In the fifties after many failed attempts to sell his songs, Bobby Bare finally was signed to Capitol Records and recorded a few rock and roll songs without much chart success. Just before he was drafted into the Army, he wrote a song called “The All American Boy” and did a demo for his friend, Bill Parsons, to learn and record it. Instead of using the version Bill Parsons did later, the record company, Fraternity Records, decided to use the original demo done by Bobby Bare. The record reached number 2 on the Billboard Top 100, but it was wrongly credited to Bill Parsons.

His real big break came when RCA boss and guitarist Chet Atkins signed him to the RCA label. The first song he released on this label, “Shame On Me”, sold nearly a million copies and pushed Bobby Bare to fame overnight.

His second RCA release, “Detroit City” won him a Grammy for the best song of the year. Then a surge of hits followed, including “500 Miles Away From Home”, “Four Strong Winds” and others. He has also recorded two very successful albums with Skeeter Davis and has also duetted with Lacy J. Dalton and Rosanne Cash and additionally had a major hit as part of a trio with Norma Jean (singer) and Liz Anderson in 1967 titled "The Game of Triangles".

He moved to Mercury label in 1970 and had two big hits from early Kris Kristofferson compositions, "Come Sundown" and "Please Don't Tell Me How The Story Ends" before returning to RCA label where he produced his own records. Later Bare moved to CBS label and in 1979, he helped establish Rosanne Cash's career by singing with her on "No Memories Hangin' Round". Bare's singles for Columbia Records included "The Jogger", "Tequila Sheila", "Gotta Get Rid Of This Band", "When Hippies Get Older" and "Numbers”. He later recorded for EMI with little success.

Bobby Bare is a versatile singer, and in the 70s started to release novelty songs recorded live with selected audiences. One of such songs, “Marie Laveau” about a witch, reached the number one position on the country chart. This song was written by his friend, a very talented song writer, poet, author and cartoonist Shel Silverstein. He also penned many other songs for Bobby Bare including a Grammy nominated hit called “Daddy What If” which he recorded with his five year old son, Bobby Bare Jr, who later became a star on his own. Bobby Bare later recorded a very successful album with his family and penned mainly by Shel called “Singing in The Kitchen". It was nominated for best group category in Grammy Awards but was declined by Bobby himself.

He later took chances recording strange, controversial material such as "Dropkick Me Jesus (Through The Goalposts Of Life)" (a 1976 Grammy nominee) and the expletive-driven "Redneck Hippie Romance" with much success.

Bobby Bare also is the first to be given full control of his work and thus the very first Outlaw. In addition, Bobby Bare is credited for introducing Waylon Jennings to RCA. He is also one of the first to record from many well-known songwriters such as Jack Clement, Harlan Howard, Billy Joe Shaver, Mickey Newbury, Tom T. Hall, Kris Kristofferson, and many others. He later had a TV series called “Bobby Bare & Friends, A Songwriter's Showcase”. Recently, he has recorded a new album after over 20 years called The Moon Was Blue, available from Dualtone Records which was produced by his son, Bobby Bare, Jr.

Bobby's track "Are You Sincere" (already considered a classic) from The Moon Was Blue is featured on the Shut Eye release, The United State of Americana, Volume Four.