Freeman was born in the San Francisco Bay Area and spent much of his youth in San Francisco, California. He attended Mission High School. He started singing in a doo-wop group, the Romancers, in his early teens, and first recorded with them for Dootone Records in 1956. Their recordings included "House Cat", included on several later rock and roll compilations. However, the group soon fell apart, and Freeman started a new group, the Vocaleers. When asked by a local DJ if he had written any songs, he wrote several and recorded them as solo demos. These included "Do You Want to Dance", which were heard by a visiting record label executive, Mortimer Palitz of Jubilee Records. He signed Freeman to the label and had the original recording overdubbed in New York by session musicians including guitarist Billy Mure. Released on the Jubilee subsidiary label Josie, "Do You Want to Dance" quickly rose to number 5 on the pop chart and number 2 on the R&B chart in early 1958, when Freeman was still only 17. The song was covered later by Del Shannon, the Beach Boys, Johnny Rivers, Bette Midler, John Lennon, Cliff Richard, Marc Bolan & T.Rex, the Mamas & The Papas, Bobby Vee and the Ramones. Freeman appeared on American Bandstand and toured with such musicians as Fats Domino, the Coasters, and Jackie Wilson. Several of his follow-ups on Josie, including "Betty Lou Got a New Pair of Shoes" and "Need Your Love", a ballad, also made the pop charts. He left Josie in 1960 and signed with King Records, reaching the charts again with "Shimmy Shimmy". However, several of Freeman's later recordings for King in the early 1960s went unreleased, for unexplained reasons. He did not return to the charts again until 1964, after signing for the Autumn label, when he had his second top ten hit with "C'mon and Swim". The song was co-written by label owner and radio DJ Tom Donahue and 20-year-old Sylvester Stewart, later known as Sly Stone, and was produced by Stewart. Freeman's final hit was "S-W-I-M", later in 1964. In 1964 Bobby Freeman played nightly at the Condor Club in San Francisco, where Carol Doda performed her topless go-go dancing shows. Mainly supporting himself as a singer in clubs by the late 1960s, Freeman continued to release singles on various small local labels through to the mid-1970s but met with little commercial success. Freeman performed at the Bay Area Music Awards in later years.. In 1970s, he was noticed among UK northern soul fans.
