[4] As a member of the Pat T. Cake and the Mighty Panthers, Redding toured in the Southern United States, mostly on the Chitlin' Circuit, a string of nightclubs and dance halls hospitable to African-American musicians when racial segregation of performance venues was prevalent.

He signed with Confederate and recorded his second single, "Shout Bamalama" (a rewrite of his "Gamma Lamma"), with his band Otis and the Shooters.

Atlantic Records representative Joe Galkin was interested in working with Jenkins and around 1962 proposed to send him to the Stax studio in Memphis.

[12][14] Rob Bowman, in his book Soulsville, U.S.A.: The Story of Stax Records, wrote that in these two songs "Otis sings with a harsh, impassioned gospel voice reminiscent of Archie Brownlee of the Five Blind Boys of Mississippi" and further reckoned the ending of the first would have made Redding "a superb gospel singer had he chosen to record in that idiom."

[14] The title track, recorded on September, the next year, sparked some copyright issues, as it sounded like Irma Thomas's "Ruler of My Heart".

Rob Bowman observed that "with 'Pain in My Heart,' Otis's dynamic control is front and center as he uses his voice as a horn, swelling and decreasing in volume, swallowing syllables and worrying the word 'heart.

According to Matthew Greenwald of Allmusic, the song is "a stinging, up-tempo groover" and "showed Otis Redding stretching his funky rock & roll roots.

Aided by the usual gang of Stax musicians, it's one of his tightest early records.... [T]he song could have easily succeeded as an instrumental.

[3] A review of several albums by Redding in Rolling Stone magazine observed that "[t]he title track on [Pain in My Heart] set the pattern for all his ballads to come—Otis triumphed at rendering agony.