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 
Dear Jessie is a brilliant Beatlesque psychedelic orchestral lullaby ballad that set the stage for Madonna’s future songs for her artful students among them Secret, You Must Love Me, Little Star, What It Feels Like for a Girl, Intervention, Beat Goes On and Superstar. Madonna’s role as mother is the most rewarding role of all!