Born in 1942 as Roberta Streeter, country singer Bobbie Gentry was raised by her father and grandparents in rural Mississippi. She wrote her first song, about the family dog, when she was seven. And while she only made a handful of albums, she is remembered today as a pioneer for women songwriters in the music industry.
When she went to live with her mother in California as a teen, Streeter gave herself her stage name, Ruby Gentry (later changed to Bobbie), after the title character in a 1952 Jennifer Jones film. The start of her career was hardly typical of a country star. While gigging at night in Los Angeles and Las Vegas, she studied philosophy at UCLA and then music theory and composition at the Los Angeles Conservatory of Music.
Titan Records signed her to record duets with Jody Reynolds in 1966 after the two had performed some concerts together. While those singles didn’t go anywhere, the experience got her foot further in the door of the music industry. In 1967, things really started happening for Gentry. Her launch to success was made possible by an extraordinary song that she wrote. “Ode to Billie Joe” is a story, almost a prose-poem, that captures in detail a family’s reaction over dinner to hearing about the suicide of a local young man. The more you listen to it, the more you want it to turn into a novel.
Intrigued by the demo, Capitol Records offered Gentry a contract. Soon much of America was listening to Billie Joe’s strange tale. Her hometown in Mississippi named September 30 Bobbie Gentry Day. Taking advantage of the single’s momentum, Capitol named Gentry’s first album Ode to Billie Joe (1967). All but one of its ten tracks were Gentry originals, including the autobiographical “Chickasaw County Child.” Jimmy Haskell wrote the syncopated string arrangements. Her style is a distinctive blend of blues, country, and folk rock.
The success of the first album was in part thanks to the vision of producer Kelly Gordon, who would go on to produce several of Gentry’s albums. He took the helm again for The Delta Sweete (1968). Some critics refer to this record’s style as blue-eyed soul, but soul-flavored country might be the better label. Gentry’s rich, husky voice always sounds as authentic as it is whimsical.
This is a concept album, in a way, exploring many aspects of life in the American South. Writing only about half the tracks herself, Gentry used the opportunity to demonstrate her idiosyncratic taste in songs. The most interesting songwriters often have the keenest ear for other artists’ music, and Gentry was no exception. Among the covers on The Delta Sweete is Mose Allison’s “Parchman Farm.”
Later in 1968, Capitol released Local Gentry. The title came from a Las Vegas show that she and her sisters had developed for Howard Hughes, who owned Caesar’s Palace, where they were billed as the Local Gentry.
Three of the tracks on this album are Beatles covers: “Eleanor Rigby,” “The Fool on the Hill,” and “Here, There and Everywhere.” Her voice is in its prime, dark and complex, which gives the Lennon/McCartney numbers added weight. Gentry shows that she’s learned a lot from the Beatles in “Casket Vignette,” a sardonic and macabre song she wrote about choosing the fabric to line a late husband’s coffin.
Despite all her touring and the residency in Las Vegas, Gentry laid down enough tracks in 1968 to fill a third album that year. This was a collection of duets called Bobbie Gentry and Glen Campbell. Commercially, it was a massive success; artistically, it allowed Gentry to lean into her country roots while giving Campbell – royalty of country music by that time – a chance to explore some material from the contemporary pop world, such as Simon and Garfunkel’s arrangement of “Scarborough Fair/Canticle.”
Two of the singles, “All I Have to Do Is Dream” and “Little Green Apples,” quickly turned into hits. Another fine track, particularly because of its vocal arrangement reminiscent of bluegrass mountain harmony, is John Hartford’s “Gentle on My Mind.”
Gentry’s next solo album, Touch ’Em with Love, followed in 1969. She recorded this one in Nashville, with Kelso Herston as producer. A guitarist and songwriter himself, Herston also worked in the studio with Wanda Jackson and Sonny James. Capitol was keen to push Gentry further into the blue-eyed soul sound and farther from country, since her previous two solo albums hadn’t sold as well as anticipated.
Another change is that only one of the tracks was written by Gentry. But when the covers are as interesting as Jimmy Webb’s “Where’s the Playground, Johnny,” that’s not necessarily a bad thing. Glen Campbell had released this same song as a single just a few months earlier, and had quite a success with it. Gentry’s version did not get the same attention, but her heartfelt singing makes hers the better recording.
Capitol’s attempts to bump up Gentry’s numbers didn’t have much impact on Touch ’Em with Love, but she fared better with Fancy in 1970. This sold especially well in the UK, where country- and blues-tinged pop music was all the rage. Gentry’s own song, “Fancy,” opened the album and was a hit single, as was “I’ll Never Fall in Love Again” (although not as big as Dionne Warwick’s version).
Again, the album includes a lot of worthwhile covers. Among them is Leon Russell’s “Delta Man.” The New Orleans-style arrangement by Tommy Oliver was performed by unnamed session musicians at Rick Hall’s celebrated FAME studios at Muscle Shoals, Alabama.
Patchwork (1971) was Gentry’s seventh album in five years. Capitol was constantly after her to control her style. Music critics seemed to be unable to write about her work without using the word “sexy.” The hassles of the music industry were outweighing the benefits, and this gifted and intelligent woman was reaching the end of her patience. So she committed herself to this one more album.
For the first time, she took on the responsibilities of producer herself and crafted a country album the way she wanted to. She also wrote all the songs herself; one gets a sense of what she would have wanted all her albums to sound like if she’d been in charge of them. The record bombed commercially, but not critically. She had crafted something she could be proud of.
A highlight is “Billy the Kid.” This is not your (great-)grandfather’s “Billy the Kid.” Unlike the 1927 song of that title that Marty Robbins made into a hit, Gentry focuses with dark humor on the anti-hero’s psychology and how society mishandled him.
Gentry was tired of being a celebrity and a sex symbol. Although she continued to make occasional appearances for the next ten years, after Patchwork she never made another record. In 1982, at the age of 40, she officially retired and has kept her life private since then. Her career may have been short, but it mattered a lot.