 A number of reviewers have compared "Dear Jessie" to the work of The Beatles. Allen Metz, one of the authors of The Madonna Companion: Two Decades of Commentary, described the composition of the song as "pastel-pretty, [and] richly orchestrated". He felt that the song would have fit better on The Beatles'1969 soundtrack album, Yellow Submarine. The Beatles influence was also noted by Stephen Holden from The New York Times, who labeled "Dear Jessie" a "stylish swatch of late Beatles-style psychedelia". Joey Levy from Spin characterized "Dear Jessie" as "amazing", describing his reaction to the song as "Wow! This is neat!" He added that the song sounded like Prince singing for The Beatles' 1967 album Sgt. Pepper's Lonely Hearts Club Band. Kevin Phinney from the Austin American-Statesman compared the song to the solo work that Beatles' member John Lennon did later in his career. Phinney wondered how Madonna was able to come up with the song, since most of the tracks from Like a Prayer are full of innuendo and double meanings.
