Dylan is featured on lead vocals, harmonica, and guitar, backed by guitarist Robbie Robertson and an ensemble of veteran Nashville session men.

The song was first released, in shortened form, two weeks after its recording, as the B-side of the single "Rainy Day Women #12 & 35", a Top 10 hit in both the United States and Great Britain.

The song's musical and lyrical influences are thought to include Robert Johnson's "Come on in My Kitchen", "It Hurts Me Too" by Elmore James, and the Mississippi Sheiks classic "Sittin' on Top of the World".

The song has also been covered on tribute albums by artists such as bluesman Luther "Guitar Junior" Johnson, folk musician Greg Brown, and the Americana band Old Crow Medicine Show.

[11][12] Dylan, who was on the North American leg of his 1966 World Tour, arrived in Nashville in mid-February with only a couple new songs in mind and only two musicians from the New York sessions, guitarist Robbie Robertson and organist Al Kooper.

[28] In 1974, Dylan told Maureen Orth of Newsweek that "the singers and musicians I grew up with transcend nostalgia – Buddy Holly and Johnny Ace are just as valid to me today as then.

"[32] However, Daryl Sanders, in his book That Thin, Wild Mercury Sound, points out that Ace's song was a "much slower R&B ballad", differed in style from Dylan's track, and did not include the phrase "pledging my love" in its lyrics.

[2] The song proceeds at a slow pulsing pace set by Ken Buttrey's drumming, with Robertson's guitar and Robbins' piano creating a heavy Chicago blues sound.

[3][33] Gill observes that following the "goodtime goofing" of "Rainy Day Women #12 & 35", the first track on side one, "'Pledging My Time' sets a humid, emotionally oppressive tone for the rest of the album".

[33][34] Dylan's imagery includes the singer's "poison headache," a hobo stealing his lover, the possibility that the relationship may not work out, and the stuffy room where everyone's gone except for him and his girlfriend and he "can't be the last to leave".

[35] In his book Wicked Messenger: Bob Dylan in the 1960s, critic Mike Marqusee writes that the closing verse "hints at a dark betrayal that is both portentous and frighteningly devoid of meaning":[4] Well they sent for the ambulanceAnd one was sentSomebody got luckyBut it was an accidentNow I'm pledging my time to youHopin' you'll come through too.The stanza's "somebody got lucky" offers a distinct clue as to one of the song's inspirations.

[3][4] Ah the woman I loveTook from my best friendSome joker got luckyStole her back againYou better come on in my kitchenBabe it going to be rainin outdoorsOther possible musical influences include the Elmore James classic "It Hurts Me Too" and the Mississippi Sheiks' "Sittin' on Top of the World".

"[40] In his biography, No Direction Home, The Life and Music of Bob Dylan, Robert Shelton wrote that the song was a "slow blues, strong and pulsing, with heavy Chicago influence.

[42] Journalist and author Daryl Sanders praised the musicianship, including Roberson's "biting" guitar work, and Dylan's "dextrous and dynamic harp lines that at times were transcendent".

[49][50][51] In addition, American singer-songwriter Greg Brown recorded "Pledging My Time" for A Nod to Bob, a 2006 album by various artists issued in observance of Dylan's 65th birthday.

[55] In reference to Dylan's film performance of "Pledging My Time", Damien Love of Uncut magazine described him "as casting softly after the shadow of Little Walter", the legendary blues harmonica player.