For singer/songwriter Bobby Bare Jr., growing up in the shadow of a famous country singer father, Bobby Bare, and family friend Shel Silverstein could have been an ambition-stirring dream or a confidence-crushing nightmare. Luckily for the musician, it seems to have been the former — Bare Jr.’s got seven, almost eight albums under his belt, a busy touring schedule, and a prolific songwriting career that’s showing no signs of slowing down.

Bare Jr. is son to the Grammy award-winning country singer Bobby Bare, who was dear friends with Silverstein. Though he’s best known for being the author of children’s classics like Where the Sidewalk Ends, A Light in the Attic, and The Giving Tree, Silverstein was also a songwriter, penning tunes you’ve probably heard like “A Boy Named Sue,” and “The Cover of the Rolling Stone.” In the 1970s Silverstein wrote the duet “Daddy, What If” for Bare, who sang it with then-six-year-old Bare Jr. It became a huge hit, even earning the two a Grammy nomination.

And that was far from the end of the Bare family’s collaboration with Silverstein. Over the years, Silverstein wrote many songs for Bare, including a 1974 album the singer recorded with his wife and two sons called Singin’ in the Kitchen. The family friendship remained strong until Silverstein died in 1999.

Thanks to that shared history, the poet became an inescapable presence in Bare Jr.’s musical career, which is just the way Bare Jr. liked it. “He critiqued every song I wrote till he died,” he says. “Shel serves as a beacon for what I try to get close to.” Bare Jr. learned a lot about songwriting from watching Silverstein work. “He was diligent about overwriting. You don’t even know most of the verses [in his songs] because he’d edit them down.” Bare Jr. has picked up that habit too, writing more than he needs to so that he can later pare the song down to its very best parts. “I think I just try harder than most songwriters. I try to write poems,” he says. “Lots [of songwriters] will just try to get something that sounds cute enough and stop there.”

That intense focus on language is highly evident in Bare Jr.’s work, especially on his last album, A Storm, A Tree, My Mother’s Head, which was released in 2010. Even the spare title, which refers to a frightening accident that befell his mother, is poetic. There’s no clutter in a Bobby Bare Jr. song, whether it’s a loud rock ‘n’ roll ditty like “Jesus Sandals” or the tragic “One of Us Has Got to Go.” In that straightforward song about a desperate man seeing his ex with her new boyfriend, Bare Jr.’s vocals are accompanied only by simple chords on an acoustic guitar: “Put bullets in the pistol, put the pistol in my mouth / But the barrel did not taste right,” and later, “One is not enough and three is too many / One of us has got to go.” Just hearing it once is enough to make you shiver.

But Bare Jr. is equally comfortable with the absurd and the sweet, which is yet another thing he shares with his former mentor. In addition to lighter songs he’s written on his own, Bare Jr. worked with his dad on a tribute album to Shel Silverstein, tapping musical friends and fellow Silverstein fans like My Morning Jacket, Andrew Bird, John Prine, and Dr. Dog to do covers of poems and songs. “It took up two full years of my life,” Bare Jr. says. “But it was a blast. I sang on or produced more than half of it. It was definitely a labor of love.” The album, called Twistable Turnable Man, was released in 2010 and includes a recording of “Daddy What If” that Bare Jr. did with his own daughter, five-year-old Isabella Bare.

And perhaps that’s one of the most interesting things about Bare Jr. Although he’s come full circle in many ways, returning to the songs and songwriter that he first encountered as a child, he continues to move forward, forging a unique musical path steeped in both acoustic and rock music, tightly controlled poetry, and unabashed noise. He loves both approaches, he says. “I’ll do an acoustic set on stage one night that I think is the best thing I’ve ever done, and then a week later I’ll do some rock and think yeah, this is what I should be doing.”