Kimbrough's debut release was a cover version of Lowell Fulson's "Tramp" issued as a single on the independent label Philwood in 1967.

Kimbrough recorded little in the 1970s, contributing an early version of "Meet Me in the City" to a European blues anthology.

With his band, the Soul Blues Boys (then consisting of bassist George Scales and drummer Calvin Jackson), he recorded again in the 1980s for High Water, releasing a single in 1982 ("Keep Your Hands off Her" backed with "I Feel Good, Little Girl").

[11] The label recorded a 1988 session with Kimbrough and the Soul Blues Boys (this time consisting of bassist Little Joe Ayers and drummer "Allabu Juju"), releasing it in 1997 with his 1982 single as Do the Rump!

This performance was recorded in 1990, in the Chewalla Rib Shack, a juke joint he opened in that year east of Holly Springs to divert crowds from his packed house parties.

[14] Beginning around 1992, Kimbrough operated Junior's Place, a juke joint in Chulahoma, near Holly Springs, in a building previously used as a church.

The album featured many of his most celebrated songs, including the title track, the complexly melodic "Meet Me in the City," and "You Better Run", a harrowing ballad of attempted rape.

His joint in Chulahoma started to attract visitors from around the world, including members of U2, Keith Richards, and Iggy Pop.

Following his death in 1998, Fat Possum released two compilation albums of recordings Kimbrough made in the 1990s, God Knows I Tried (1998) and Meet Me in the City (1999).

[16] Richard Johnston, a Kimbrough protégé, keeps this musical tradition alive with one of Junior's sons, performing live on Beale Street, in Memphis.

His sons Kinney and David Malone Kimbrough, both musicians, kept Junior's Place, which continued to attract big crowds until it burned to the ground on April 6, 2000.