On December 30 1989, Dear Jessie peaked at number-five on the UK singles chart. The track was released as the fourth single from Like A Prayer in Europe (with the exception of France which instead opted to service the North American/Japanese fourth single, Oh Father) and as the fifth single in Australia.
Dear Jessie was written and produced by Madonna and Patrick Leonard and was inspired by Leonard’s young daughter, Jessie, with whom Madonna had developed a special connection.
The psychedelia-infused reflection on childhood fantasy and innocence was particularly poignant within the context of the Like A Prayer album’s sequencing, with its segue into Oh Father offering a stark musical and emotional contrast that is perhaps one of the most effective in Madonna’s body of work.
Today In Madonna History 
Proving she became a mother with Lola, Rocco, David and Mercy, Madonna takes her mother role very seriously-with the same passion she does her music. Like a Prayer was a study in contrast-lighthearted hits such as Cherish and Express Yourself and Keep It Together contrasting with women’s blues and Ciccone hard times-the impassioned #1 hit title cut, Till Death Do Us Part, Promise to Try, Oh Father and Spanish Eyes-not counting the collabs with Prince This Is Not a Love Song and guitar freakout Act of Contrition. Somewhere in the middle was orchestral psych-ballad Dear Jessie-a beautiful Beatles pastiche that appeals to the inner child in all of us! See, Madonna is the gentle type with a tender touch! I love this song! Madonna Forever!