About The Song
In November 1973 Bobby Bare released the ambitious double album *Bobby Bare Sings Lullabys, Legends and Lies* on RCA Records. The project, largely built around songs by Shel Silverstein, marked a creative breakthrough for Bare after he had returned to the label earlier that year. Among the longer narrative tracks was “Brian Hennessey,” a five-minute-and-forty-six-second story song written solely by Silverstein. The recording fit comfortably into the album’s mix of lullabies, legends, and tall tales, and it later reappeared on the 1976 compilation *The Winner and Other Losers* without ever being issued as a commercial single.
Shel Silverstein crafted the song as a classic O. Henry-style twist tale with a dark, philosophical edge. The story opens with Brian Hennessey sitting back while a toothless gypsy reads his palm. When her eyes grow wide and wild, she whispers a grim prophecy through her gums: he is marked for death and has very little time left. The verses follow Hennessey as he takes the warning seriously, abandoning his wild, wicked ways in an attempt to cheat fate. He tries to live a quiet, virtuous life, hoping to outrun the prediction, but the narrative builds toward an unexpected and bittersweet conclusion that questions what it really means to be “alive.”
Bare delivered the performance with his trademark warm, conversational baritone and unhurried storytelling rhythm. His relaxed phrasing let Silverstein’s detailed scenes unfold naturally, turning the gypsy’s ominous reading and Hennessey’s desperate transformation into something both darkly humorous and quietly profound. The arrangement stayed rootsy and atmospheric, featuring acoustic guitar, subtle percussion, and just enough moody touches to evoke the fortune-teller’s tent without overpowering the narrative voice. Bare’s easygoing delivery made the philosophical twist feel like a late-night tale shared over a drink rather than a heavy-handed moral lesson.
By late 1973 Bare was enjoying renewed artistic freedom after years of label shifts. *Lullabys, Legends and Lies* gave him room to explore longer, more literary material that other artists might have overlooked. The album produced major hits such as “Marie Laveau” and the Grammy-nominated “Daddy What If” with his young son, but deeper cuts like “Brian Hennessey” highlighted Bare’s willingness to embrace complex storytelling. The track stood alongside other Silverstein gems such as “Bottomless Well” and “Rosalie’s Good Eats Cafe,” reinforcing Bare’s reputation as country music’s premier interpreter of intelligent, character-driven songs.
Although it never appeared on the Billboard charts, “Brian Hennessey” quickly became a favorite album cut among fans drawn to Bare’s Silverstein collaborations. The double album itself was a commercial and critical success that introduced his work to new audiences, including college listeners and pop fans who appreciated the blend of humor, heart, and unexpected endings. Over the years the song has remained a cult favorite on reissues and compilations, including Bear Family’s comprehensive eight-CD box set *Bobby Bare Sings Shel Silverstein Plus*.
More than fifty years after its release, “Brian Hennessey” continues to resonate as one of the sharper, more thought-provoking tracks from Bare’s landmark Silverstein period. Its clever twist and philosophical undercurrent capture the spirit of Silverstein’s writing at its most inventive, while Bare’s warm, empathetic delivery makes the story feel both entertaining and quietly profound. The song reminds listeners why Bare’s relaxed style and respect for strong songwriting produced some of the most memorable narrative country music of the 1970s.
What began as one ambitious track on a groundbreaking double album became a lasting example of Bobby Bare’s gift for turning tall tales into something deeper and more human. It stands as a highlight of his creative partnership with Shel Silverstein, proving once again that country music could be funny, dark, and unexpectedly wise all at the same time.
Video
Lyric
Brian Hennessey sat back and let the gypsy read his palm
When he saw her eyes grow wide and wild and dark
And she whispered through her toothless gums and clutched him by the arm
She said, “Boy, I fear I see the devil’s mark”
Brian Hennessey just laughed and pealed the ten-spot from his roll
‘Cause he’d never ever known the taste of fear
But he wondered why the summer nights should suddenly turn cold
As the gypsy’s words come ringing in his ear
“You can run, you can hide, Brian Hennessey”, she cried
“But you can’t escape the fate that’s in your hand
And say, how does it feel to have dealt your final deal
Go on lay down, Brian, you’re a dying man”
Brian Hennessey walked through the doors of the Dining Dog Saloon
Where he stopped to have his nightly glass of gin
And the one-eyed scar-faced stranger a dealing blackjack in the gloom
Winked his ghastly grey glass eye and dealt him in
Brian watched in fascination as the stranger’s fingers flew
Why he’d never seen such cheatin’ done before
And his hand closed round a handle of his snub-nose 32
When the gypsy’s warning come to him once more
“Oh, you can run, you can hide, Brian Hennessey, ” she cried
“But you can’t escape the fate that’s in your hand
And say how does it feel to have dealt your final deal?
Go on lay down, Brian, you’re a dying man”
Brian Hennessey just folded up his cards and walked away
Holding back the rage that burned his soul
And he stopped to have some coffee at the Mockingbird Cafe
But that slender blue-eyed waitress was his goal
And a few words from his silver tongue soon turned her fluffy head
She said, “My husband’s out of town, you need not fear”
But as he pressed her to the softness of her fluffy-feathered bed
On her pillows he saw written bright and clear
Oh, you can run, you can hide, daring letters clear and wide
Said you can’t escape the fate that’s in your hand
And say how does it feel to have dealt your final deal
Go on lay down, Brian, you’re a dying man
Brian Hennessey, he stumbled down the stairs into the street
And from that day on he changed his wicked life
And he never drunk or gambled and he never dealt no dough
And he never touched another fellow’s wife
And years later he met the gypsy when his days were almost done
He said, “Ha, ha, I beat your curse, don’t you know”
But when she saw the frightened, trembling, withered wretch that he’d become
She said, “Brian, you died 20 years ago”
“Because you ran and you hid, that’s exactly what you did
But you didn’t escape the fate that’s in your hand
And say how did it feel to have dealt your final deal?
Go on lay down, Brian, you’re a dying man”