Bobby Bare Sings Shel Silverstein Plus: Outlaw Country’s Odd Couple Honored at Last

When it comes to outlaw country, Bobby Bare’s collaborations with Shel Silverstein make even Waylon Jennings’ epochal, Billy Joe Shaver-penned Honky Tonk Heroes LP sound like an Eddy Arnold album of hymns.

That’s why the mighty, eight-CD box set Bobby Bare Sings Shel Silverstein Plus just might be the most historically significant archival collection ever released in the outlaw country realm. At the same time that Waylon was putting out the aforementioned milestone and Willie Nelson was unleashing the equally game-changing Shotgun Willie, Bare’s first album of Silverstein songs, Lullabys, Legends and Lies, was released. It fared far better on the country charts than either of those records, reaching No. 5 and bearing a No. 1 and No. 2 single with “Marie Laveau” and “Daddy, What If?” respectively. But it’s also fully as raw, rebellious, and innovative as Waylon and Willie’s outlaw entrees, and it’s a double album to boot.

Silverstein was a bohemian renaissance man who’d already found success as a cartoonist, playwright, and children’s book author by the time he became famous in country circles by writing the pugnacious 1969 Johnny Cash hit “A Boy Named Sue” and co-writing Kris Kristofferson’s 1971 song “The Taker,” among others. But on the surface, the shaven-headed Jewish polymath from Chicago must have seemed an unlikely addition to the country underground occupied by Willie, Waylon, and Kristofferson in the first half of the ‘70s. 

As a songwriter, Silverstein’s eye for detail and no-holds-barred sense of humor made him a natural fit for the burgeoning outlaw country crowd. Bare’s first cut of a Shel song was a 1972 cover of “Sylvia’s Mother,” a tune that had just been a hit for Dr. Hook. Something clicked between Bare and the baldheaded boy from the Windy City, and by ‘73 it led to the first in a long line of Bare/Silverstein album projects. 

Lullabys’ tall tales of swamp witches (“Marie Laveau”), unbeatable barroom brawlers (“The Winner”), and even Paul Bunyan (“Paul”) mated Silverstein’s loose-limbed wit with Bare’s easygoing grace. Bare took the production reins himself, a highly unusual move for that time. Mirroring Waylon’s contemporaneous m.o. on Honky Tonk Heroes, the let-it-all-hang-out approach was at odds with the current Nashville norms but suited Bare’s natural-man sound all the way down to the ground.

Waylon’s relationship with Billy Joe Shaver was seemingly too volatile to last beyond their one landmark album together, but Bare and Silverstein were like long-lost brothers who’d finally found each other. Over the next decade, their collaborations yielded a big body of work that was by turns touching, funny, scary, and salacious. That last quality really came to the fore with Great American Saturday Night, the unreleased 1978 album that sat on the shelf for decades and is one of this box’s greatest surprises. 

AUDIO: Bobby Bare “Marie Laveau”

Although Bare attributes its initial lack of release to RCA being bitter over his switch to Columbia, in retrospect it’s impossible to imagine any major label in the mid ‘70s (let alone the Nashville-based country arm of one) even considering letting anything like it out the door. The lyrics overflow with profanity, drugs, and sex to an extent completely unprecedented for the time. The title track that opens the album bears a chorus asking, “Anybody here wanna fuck or fight?’ and things only get more transgressive from there.

Speaking of transgession, like a lot of the era’s cultural artifacts, some of Silverstein’s songs are distinctly at odds with contemporary standards of political correctness. Male chauvinism and even the occasional dash of ostensibly homophobic humor pop up at times, but if ever an oeuvre deserved the proverbial grain of salt required by such moments, it’s this one. Bobby and Shel were also able to take the temperature of the nation like nobody else at the time with 1975’s Hard Time Hungrys, a concept album about the toll the era’s tough economic straits were taking on Americans. Nobody ever managed a portrait of poverty with as much homegrown humor as the hard-times handbook “Warm and Free” or the inept bank robber’s plaint “$100,000 in Pennies.”

Nobody could spin a yarn like Silverstein and nobody could deliver one like Bare, and theirs was the perfect marriage. Bare already had a decade of success behind him with more traditional country fare when they first hooked up, but Shel’s songs gave Bare the perfect vehicle for his voice. Bare didn’t just sing a song, he lived it, employing all his natural guy-next-door bonhomie and God-given charisma in a way that seemed deceptively effortless but ranked with the most masterful Shakespearean soliloquy for sheer power of performance.

Bare and Silverstein kept the train rolling all the way through 1983, when Bare took a long hiatus from releasing albums. Together they created a major chunk of the outlaw country canon, but they never really got their proper due for it. For all his successes, Bare never quite achieved the iconic status bestowed on the likes of Willie and Waylon, and the bulk of this material spent too much time out of print. When tales of country outlaws are unfurled, Bobby and Shel frequently get left out of the very story they helped to write. 

At long last, Bobby Bare Sings Shel Silverstein Plus arrives to make things right. Over the course of its eight discs, it compiles every Silverstein song Bare recorded between 1972 and 1983, including a hefty stack of other never-before-heard tracks. And anybody even passingly acquainted with Bear Family’s rep for exquisite box sets will know what to expect from the hardbound book (“booklet” is too diminutive a term) included, which features 128 pages of essays, interviews, lyrics, gorgeous photos, and copious discographic info. 

Not since the 2003 Johnny Cash outtakes box Unearthed have the outlaw country faithful been better served by an ambitious archival set. What we have here, ultimately, is a musical microcosm of America itself — at once poignant, profane, hilarious, horrific, overflowing with quirky characters, and one hell of a ride. 

VIDEO: Bobby Bare Sings Shel Silverstein Plus unboxing