Bare had many failed attempts to sell his songs in the 1950s. He finally signed with 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 how to record. Instead of using the version Bill Parsons did later, the record company, Fraternity Records, decided to use the original demo recorded by Bobby Bare. The record reached No. 2 on the Billboard Hot 100, but they made an error: the singles' labels all credited the artist as being "Bill Parsons". The same track, with the same billing error, peaked at No. 22 in the UK Singles Chart in April 1959. In 1965, an album of older recorded material, Tender Years (JM-6026), was released on the Hilltop label. The same material, but under a different cover, was released on the Sears label under the title Bobby In Song (SPS-115) that same year. These albums are not usually included in Bare's published discographies.
Bare's big break in country music came when Chet Atkins signed him to RCA Victor. The first single he released on the label was "Shame On Me" in 1962. His second RCA Victor single, "Detroit City" reached No. 6 Country, No. 16 Hot 100, and in 1964 earned him a Grammy Award for Best Country and Western Recording. Then a surge of hits followed, including "500 Miles Away from Home" (based on a traditional folk ballad written by Hedy West as "500 Miles") and Ian Tyson's "Four Strong Winds". In 1965 he received two Grammy nominations for Best Country & Western Vocal Performance and Best Country & Western single for the song "Four Strong Winds". In 1966, he received a Grammy Nomination for Best Country & Western Male Vocal Performance for his song "Talk Me Some Sense". He also recorded two duet albums with Skeeter Davis and recorded six tracks as a trio with Norma Jean and Liz Anderson which produced a major hit with "The Game of Triangles", a wife-husband-other woman drama that hit No. 5 on the Billboard chart earned the trio a Grammy nomination. In 1968, he recorded an album with a group from England called The Hillsiders. In 1969, he had a Top 5 hit with Tom T. Hall's "(Margie's At) The Lincoln Park Inn".
Bare moved to Mercury Records in 1970 and immediately scored a Top 3 hit with "How I Got To Memphis" and had two Top 10 hits from early Kris Kristofferson compositions, "Come Sundown" (1971) and "Please Don't Tell Me How The Story Ends" (1971). He also scored a No. 12 hit in 1972 with a version of Dr. Hook and the Medicine Show's pop hit "Sylvia's Mother", written by Shel Silverstein.
After two years at Mercury, Bare returned to RCA in 1973 and scored with Billy Joe Shaver's "Ride Me Down Easy" which nearly made the Top 10.
Bare started to release novelty songs recorded live with selected audiences. One such song, "Marie Laveau", reached the No. 1 position on the country chart in 1974; it was his only No. 1 hit. This song was co-written by his friends Shel Silverstein and Baxter Taylor, who received a BMI Award for the song in 1975.
Silverstein penned other songs for Bare including a Grammy-nominated hit, "Daddy What If", which he recorded with his five-year-old son, Bobby Bare, Jr. The song was an immediate success as well not only reaching No. 2 on the country charts but nearly reaching the Top 40 on the Pop charts. Bare's album, "Lullabys, Legends and Lies" became his most commercially successful album and Bare had a new audience with pop radio once again playing his songs and a new following with college kids. These two songs, however, would become Bare's last Top 10 hits. Bare later recorded a very successful album with his family, written mainly by Silverstein, called "Singin' in The Kitchen." It was nominated for best group category in Grammy Awards, but was declined by Bare himself. He continued to record critically acclaimed albums and singles. His biggest hits during this time included "Alimony" (1975), "The Winner" (1976), and "Drop Kick Me Jesus (Through The Goalposts Of Life)" (the world's only Christian-football waltz, and a 1976 Grammy nominee). In 1977 he recorded "Redneck Hippie Romance" and "Vegas" (a duet with his wife Jeannie).
Bare signed with Columbia Records and continued to have hits like "Sleep Tight Good Night Man" a near Top 10 in 1978 and releasing critically acclaimed albums like "Bare" and "Sleeper Wherever I Fall". In 1979, he started off Rosanne Cash's career in a big way by singing a duet with her called "No Memories Hangin' Round" which went Top 20 for them. In 1980, he scored a near Top 10 with "Numbers" which came from his album "Down and Dirty" where Bare started to experiment with Southern rock and continued this with his next album "Drunk and Crazy". In 1981, Bare released an album entitled "As Is" which was produced by Rodney Crowell and returned Bare back to his country roots with songs like "New Cut Road". Bare was still doing well chartwise into the early 1980s. In 1983, he released a Top 30 duet with Lacy J. Dalton called "It's A Dirty Job". His last trip into the Top 30 came that summer with the novelty song "The Jogger".
On 4 February 2012, Bare joined up with Petter Øien at the 2012 Melodi Grand Prix to choose the entry for Norway's entry to the 2012 Eurovision Song Contest to be held in Baku, Azerbaijan, in May. His song, "Things Change", got through to the Norwegian final, held on 11 February 2012. In the final he finished third.
Bare was also given an opportunity to star in movies. He acted in a Western with Troy Donahue, A Distant Trumpet, and a few episodes of the TV series No Time for Sergeants. He turned his back on Hollywood to pursue his career in country music.
From 1983 to 1988, Bare hosted Bobby Bare and Friends on The Nashville Network which featured him interviewing songwriters who sang their hit songs on the show.
In 1985, Bare signed with EMI America Records where he scored 3 charted singles, but none of these reached the upper regions of the charts.
In 1998, he formed the band, Old Dogs, with his friends Jerry Reed, Mel Tillis and Waylon Jennings.
In 2005, he recorded a new album after over 20 years, called The Moon Was Blue, produced by his son Bobby Bare, Jr., who is also a musician. He continues to tour today.
In November 2012, Plowboy Records released Bare's "Darker Than Light", his first LP since 2005. ‘Darker Than Light’ was produced by Plowboy Records co-founder Don Cusic and tracked at famed RCA Studio B in Nashville, with a band that includes Buddy Miller and Randy Scruggs on guitar, Byron House on bass, Marco Giovino on drums and other members of Robert Plant’s Band Of Joy. The album is Bare’s first release in seven years, and features his inspired interpretations of songs by Bob Dylan, Alejandro Escovedo (who also makes a guest appearance), Lead Belly and others, plus new originals. Since then he has appeared on Music City Roots, The Grand Ole Opry and in March 2013, South by Southwest. Find out more at Plowboy Records
In 2012, Bare performed a duet of the song "I'd Fight The World" on the Jamey Johnson album Living for a Song: A Tribute to Hank Cochran.
On April 10, 2013, the CMA announced that Bare would be a 2013 inductee into the Country Music Hall of Fame. Other 2013 Inductees include Cowboy Jack Clement and Kenny Rogers.
In nearly 50 years of making music, he has made many firsts in country music. 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, Shel Silverstein, Baxter Taylor and Kris Kristofferson.A"Daddy, What If" also peaked at No. 19 on the RPM Adult Contemporary Tracks chart in Canada.
BCredited as "Bobby Bare Jr. and 'Mama'."