She was born Roberta Lee Streeter on July 27, 1942 near Woodland in Chickasaw County, Mississippi to Ruby Lee (Shipman) and Robert Harrison Streeter. Shortly after her birth, her parents split up and Roberta moved to California to live with her paternal grandparents. At the age of six she relocated to Greenwood, Mississippi where she taught herself how to play the piano by watching the pianist at Pleasant Grove Baptist Church. By the time she was thirteen she moved again, this time to Arcadia, California. It was here that she saw a film called Ruby Gentry,, starring Jennifer Jones, and decided then and there to change her last name. After high school, Bobbie studied philosophy at UCLA and music at the Los Angeles Conservator of Music, supporting herself by doing office work, modeling, and occasionally performing in nightclubs.

In 1966, Bobbie made her recording debut, singing duets with Rock-a-billy artist Jody Reynolds on "Stranger in the Mirror" and "Requiem for Love". Now performing with her own group, she was writing all of the ensemble's material and decided to find a publisher for her songs. She took a demo of "Mississippi Delta"/"Ode To Billie Joe" to music publisher Larry Shayne, who played it for Capitol Records executive Kelly Gordon. After signing her to a contract, Capitol at first intended to release "Mississippi Delta" as Bobbie's first single, as "Ode To Billie Joe" consisted of eleven verses, lasting over eight minutes. After cutting the song down to a run time of four minutes and fifteen seconds and adding four violins and two cellos to the track, the song was now suitable for radio airplay. Believing that they had a hit record on their hands, Capitol invested in a massive marketing scheme to promote the single. Released on July 10, 1967, the record cracked the Billboard Top 40 on August 12 and topped the chart two weeks later. Remaining in the number one position for four weeks, the song also reached #13 in the UK and sold over three million copies around the world. It also garnered three Grammy Awards. The album, "Ode to Billie Joe", replaced The Beatles' "Sgt. Pepper's Lonely Hearts Club Band" at the top of the Billboard 200 LP chart. Bobbie was also named the Academy of Country Music's Most Promising Female Vocalist. The song stirred the imagination of the record buying public, who seemed to be obsessed with knowing what it was that the narrator and Billie Joe McAllister threw off of the Tallahatchee Bridge. Was it a ring, flowers, or even a baby? In later years, Gentry would say that those people were missing the point of the song, which was really about the nonchalant way a family talked about Billie Joe's suicide without realizing that his girlfriend was sitting at their very supper table.

Predictably, Gentry's second album, 1968's "The Delta Sweete" could not equal the success of her first. Two US singles, "Okolona River Bottom Band" and "Louisiana Man", peaked at #54 and #100, respectively, on the Billboard Hot 100. Her third studio album, "Local Gentry" was released six months later, in August 1968. Two singles from the LP, "Sweete Peony" and "The Fool on the Hill", failed to chart. In September of that same year Bobbie was paired with Glen Campbell on the album "Bobby Gentry and Glen Campbell". The effort topped the Billboard Top Country LP chart and reached #11 on the Hot 200. By the end of January, 1969, it had been certified Gold by the Recording Industry Association of America. The album's debut single, "Mornin' Glory", was released in October 1968, and peaked at #32 on the Billboard Easy Listening chart and #74 on the Hot 100. A follow-up release, "Let It Be Me" gave Bobbie her second Billboard Top 40 hit when it rose to #36.

During this time, Gentry made several guest appearances on TV shows hosted by Glen Campbell, Tom Jones, Andy Williams, Carol Burnett, Bobby Darin and The Smothers Brothers. Her fifth studio album, "Touch 'Em with Love" was released on July 7, 1969. The title track was released as the first single, peaking at #113 in America. The second single, "I'll Never Fall in Love Again", was released in August 1969 in Europe and Australia. It peaked at #1 on the UK Singles Chart and #5 on the Australian Kent Music Report Singles Chart. Also included were Jimmy Webb's "Where's the Playground, Johnny", "You've Made Me So Very Happy" and the critically acclaimed "Son of a Preacher Man". Another duet with Glen Campbell, a cover of The Everly Brothers' "All I Have To Do Is Dream", became Bobbie's final Billboard Top 40 entry when it reached #27 in the Spring of 1970. On the personal side, 27-year-old Bobbie had married 58-year-old casino magnate Bill Harrah on December 18, 1969, but divorced on April 16, 1970, only five months later.

"Fancy", Gentry's sixth studio LP, was released in April 1970. The album's title track reached #31 on the Billboard Hot 100 and #26 on the Top Country Songs chart. Three additional singles were released, "Raindrops Keep Fallin' On My Head", "He Made A Woman Out Of Me", and "If You Gotta Make A Fool Out Of Somebody". April, 1971 brought her seventh and final studio album, "Patchwork", and although the critics were more than generous in their praise, record buyers were not so thrilled. The LP could only manage to reach #221 on Billboard's Bubbling Under the Top LPs chart. The albums's first single, "But I Can't Get Back", released in March 1970, peaked at #37 on the Billboard Easy Listening chart and #93 on the Canadian RPM Top Singles chart. In May 1970, "Somebody Like Me" was released as a single in the UK, but did not chart.

In 1974, Bobbie began hosting a summer replacement variety show on CBS called The Bobbie Gentry Happiness Hour. The show was not renewed for a full season. That same year, Gentry wrote and performed "Another Place, Another Time" for writer-director Max Baer, Jr.'s film Macon County Line. By 1976 she was ready to try marriage again, this time to businessman Thomas R. Toutant on August 17. This one would also end in divorce two years later.

In 1976, Max Baer Jr. directed the feature film Ode to Billy Joe, which was based on Gentry's hit song. Starring Robby Benson and Glynnis O'Connor, the $1.1 million production ended up grossing over $27 million at the box office and another ten million from TV, video and foreign markets. A re-recording of the original hit song (#81) and Capitol's re-issue of the original (#88), both made the Billboard Hot 100.

Unfortunately, behind the scenes work in television production could not hold Bobbie's interest. After the 1978 single "Steal Away" failed to chart, she decided to retire from show business. Her final major appearance as a performer came on December 24th, 1978 when she guested on The Tonight Show Starring Johnny Carson. Bobbie had married singer and comedian Jim Stafford ("Spiders And Snakes") on October 15 of that same year, but they divorced in September 1980. The union produced one son, Tyler Gentry Stafford. She has not remarried. Bobbie was last seen on stage on the May 10, 1981 TV special, All-Star Salute to Mother's Day, where celebrities such as Bob Hope, Foster Brooks, David Copperfield and Jamie Lee Curtis honored moms across America.

From 1968 until 1987, Gentry was a part owner of the Phoenix Suns basketball team.

In a 2016 report in The Washington Post, Bobbie was said to be living a quiet life in a gated community in suburban Memphis, Tennessee. Her residence was about a two hour drive from the Tallahatchie Bridge.