Crazy Game of Poker” remains a fixture of the setlist alongside new material like their single “Where We Are Right Now.” For a song written by a teenager alone in a dorm room, it’s held up remarkably well — still one of the most requested deep cuts at every show.
Roberge has described the song as a story about resisting temptation, wrapped inside the shape of a card game gone wrong.
FAQs
1. Who wrote “That Was a Crazy Game of Poker”?
The song was written by O.A.R. frontman Marc Roberge, who developed the idea while he was a teenager.
2. What inspired “That Was a Crazy Game of Poker”?
Marc Roberge has connected the song’s inspiration to Stephen King’s The Stand and a story he was writing called “The Wanderer.” The song later developed into a story about a man playing a high-stakes card game against the devil.
3. What is “That Was a Crazy Game of Poker” about?
The song tells the story of a gambler who repeatedly loses money and possessions while playing against the devil. When the devil ultimately demands his soul, the narrator refuses and walks away.
4. When did O.A.R. release “That Was a Crazy Game of Poker”?
The song appeared on O.A.R.’s debut album, The Wanderer, which was recorded independently while the band was still young and building its audience through live performances.
5. Why is the song considered O.A.R.’s defining track?
Its storytelling, unusual structure and popularity through college and jam-band communities helped make it one of O.A.R.’s signature songs. It has also remained a regular part of the band’s live performances over the years.
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