Following the good-time fun of "Rainy Day Women No. 12 & 35", the Chicago blues-influenced "Pledging My Time" sets the album's somber tone. It draws on several traditional blues songs, including Elmore James's recording of "It Hurts Me Too". For critic Michael Gray, the lines "Somebody got lucky but it was an accident" echo the lines "Some joker got lucky, stole her back again" from Robert Johnson's "Come On in My Kitchen", which is itself an echo of Skip James's 1931 recording "Devil Got My Woman". Gray suggests that "the gulping movements of the melodic phrases" derive from the melody of "Sitting on Top of the World", recorded by the Mississippi Sheiks in 1930. The couplet at the end of each verse expresses the theme: a pledge made to a prospective lover in hopes she "will come through, too". Besides Dylan's vocals and improvised harmonica breaks, the song's sound is defined by Robbie Robertson's guitar, Hargus "Pig" Robbins' blues piano and Ken Buttrey's snare drum rolls. The song was released in edited form as the B-side of "Rainy Day Women No. 12 & 35" in March.