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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 (JM­6026), 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" (SPS­115) 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 bobbybare.com) RCA Victor. His debut single for the label was 1962's "Shame On Me". Follow-up "Detroit City" reached No. 6 Country, No. 16 Hot 100, [3] 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 further Grammy nominations for Best Country & Western Vocal Performance and Best Country & Western single for the latter song. In 1966, he received a yet another 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 and 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'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".

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 #2 on the country charts, but nearly reaching the Top 40 on the Pop charts. Bare's album, Sings Lullabys, Legends and Lies, became his most commercially successful album, finding him a new audience with pop radio once again playing his songs and also gaining a new following with college kids. These 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 in 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)" (an unusual 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.

Bobby Bare also released a Columbia Record single "Used Car". It was used in the movie of the same name. 

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 low-charting singles.

In 1998, he formed the band, Old Dogs, with his friends Jerry Reed, Mel Tillis and Waylon Jennings.

In 2005, he released his first new album in two decades, The Moon Was Blue, produced by his son Bobby Bare Jr., who is also a musician. He continues to tour today.

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.

After being inducted in the 1960s but gradually drifting away, Bare was reinstated as a member of the Grand Ole Opry on April 7, 2018 by Garth Brooks.

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