"Bleeding Heart" is a slow-tempo twelve-bar blues that features Elmore James' vocal and slide guitar.

Personnel Jimi Hendrix, who frequently cited Elmore James as an influence, recorded several different arrangements of "Bleeding Heart".

In 1968, a live version of the song was recorded at a jam session at the Scene Club in New York and later released on several bootleg and gray-market albums, including Bleeding Heart.

On February 24, 1969, a live version was performed by the Jimi Hendrix Experience at the Royal Albert Hall for possible inclusion in a concert film.

Hendrix with the Band of Gypsys recorded a live version of "Bleeding Heart" on December 31, 1969 at the Fillmore East in New York.