"Mr. Pitiful" was recorded in December 1964 at the Stax Records studios. The song was written by guitarist Steve Cropper and singer Otis Redding, his first collaboration with Cropper, as a response to a statement made by radio disc jockey Moohah Williams, when he nicknamed Redding as "Mr. Pitiful", because of sounding pitiful when singing ballads. Cropper heard this and had the idea to write a song with that name when taking a shower. Cropper then asked Redding in a car how he felt about this idea, and soon after they recorded the song in about 10 minutes. It was finally cut two or three times and then released with the B-side "That's How Strong My Love Is" as a single.